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Berkshires Villas

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    Travellers to Berkshires are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 138 Rentals in Berkshires
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    Berkshires Vacation Rental - Bentley Brook Resort Suite1 / 16
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Heart of the Berkshires!1 / 12
    (2)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Wyndham Bentley Brook1 / 19
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Great Vacation House in the Berkshires on Richmond Pond1 / 10
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    This comfortable, breezy house was perfect! We loved being able to walk to the lake and canoe, play frisbee on the lawn, walk in the woods, eat on the deck, and gaze at the...
    Reviewed 29 July 2017
    This house is well quipped with everything you need. It is conveniently located close to beaches with sandy bottoms. Both supermarkets are restaurants are nearby.There are many...
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    About this property
    Beautiful two bedroom house sits just steps from Richmond Pond. Enjoy a day on the water swimming and fishing followed by an evening enjoying the symphony at Tanglewood (ten scenic minutes away). Yoga enthusiasts will love the proximity to Kripalu (again, ten minutes away). Leaf peepers and skiers...
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    Richmond, Berkshires 01254
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    PanoramicView1000 sq ft Guest Quarters Berkshires1 / 16
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Mountain Views
    • Washer
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to aview of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
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    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer...
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    Hancock, Berkshires 01237
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Lakeview cottage with swingset & firepit!1 / 10
    (8)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2017
    The spot is on a wonderful lake - we would like to come back for a longerstay. The cottage was just as described. Our main objective was seeing two Tanglewood concerts...
    Reviewed 27 October 2015
    Better directions to the house would have been helpful. For two nights my daughter and two granddaughters joined us and found the yard and swingset fun. The weather was quite...
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    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view...
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    Richmond, Berkshires 01254
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Stockbridge Bowl house1 / 11
    (4)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Central Heating
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Mountain Views
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2016
    The Stockbridge House was exactly what we expected from the description and pictures. The home is rustic and cozy, like a cabin in the woods. Having water access to the bowl...
    Reviewed 15 July 2015
    Those who used the cottage this week ranged from me alone to one night with eight people for one night. Sleeping was not a problem. The house is ideally located between Lenox...
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    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard.
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Berkshire Farmhouse Vacation1 / 20
    (34)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    Elaine was a pleasure to communicate with and made us feel right at home. The home is just how it looks in the pictures. If you're searching for a comfortable, clean, and cozy...
    Reviewed 3 October 2017
    My family and myself enjoyed our stay at Elaine's rental home. There are many things to do in the area; hiking, shopping, biking, just to name a few. We all had a great time...
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    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,...
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Tranquil 3BR Stockbridge House w/Private Deck1 / 30
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    The degree of care of the owners to assure a pleasant experience was incredible! There was a many page guide to the house, the property and the surrounding area. It...
    Reviewed 24 October 2016
    Awesome setting and a great outside porch complete with herb gardens(2). The forest around the property just invites a hike. Every possible thing was thought of by these...
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    About this property
    Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6 and boasts a private deck. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat. THE PROPERTY...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful New Construction Vacation Home1 / 32
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2017
    Our 4 families stayed here for a long ski weekend and had the best time! The home is beautiful-- and had plenty of space for all of us! The home was fully stocked with...
    Reviewed 10 November 2016
    Excellent experience. Very spacious and beautiful. Amazing backyard woods. Beautiful scenery within and around the town. Very attentive owners.
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    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Berkshires: Romantic Cottage with spectacular view1 / 13
    (22)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    We loved visiting the Berkshires, and the cottage was a perfect romantic heart of our vacation. The scenic views right from the cottage, the pool a few steps away, and great...
    Reviewed 5 August 2016
    What a charming, relaxing, and peaceful rental in the very heart of Berkshires cultural activities and venues. The view and pool are splendid, the apartment itself is private...
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    About this property
    Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows.....
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 December 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living...
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    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2200sf Country House on 16 Acres-2 Miles to Jiminy1 / 14
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Mountain Views
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy...
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    Hancock, Berkshires 001237
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in the area, and soak in the...
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    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Apple Cottage1 / 10
    (4)Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Balcony
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2016
    Our family of four (two adults and a 12 and 8 year old) recently stayed at Apple Cottage with my sister who lives in Boston and had a wonderful week. The house was perfect for...
    Reviewed 16 May 2016
    Tucked away down a country road, farm fresh eggs for breakfast, wonderful rustic cottage details everywhere, Apple Cottage does not disappoint! The cottage easily accommodated 7...
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    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and...
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    Sheffield, Berkshires 01257
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2017
    Location was fantastic. Sarah (the owner) provided some great advice on local farmers markets and hikes. The beach was a quick walk from the cottage where we could paddle on...
    Reviewed 31 July 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
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    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Serene Lakefront Cottage1 / 21
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Waterfront
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2016
    We stayed for a week with two teenaged boys and two dogs. We had a wonderful time. The lake was fully accessible and the boats and life vests well cared for. The photos are...
    Reviewed 2 September 2015
    My husband and I plus our two dogs recently took one last family vacation before our first son arrives later this year. We were looking for a private and peaceful place where we...
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    About this property
    Pretty cottage in the woods on a beautiful private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe or fish from the back yard, or just lounge...
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    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Jacob's Tanglewood Ranch (great for groups 10+)1 / 46
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2017
    Excellent location to enjoy the best of the Berkshires, and a comfortable, spacious house full of historic character. 3 wood burning fireplaces and a screened porch make this...
    Reviewed 30 May 2016
    My family loved this house - parents and kids, all found it comfortable, spacious, and welcoming. Host is accommodative on last-minute changes or special requests. Easy...
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    About this property
    In the heart of the Berkshires: near Tanglewood, Jacob's Pillow, Jiminy Peak, Ski Butternut, Lenox MA, Stockbridge MA. Completely restored historic house with fully equipped kitchen, 5 bedrooms (each with a private bathroom), 3 spacious common rooms. A comfortable place for a family reunion,...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 20
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    INTERIOR DESIGNERS BOTANICAL GARDENS1 / 30
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Private Garden
    • Patio
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2017
    We have been traveling to the Berkshires for several years to attend Shakespeare & Company plays. We have stayed at Inns and Hotels. This was our first time, in this area...
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    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- HAS A SOFA SLEEPER TO ACCOMMODATE 2 MORE GUESTS. KITCHENETTE W/ LG CEILING...
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    Lenox, Berkshires 01240
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    The Playhouse: 7,000 Sq Feet of Berkshires Luxury1 / 21
    (4)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 26 Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 April 2017
    First impressions were that it was amazing as the description - real wow factor. Equipped with everything you could want. The socialising space was amazing, with room for all 19...
    Reviewed 21 December 2016
    The Playhouse provides all that is necessary to have a fabulous time with family or a large group. I have looked for a place to hold our annual family Christmas gathering for...
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    About this property
    220 acres with yoga studio and lakefront. Built by Westinghouse and then part of the Vanderbilt Estate, The Playhouse is a newly renovated iconic Berkshire's property that once served as a theater space for America's greatest innovators, and is now hung with fine art, and includes an in-house yoga...
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    Lee, Berkshires 01238
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 26
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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Parking
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    • Outdoor Dining Area
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    • Internet Access
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,...
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    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Heart of Lenox1 / 10
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Parking
    • Air Conditioning
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2017
    Title sums it up! Excellent choice for our recent visit to Lenox. The house is very clean and comfortable and the owners are very accommodating. Location is great, just steps...
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    About this property
    Just rated Best Small Town in the Northeast by USA Today, our home is located in the heart of Lenox MA! Come relax in our lovely home, situated in a quiet neighborhood just steps from downtown. Walk to Zagat rated restaurants, shop unique boutique shops, hike in Kennedy Park. Whether you love the...
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    Lenox, Berkshires 01240
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Restored 1886 Eyebrow Colonial1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2017
    Our family of four absolutely loved our stay in Melanie and Henry's home. After communicating with Melanie before our arrival, we felt welcome before we stepped into the house...
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    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities. You will be central to all the wonderful cultural attractions and outdoor activities in the area. Walk to the quaint town of Stockbridge and the Norman Rockwell...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy Cottage Private Lake Community1 / 21
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    Quaint Berkshire cottage in great location. Beautiful gardens and access to private community beach. Thank you to our hosts for a perfect week!
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    About this property
    Our cottage is situated in a private lake community. Short walk to lake and private beach. Minutes from Tanglewood, Kripalu, Stockbridge town center and Lenox town center. Convenient to many cultural institutions, hiking, skiing. Our cottage has plenty of outdoor space for relaxing and dining....
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Quiet Comfortable Cabin 5 Min. Walk to Lake1 / 13
    (13)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2017
    The location was easy to get to (even in the dead of winter).The place was clean, spacious and exactly as described. The wood stove was a great heat source as it was really cold...
    Reviewed 26 October 2016
    A charming cozy cottage in a quiet setting with all you need for comfort included. We hiked, canoed and visited farms and museums close by. It was a lovely fall getaway!
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    About this property
    Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful,...
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    Location Information
    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Gatehouse on Golden Hill1 / 13
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Stayed for 4 nights. Very spacious and well maintained. Greeted by Peter with prosecco, cheese, crackers,tomatoes, mint from the garden, and donuts. He gave us an orientation...
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    About this property
    We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the 'Gatehouse' to upscale Erskine Park, this truly one of a kind Craftsmen inspired home is filled with unique features and materials seldom found including eucalyptus and Brazilian Cherry flooring,...
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    Lee, Berkshires 01238
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly!1 / 12
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • Porch
    • Parking
    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2016
    We stayed at Jo-Anne's cottage for a week in mid-July. Wasn't sure what to expect as the place had no reviews. Our hostess made us feel at home right away and made a major...
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    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 2 nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full...
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    Lee, Berkshires 01238
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Indoor Pool
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps from the main lifts this 3 Bedroom unit can accommodate up to 8 guests; with all the comforts of home. Master bedroom, with Queen-size bed, wall mounted TV, large closet and a view of the Cricket lift and learning slope. The master bath has duel sinks, jet tub, body sprays and washer and...
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    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Sauna
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Ski-in and Ski-out your front door! Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking, horseback riding,...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    220 acre Fox Hollow Estate with 1000 feet of Lake Front on Laurel Lake. 8 Person Hot tub on deck. Fabulous deck fire pit, outdoor furniture and gas grill. Fireplace to warm up by. High ceilings, open living concept. 2400 sq. feet with 4 BR's on main level each with private bath, TV and DVD. 3...
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    Lenox, Berkshires 01240
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
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    Apartment walking distance to Mass MoCa!!1 / 22
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2015
    Owners were very friendly and helpful. We enjoyed our stay very much. this is the place for a quiet vacation.
    Reviewed 7 July 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
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    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa (about a 10 minute walk)!!! Animals are welcome if needed. The master...
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    North Adams, Berkshires 01247
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    RiverSong Suite In The Berkshires1 / 52
    (13)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Riversong suite was wonderful, situated in a great location. Close to nearby restaurants and shops yet far from all the noise. Peaceful and quiet. A great place to renew...
    Reviewed 25 August 2017
    Beautiful place, lovely accomodations, wonderful landscape abounds, and very nice and warm hosts. Very comfortable, spacious and private.
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    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,...
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    Location Information
    North Egremont, Berkshires 01230
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Wyndham Bentley Brook at Jiminy Peak1 / 21
    (9)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    • Sauna
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 March 2015
    This is such a great property. We had a one bedroom unit which was still sufficient for 2 adults and 3 teens. Gorgeous large double bedroom with full bath and murphy bed and...
    Reviewed 27 January 2015
    Always a great trip for Friends and family. Easy quick park and party. They have a movie theater activities for kids all day long indoor outdoor swimming pool hot cider coffee...
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    About this property
    Wyndham Bentley Brook Rental includes: King bed master, 2 doubles in the 2nd bedroom, queen sleep sofa, full living room, dining room and kitchen with utensils. New York + New Jersey Flock to Hancock Mass/Jiminy Peak Ski Area, rated Top 5 Family Mountains in the Northeast! Wyndham Bentley Brook...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cultural Playground 2 bed, 5 minutes to Tanglewood1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Parking
    • Patio
    • Grill
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 November 2016
    Me & my son Josh had a lovely stay at the cottage. Ruth was very pleasant, the place was clean and the location was perfect. We were provided with wood for fire, the kitchen...
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    About this property
    This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en-suite bathroom and a bonus...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Shared Indoor Pool
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please email or call to confirm availability. Ski-In/Ski-Out Resort! Wyndham Bentley Brook is located right at the base of Jiminy Peak ski mountain, with ski lifts only 200 feet from the resort's front door. In winter, you can ski right out the door to the lifts. In spring, summer and fall,...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Berkshire Mountain Lodge - Fri, Sat,Sun check ins only!  Inbox x1 / 5
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2017
    We traded in from RCI and had a great stay! The staff and grounds were fantastic. I trade all over the US, and this place is quiet and clean. Boston is only a couple hours...
    Reviewed 19 June 2017
    We Loved the Berkshire Mountain Lodge. Just got back yesterday. We stayed for seven nights. It is quiet as all the rooms consist of one bedroom, living room, large bathroom and...
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    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Located near Lenox, Massachusetts and among the picturesque Berkshire highlands lies the Berkshire Mountain Lodge. Ideal no matter the season, Berkshire Mountain Lodge offers a...
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    Pittsfield, Berkshires 01201
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Sauna
    • Patio
    • Balcony
    • Mountain Views
    • Hot Tub
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless recreational activities and many of the comforts of home. Lounge or swim in the indoor or outdoor pool. Go hiking, biking, fishing or horseback riding around the property or enjoy the off site...
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    Hancock, Berkshires 01267
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Lake House in Berkshires1 / 21
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
    • DVD Player
    • Wi-Fi
    • Parking
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2017
    Robert was so thoughtful and courteous to make sure we had the best birthday weekend ever! He literally thought of everything such as bug spray, flash lights, birthday candles...
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    About this property
    Charming studio cottage on Windsor Lake, North Adams, MA. Great spot from which to explore MASS MoCa, attend Solid Sound or Fresh Grass, Clark Art Museum, Massachusetts College of Liberal Arts, Williamstown Theater Festival, Williams College, the Berkshires, and Southern Vermont. Hike, bike, swim...
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    Location Information
    North Adams, Berkshires 01247
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Hoilday at this Wonderful House.  To ski or not to ski!  Relax by the fire.1 / 18
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2016
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
    Reviewed 2 November 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and...
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    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is a destination, a haven, a state...
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Retreat in the Woods1 / 6
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Grill
    • Hot Tub
    • Parking
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    My husband and I vacationed in the Berkshires to hike and visit the MA state parks. This home is conveniently located within a 30 min. drive to many state parks and hiking...
    Reviewed 20 July 2017
    Lovely home - the pictures don't fully do it justice! The house is shielded from the road and set in a small clearing, so it gets plenty of light and a pleasant breeze at night...
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    About this property
    Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and...
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    Savoy, Berkshires 01256
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Romantic Berkshire Cottage on Storybook Estate1 / 10
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    • Cable/satellite TV
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2017
    What a wonderful, magical place, heaven on earth! From the moment we were greeted warmly by Denise and entered our Tiny House, we knew this was such a special place.The sound of...
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    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest...
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    Tyringham, Berkshires 01264
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Stone School Cottage1 / 10
    (15)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Outdoor Dining Area
    • Central Heating
    • Mountain Views
    • Internet Access
    • DVD Player
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2016
    Private and peaceful. Located where many cultural activities are available.Caring hosts.Our 2nd year!
    Reviewed 13 February 2016
    My boyfriend and I celebrated my birthday weekend at the cottage. We had a rough start the day we were to arrive and Cheryl was just wonderful and so understanding. We were...
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    About this property
    If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. We are about 8 minutes away from Jiminy Peak and...
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    Location Information
    Lanesboro, Berkshires 01237
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    chestnut lodge Queens Room1 / 2
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 17 August 2015
    I had the pleasure of staying at the Chestnut Lodge in the Queen's room. From the moment you step into the foyer you are taken back to a simpler time in this historic lodge. The...
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    About this property
    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2' would be...
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    Location Information
    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 1 Bathroom, Sleeps 15 Quick View
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    • Patio
    • DVD Player
    • Central Heating
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located at the end of a dead end street. It has a huge, private backyard with 2 firepits, hammock, portable bar, grill and ample seating. Under one mile to downtown North Adams and about a 5 minute drive to Williamstown. This is a 3 bedroom, upstairs apartment (one bedroom has a...
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    North Adams, Berkshires 01247
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 15
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (3)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sparkling, newly renovated 3 floors house is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood, Butternut ski, etc The house has an open floor plan, making each room flow into another....
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Balcony
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully appointed and immaculate 5,000 sq. ft. Becket Woods Contemporary sleeps 12 and is the perfect retreat for family and friends. The magnificent main level open floor plan is flooded with natural light and includes: • Romantic master bedroom suite, with its own deck, king bed, large...
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    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS CUSTOM BUILT HOME is a one-of-a-kind, must see getaway retreat that is beautifully furnished, and meticulously maintained. The entire first floor 'guest suite' was designed to accommodate friends or extended family. The upper level is the main floor with an open plan kitchen, dining room, and...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    The Smith Farm Homestead1 / 12
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 February 2017
    Cozy and pretty room and bathroom suite that I shared with my teenaged daughter. Susan is very welcoming and friendly. We loved our stay here and would return!
    Reviewed 17 October 2016
    This is a terrific B&B. Lovely, spacious, comfortable room looking out over rolling pastures and forest. Fabulous breakfasts delivered to your room in a basket: fresh baked...
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    About this property
    The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural...
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    Alford, Berkshires 01266
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Short Walk to Lake, Peaceful Getaway, Scenic Views1 / 13
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Housekeeping Included
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    The rental was spacious, immaculate and very comfortable and it's situated in a very private and relaxing part of the forest.
    Reviewed 25 July 2017
    Just what the doctor ordered. Beautiful, peaceful getaway in a lovely private community. Comfortable beds, great kitchen, would DEFINITELY stay again.
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    About this property
    Would you like to spend some time in our cozy retreat in the Berkshires? Our three-bedrooms, two bathrooms house is located in a private community, in the middle of the Tolland state forest , surrounded by the woods and lakes, but at the same time close to major attractions. Fully renovated, the...
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    Location Information
    Granville, Berkshires 01034
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Mountain Views
    • Patio
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this quaint 2-bedroom, 2-bathroom Hancock condo, which sleeps 6, be the perfect destination for your New England escape! Nestled along the scenic border of New York and Massachusetts in the beautiful Berkshire Mountains, this pristine Hancock vacation rental condo comfortably accommodates 6...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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