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Elder Access Holiday Rentals in Berkshires

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    1 / 13
    5 of 5 bubbles (21) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 10
    5 of 5 bubbles (1) Excellent
    Richmond
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 5
    4 of 5 bubbles (1) Very good
    Pittsfield
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 17
    5 of 5 bubbles (1) Excellent
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Patio
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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... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles 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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    1 / 20
    5 of 5 bubbles (27) Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
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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,... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 bubbles Reviewed 1 week ago
    We enjoyed our stay tremendously. The house is beautiful, very well equipped, spacious and very comfortable. Elaine is so kind and friendly and helped us with all our needs. The...
    4 of 5 bubbles Reviewed 2 January 2017
    This Berkshire Farmhouse worked out great for our 3 family reunion. The house was clean, stocked with plenty of blankets and towels, as well as many other amenities. The owner...
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    1 / 12
    1 of 5 bubbles (1) Terrible
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or... View all property information
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    Great Barrington, Berkshires 01236
    1 / 11
    3.5 of 5 bubbles (4) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 bubbles 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 was...
    4 of 5 bubbles 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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    1 / 12
    4 of 5 bubbles (1) Very good
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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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... View all property information
    Location Information
    Lee, Berkshires 01238
    4 of 5 bubbles 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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    1 / 8
    West Stockbridge
    Private Room, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
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    About this property
    We offer two bedrooms accessible via a private staircase in our recently renovated Victorian farm house located on two beautifully landscaped acres with seasonal gardens and adjoining woods and fields. Each bedroom sleeps 2; they can be booked individually or together. We also offer a continental... View all property information
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    West Stockbridge, Berkshires 01266
    1 / 32
    5 of 5 bubbles (4) Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
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    Becket, Berkshires 01223
    5 of 5 bubbles Reviewed 22 August 2016
    My family and friends - group of 8 just spent an amazing week at this home. The house was a perfect size, clean and fully stocked. We made gourmet breakfasts, lunches & dinners...
    5 of 5 bubbles Reviewed 15 May 2016
    The Levy's home was perfect for our intergenerational family, including a 7month old grandaughter. We were pleasantly surprised by how well the home was supplied and organized...
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    1 / 37
    5 of 5 bubbles (154) Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Mountain Views
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    • Pet-friendly
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    • x
    About this property
    Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B’s. We warmly welcome visitors who come to this beautiful area of Western Massachusetts with or without their companion animals. Now in its sixth year,... View all property information
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    Charlemont, Berkshires 01339
    5 of 5 bubbles Reviewed 3 weeks ago
    My husband and I needed pet-friendly accomodations near Shelburne Falls, MA because we had a morning appointment with Eddie's Wheels for Pets. The staff at Eddie's told us about...
    5 of 5 bubbles Reviewed 3 weeks ago
    We recently spent three nights at the Cavalier Cottage as it is close to our new home and we needed a place to stay before we moved in. The cottage was close to shopping...
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    1 / 32
    5 of 5 bubbles (5) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles 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...
    5 of 5 bubbles 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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    1 / 12
    Lenox
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
    About this property
    This sophisticated ranch is privately sited on a premier road in Stockbridge. Less than a mile to Tanglewood, Stockbridge Bowl, and local theatre companies. Nestled between Lenox and Stockbridge, this is perfect location for your vacation. 3 bedroom and 1 bath, an open floor plan with the guest... View all property information
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    Lenox, Berkshires 01240
    1 / 11
    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
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    Hinsdale, Berkshires 01235
    1 / 16
    5 of 5 bubbles (2) Excellent
    Hancock
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    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... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 bubbles Reviewed 30 July 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to a view of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
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    1 / 23
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Completely renovated 2 bedroom downtown apartment with open floor plan in Lenox MA. Enjoy walks around the downtown area and visit the many attractions in Berkshire County. Endless restaurants to choose from, golf courses within 7 miles, Kennedy Park and Tanglewood close by. Minutes down the road... View all property information
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    Lenox, Berkshires 01240
    1 / 30
    5 of 5 bubbles (3) Excellent
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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.... View all property information
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    Great Barrington, Berkshires 01230
    1 / 21
    5 of 5 bubbles (4) Excellent
    Lee
    6 Bedrooms, 5 Bathrooms, Sleeps 26 | Quick View
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    • Private Garden
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    • Pet-friendly
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    • x
    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... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed 4 weeks ago
    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...
    5 of 5 bubbles 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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    1 / 24
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    I have this in both 1 and 2Br, so please confirm which you want. This is for 1 full week only. Check in is Friday, Saturday, or Sunday, depending upon which week you choose. This is for 1 full week only. Check in is Friday, Saturday, or Sunday, depending upon which week you choose. This is for a... View all property information
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    Hancock, Berkshires 01237
    1 / 23
    Monterey
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only three minute walk to the public beach with life guards on site. In the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about... View all property information
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    Monterey, Berkshires 01245
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    1 / 16
    4.5 of 5 bubbles (2) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Hot Tub
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    • Shared Indoor Pool
    • DVD Player
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    • Satellite TV
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your... View all property information
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    Hancock, Berkshires 01237
    5 of 5 bubbles Reviewed 6 September 2015
    Great location near all outdoor activities including hiking, biking, golf and water sports. Rooms were spacious with 3 TVs. Wi-Fi was fast. One of the poops was heated. Owner...
    4 of 5 bubbles Reviewed 26 October 2014
    Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
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    1 / 16
    4.5 of 5 bubbles (18) Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) **... View all property information
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    Monterey, Berkshires 01245 0933
    5 of 5 bubbles Reviewed 19 November 2015
    I took my wife and three young children up to this house for columbus day week. We had a blast. The house has a real cabin in the woods feel and is just a short walk to the...
    4 of 5 bubbles Reviewed 10 November 2015
    When looking for a house to rent in the Berkshires I began with spots in the towns. However we chose this place due to the reasonable price. As it turned out we liked the remote...
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    1 / 4
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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... View all property information
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    West Stockbridge, Berkshires 01266
    1 / 25
    Lenox
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    • x
    About this property
    220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
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    Lenox, Berkshires 01240
    1 / 21
    4.5 of 5 bubbles (9) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Skiing: Property Is...
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    • Pet-friendly
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    • x
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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... View all property information
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    Hancock, Berkshires 01237
    5 of 5 bubbles 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...
    4 of 5 bubbles 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 and...
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    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This farmhouse has 3 bedrooms available so guests may bring their family, several friends, or overlap with new ones. The Iris Room is bright and airy with 4 windows; the Nasturtium Room has a Full bed with a half bath and the Horse room has a full and single bed across from the community... View all property information
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    Stockbridge, Berkshires 01262
    1 / 26
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bedroom has king bed and master... View all property information
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    Stockbridge, Berkshires 01238
    1 / 21
    Stockbridge
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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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.... View all property information
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    Stockbridge, Berkshires 01262
    1 / 7
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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. Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The... View all property information
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    Hancock, Berkshires 01267
    1 / 13
    Lee
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    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,... View all property information
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    Lee, Berkshires 01238
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    This 1762 farmhouse features wide board floors, kitchen, dining and living room areas along with a spacious front porch. Agritour gardens, horseback riding, and close proximity to Tanglewood and the Norman Rockwell Museum make for an adventure filled visit. Larry prepares a great fresh egg... View all property information
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    Stockbridge, Berkshires 01262
    1 / 6
    Williamstown
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Thanksgiving week Berkshire Luxury condo/4 1Bedroom, 1Bath, Living Room with fireplace & Kitchen Available November 20-27 Thanksgiving week Between Mt. Greylock, Pittsfield, Great Barrington, Stockbridge, Krupalu, Tanglewood, Jacob's Pillow, The Mount, NOrman Rockwell Museum, Daniel Chester French... View all property information
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    Williamstown, Berkshires 01267
    1 / 16
    Lenox
    4 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    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... View all property information
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    Lenox, Berkshires 01240
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    The 1762 farmhouse has 3 bedrooms available to bring your family and friends enjoy the close proximity to Tanglewood, Norman Rockwell Museum, and several lakes, many hiking areas, great restaurants. Larry makes a fresh egg breakfast which is included in your stay. You can join us for horseback... View all property information
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    Stockbridge, Berkshires 01262
    1 / 12
    Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
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    I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!... View all property information
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    Lee, Berkshires 01238
    1 / 31
    Pittsfield
    7 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    This is a beautiful 7 bedroom home with over 4000 sq. ft. of nicely furnished large rooms. Nestled in the heart of the Berkshire Mountains, between 2 lakes and located in a quiet family friendly neighborhood. Just minutes from the New York border. Our home is a fantastic deal for the wonderfully... View all property information
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    Pittsfield, Berkshires 01201
    1 / 35
    Stockbridge
    Private Room, 10 Bathrooms, Sleeps 17 | Quick View
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    Our Stockbridge MA Bed & Breakfast is the closest Inn and within walking distance to the Norman Rockwell and Chesterwood Museums. Nestled on 4 private acres of Berkshires landscape, we offer top quality B&B lodging accommodations that is centrally located to all major area attractions. A Federal... View all property information
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    Stockbridge, Berkshires 01262
    1 / 24
    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the... View all property information
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    Monterey, Berkshires 01245
    1 / 10
    Lenox
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
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    Lenox, Berkshires 01240
    1 / 8
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays and Sundays only. Bentley Brook, located in the Jiminy Peak ski area, offers a variety of on-site amenities -- from downhill skiing to swimming and biking. The Berkshire area also provides a vast... View all property information
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    Hancock, Berkshires 01237
    1 / 13
    Granville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Granville, Berkshires 01034
    1 / 10
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Vacation Village in the Berkshires accommodations feature spacious floor plans for maximum comfort. Kitchen, living and dining room in each suite are integrated for entertaining and enjoyment. Designated suites meet Americans with Disabilities Act (ADA) requirements. Unit Features Individual... View all property information
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    Hancock, Berkshires 01237
    1 / 24
    Lee
    1 Bedroom, 2 Bathrooms, Sleeps 9 | Quick View
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    *Please note that homeowner lives in a separate building on the property and may be present during your stay* Gather your loved ones for a revitalizing Lee retreat when you book this lovely 1-bedroom, 2-bathroom vacation rental house that comfortably sleeps 9! With a spacious loft, private deck,... View all property information
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    Lee, Berkshires 01238
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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Great little house in a very convenient location. Set nicely back from the street with a spacious back and side yard. 8 minutes drive to tanglewood. All rooms are furnished. Living room with bay window and fireplace, hardwood floors throughout. Almost an acre of land with large trees and garden.... View all property information
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    Lenox, Berkshires 01240
    1 / 4
    4 of 5 bubbles (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
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    Hancock, Berkshires 01237
    4 of 5 bubbles Reviewed 11 August 2013
    Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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    Otis
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY... View all property information
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    Otis, Berkshires 01255
    1 / 22
    5 of 5 bubbles (1) Excellent
    Alford
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Wonderful Alford upscale family home with in ground heated pool; art barn, acreage; lush view & privacy. Private tranquil getaway vacation home.Delightful tri-level saltbox which has been completely, thoughtfully & tastefully renovated with every comfort in mind. Main floor: Enters into a breath... View all property information
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    Alford, Berkshires 01266
    5 of 5 bubbles Reviewed 3 weeks ago
    The screen door to the patio stuck a little. That's it. Period. Otherwise, this place was perfect! Three adults (two seniors), two children, and one dog spent a spectacular week...
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    5 of 5 bubbles (1) Excellent
    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect... View all property information
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    North Egremont, Berkshires 01230
    5 of 5 bubbles Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
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    New Marlborough
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Let this serene lakefront Great Barrington area cottage in New Marlborough, within the Berkshires, serve as your ultimate home-away-from-home! Featuring 2 bedrooms, 1-bathroom, and room to comfortably sleep 4 guests, this property is an excellent choice for people who are looking for either a... View all property information
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    New Marlborough, Berkshires 01230
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    Tyringham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English... View all property information
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    Tyringham, Berkshires 01264