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Holiday Rentals near Tanglewood

West St off Rte 183, Lenox, Massachusetts 01240
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    Travellers to Lenox are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 36 Rentals in Lenox
    Gartner House, a charming home in Lenox1 / 42
    (34)Excellent
    2.6 kilometres from Tanglewood
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Heart of Lenox1 / 7
    (2)Excellent
    2.7 kilometres from Tanglewood
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2.4 kilometres from Tanglewood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    4.0 kilometres from Tanglewood
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    Quintessential Lenox Farmhouse with 1881 charm and a shiny new finish. Lovingly renovated and restored, this house is nestled on 4.5 private acres within minutes of the town of Lenox and Tanglewood. The house boasts a chef's Kitchen with all new stainless steel appliances, large farmhouse porcelain...
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    Lenox, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.5 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Enjoy leisurely lakeside days just a walk away as you stay at this 3-bed, 1.5-bath vacation rental house that sleeps 6 in Stockbridge! With mossy grounds below and age-old oaks towering above, this cozy cottage is a dreamy retreat, perfect for those looking for a bit of the great outdoors without...
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.2 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Situated in the heart of the Berkshires, this 3-bed, 2-bath vacation rental offers a modern living space, a large yard and an ideal location near many attractions. Adventure seekers will enjoy easy access to the Appalachian Trail and Catamount Ski Resort, music fans can catch the Boston Symphony...
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    RANKED #1 for 5 STAR REVIEWS covering 354 properties.1 / 50
    (31)Excellent
    3.0 kilometres from Tanglewood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood1 / 32
    (19)Excellent
    1.8 kilometres from Tanglewood
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Lenox, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    A Small Oasis in the Heart of Lenox1 / 6
    (49)Excellent
    2.5 kilometres from Tanglewood
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lenox, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Fox Hollow Laurel Lake Ranch1 / 16
    (1)Very good
    3.8 kilometres from Tanglewood
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    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
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
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    2.0 kilometres from Tanglewood
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Lenox, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    3.6 kilometres from Tanglewood
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
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    • Housekeeping Included
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    Lenox, Berkshires
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Heart of Lenox Walk to Town Cozy Cottage!1 / 14
    (9)Excellent
    2.7 kilometres from Tanglewood
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Lenox, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Berkshires Escape located on a secluded neighborhood1 / 21
    (1)Excellent
    5.6 kilometres from Tanglewood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Comfortable, Luxury Lenox Vacation Home on Miraval/Cranwell Spa & Golf Resort1 / 22
    (3)Excellent
    3.9 kilometres from Tanglewood
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
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    Lenox, Berkshires
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
    Walk to downtown Lenox and Tanglewood in this super charming home.1 / 20
    (19)Excellent
    1.7 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE1 / 19
    (1)Excellent
    3.8 kilometres from Tanglewood
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Mountain Views
    • Private Indoor Pool
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 2017
    My wife booked this property for a couple of days for my birthday celebration. Howard is extremely accommodating the house came with everything! His employee Keith did...
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    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...
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    Lenox, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    'Fall' in love with the Berkshire or 'Winter in !!!1 / 18
    (7)Excellent
    4.8 kilometres from Tanglewood
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
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    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2018
    The house was so comfortable; the location was perfect -- close to so many beautiful places and Berkshires attractions, especially Tanglewood!; Cassandra was so helpful when I...
    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...
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    About this property
    Enjoy this perfectly located home to pursue what brings you to the Berkshires. Ski and warm up next to the fire in the winter. Go to Kripalu but enjoy all the comforts of this home just 8 minutes away. Enjoy fabulous foods, and make new friends. Located in West Stockbridge minutes from everything ....
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    West Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Berkshire Farmhouse Vacation1 / 20
    (42)Excellent
    6.6 kilometres from Tanglewood
    5 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    • Central Heating
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2019
    We stayed in the Berkshire Farmhouse during our winter school break as a large group of 9 with adults and children (including teenagers). Very comfortable, clean, cozy and warm...
    Reviewed 23 September 2019
    We are 4 women in our 70's and 80"s who have been going away together for one week a year for the past 33 years. This year we decided to go to the Berkshires. The...
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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
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 15
    3.0 kilometres from Tanglewood
    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...
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    West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Berkshires Spacious Comfortable Charming Farmhouse1 / 12
    (2)Very good
    6.4 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
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    Pet friendly
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    Reviewed 18 June 2013
    This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on...
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    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock...
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    Lee, Berkshires
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Lake House1 / 18
    (5)Very good
    5.0 kilometres from Tanglewood
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2016
    My family and I traveled to the Berkshires from Boston and stayed in this gorgeous lake house. We had booked vacation rentals in the past and had a whole range of experiences...
    Reviewed 2 September 2016
    We stayed at the Lake House on beautiful Laurel Lake with my family of 5 (two daughters, son, and my wife). We had an awesome time. The owners Marjorie and Frank were wonderful...
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    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home has 4/5 bedrooms and one is equipped as a nanny suite or teen haven. It is close to skiing, golf, outdoor sports, shopping, and all cultural venues. It is located...
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    Lee, Berkshires
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 9
    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (3)Excellent
    2.6 kilometres from Tanglewood
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 18 August 2019
    Great location - quiet, private, and felt like our own little home. Close to the lake with the beach. Only 4 minutes drive to Tanglewood.Next time I visit I will sure look to...
    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
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    2.4 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    6.6 kilometres from Tanglewood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    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...
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    Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Tranquil 3BR Stockbridge House w/Private Deck1 / 30
    (2)Excellent
    6.6 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.5 kilometres from Tanglewood
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    7.3 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    *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 3-bedroom, 2-bathroom vacation rental house that comfortably sleeps 10! With new furnishings, a private...
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    Lee, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    5.5 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Completely renovated vacation home with state of the art kitchen and marble baths, centrally located in the Berkshires 3 miles from Tanglewood, on 10 acres on a quiet country road. New in-ground pool surrounded by patio and expansive deck and pool house nestled in the woods. Central air...
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    Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.6 kilometres from Tanglewood
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Garden
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    About this property
    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...
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    Stockbridge, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    5.3 kilometres from Tanglewood
    4 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 15
    6.6 kilometres from Tanglewood
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    19 Century New England classic home renovated to maintain is historical look and feel but with modern kitchen and bathrooms
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    Lee, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    7.2 kilometres from Tanglewood
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
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    Richmond, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    5.7 kilometres from Tanglewood
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Stockbridge, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.6 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the serene beauty of the Berkshires and stay at this bright and cozy 2-bed, 2-bath cabin! Nestled just a few steps from the Stockbridge Town Beach, the vacation rental is perfectly located for enjoying the area's top attractions, like lake activities, Tanglewood, the Norman Rockwell...
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    Location Information
    West Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    7.1 kilometres from Tanglewood
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home that located between Lenox and Stockbridge. Minutes from Downtown Lee, Stockbridge and Lenox. Nice yard, two car Garage and plenty of parking. Home offers an open floor plan for the kitchen and living room along with four bedrooms, and two full bathrooms. There is a State forest...
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    Location Information
    Lee, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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