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Holiday Rentals in Lenox

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    ₹ 18,088 Average
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    ₹ 0₹ 65,000+
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    All 55 Rentals in Lenox
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    INTERIOR DESIGNERS BOTANICAL GARDENS1 / 30
    (1)Excellent
    Lenox
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Heart of Lenox1 / 10
    (1)Excellent
    Lenox
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Heart of the Berkshires!1 / 12
    (2)Very good
    Lenox
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Lenox
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Washer
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    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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    LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE1 / 25
    (1)Excellent
    Lenox
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Mountain Views
    • Private Indoor Pool
    • Hot Tub
    • Air Conditioning
    • Sauna
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 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 01240
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Lenox
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully Furnished and newly renovated condo in beautiful town center of Lenox, Mass. Walk to world class restaurants and be only a short distance from many outdoor activities. Condo is fully furnished with all new furniture . Includes gas fireplace, central AC and heat, Cable and wireless internet...
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    Lenox, Berkshires 01240
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gartner House, a charming home in Lenox1 / 21
    (25)Excellent
    Lenox
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Porch
    • Washer
    • Parking
    • Internet Access
    • Central Heating
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2017
    My teenage daughters, one of their friends and I booked this house for a long weekend getaway. It was just right for us. There were 4 of us, but if we had a couple of more we...
    Reviewed 19 January 2017
    This is the second time my girlfriends and I stayed at Gartner House and we found it just as lovely this time as last. We like staying in to catch up and cook and the house is...
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    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore...
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    Lenox, Berkshires 01240
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Parking
    • Internet Access
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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....
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    Lenox, Berkshires 01240
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Lenox, Berkshires 01240
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The following rentals are within 10 kilometres of Lenox.
    Tranquil 3BR Stockbridge House w/Private Deck1 / 30
    (2)Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Internet Access
    • 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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    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (2)Excellent
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 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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    Location Location Location. Winter Summer Spring or Fall1 / 18
    (6)Excellent
    West Stockbridge
    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 27 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. Visit our web-site aberkshirehome. 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...
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cultural Playground 2 bed, 5 minutes to Tanglewood1 / 25
    (1)Excellent
    Stockbridge
    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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    Berkshire Farmhouse Vacation1 / 20
    (33)Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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...
    Reviewed 31 August 2017
    Our family had a lovely and relaxing time at Elaine’s farmhouse. It is a warm and inviting place equipped with everything that a family could possibly need on vacation. We...
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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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    The Playhouse: 7,000 Sq Feet of Berkshires Luxury1 / 21
    (4)Excellent
    Lee
    6 Bedrooms, 5 Bathrooms, Sleeps 26 Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 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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    Comfortable Farmhouse in the Berkshires1 / 10
    (4)Excellent
    West Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    Nice house, great spot for our family reunion. Convenient to many of the Berkshires attractions. Nice kitchen for cooking and eating in for a group.
    Reviewed 6 June 2017
    House was comfortable and well furnished. The Berkshires are beautiful with lots of activities, galleries, shopping and restaurants. Our hosts were helpful and responsive to...
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    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped....
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    Location Information
    West Stockbridge, Berkshires 01266
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Parking
    • Satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    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 01238
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stockbridge
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • 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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    West Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Mountain Views
    • DVD Player
    • Internet Access
    • Satellite TV
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Boasting 3-acres of beautiful, private land, this 2-bedroom, 1.5-bathroom vacation rental house is nestled in a serene environment, offering pastoral and mountain views. With accommodations for 4, this West Stockbridge home combines comfort and gorgeous scenery to provide the perfect...
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Stockbridge
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Satellite TV
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 1 1/2 to the Red Lion Inn in Downtown Stockbridge, Tanglewood, Norman Rockwell Museum, Private country setting just across from the Housaitonic River. Our newly built home pairs a traditional shingle style exterior with an open & slightly modern interior. The perfect spot to Escape and enjoy...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lee
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Garden
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a completely renovated house that is situated on a private street, 5 min walk to the most beautiful beach on Laurel Lake, as well as 5 min drive to either Lee center or Lenox center. The main floor has an open layout that is full of light. The gourmet kitchen is fitted with top appliances...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Air Conditioning
    • Patio
    • Internet Access
    • Washer
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities in Stockbridge. This quaint vacation rental home features 2 bedrooms and 2 bathrooms, accommodating 6 guests. From this property, you'll be central to all the...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Jacob's Tanglewood Ranch (great for groups 10+)1 / 46
    (2)Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • 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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    little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly!1 / 12
    (1)Very good
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • Porch
    • Parking
    • Mountain Views
    • 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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    Stockbridge Bowl house1 / 11
    (4)Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Central Heating
    • Internet Access
    • Washer
    • 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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    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • 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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    chestnut lodge Queens Room1 / 2
    (1)Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 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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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Writer's Room at Chestnut Lodge1 / 8
    (1)Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Outdoor Dining Area
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Balcony
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine....
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lee
    1 Bedroom, 2 Bathrooms, Sleeps 9 Quick View
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    • Satellite TV
    • Washer
    • Internet Access
    • Parking
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 1-bedroom, 2-bathroom vacation rental house that comfortably sleeps 9! With a spacious loft, private deck,...
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    Lee, Berkshires 01238
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 9
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    Lake House1 / 19
    (4)Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Sauna
    • Air Conditioning
    • Grill
    • Patio
    • Waterfront
    Suitability
    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 01238
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 9
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    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Satellite TV
    • Porch
    • Parking
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    • 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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    Great Vacation House in the Berkshires on Richmond Pond1 / 10
    (3)Excellent
    Richmond
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • 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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    Lakeview cottage with swingset & firepit!1 / 10
    (8)Very good
    Richmond
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • DVD Player
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    • Internet Access
    • 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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    Berkshires Spacious Comfortable Charming Farmhouse1 / 11
    (2)Very good
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Mountain Views
    • Internet Access
    • Parking
    • Satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 01238
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stockbridge
    8 Bedrooms, 10 Bathrooms, Sleeps 17 Quick View
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    • Satellite TV
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Stockbridge, Berkshires 01262
    Private Room - 8 Bedrooms, 10 Bathrooms, Sleeps 17
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    Perfect Getaway for Body, Mind and Soul1 / 24
    (2)Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • DVD Player
    • Satellite TV
    • Washer
    • Hot Tub
    • Internet Access
    • Porch
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat...
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    Lee, Berkshires 01238
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Beautiful New Construction Vacation Home1 / 32
    (5)Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • 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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    Restored 1886 Eyebrow Colonial1 / 17
    (1)Excellent
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • 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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    Berkshire House Share-The Blue Room1 / 10
    (1)Excellent
    Lee
    3 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Share a beautifully renovated home in the Berkshire Mountains of Western MA. I would prefer a long-term housemate, but will be glad to do weekend or short term stays. Long-term pricing can be negotiable. Cable TV (in your room), internet, washer and dryer, big eat-in kitchen, well-lit living room....
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    Lee, Berkshires 01238
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 2
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    Cozy Cottage Private Lake Community1 / 21
    (1)Excellent
    Stockbridge
    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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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Patio
    • Shared Garden
    • Parking
    • Mountain Views
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the second floor of the barn. this is ver rustic, literally a barn! Open cathedral ceiling. Wooden interior with open floor plan. Big queen sized bed with canopy . 2 twin beds. Great for traveling with family or friends. Kitchen area has microwave, mini fridge, induction cooktop, hot...
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    Lee, Berkshires 01238
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 6
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    West Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 at $105/bedroom/night. We...
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    West Stockbridge, Berkshires 01266
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Stockbridge
    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 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1400 square foot, three bedroom home has all amenities including washer and dryer in basement. Electric heat and oven. Front porch and back deck. First floor is open floor plan with kitchen, dining area and living room flowing from one to the other. Skylights in the living/dining area and...
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    Lee, Berkshires 01240
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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!...
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    Lee, Berkshires 01238
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    About this property
    --Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Richmond
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed...
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    Richmond, Berkshires 01254
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Gatehouse on Golden Hill1 / 13
    (1)Excellent
    Lee
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days 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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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Patio
    • Satellite TV
    • Central Heating
    • Porch
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Share a beautifully renovated Victorian home, in downtown Lee, Ma, right in the heart of the Berkshires. Walking distance to town, and on the bus line. Wifi, cable TV, off street parking. Shared kitchen and bath. I have two cats and one other housemate. I am a gospel and blues musician. This is a...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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