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Villas and Houses in Lenox, MA and nearby

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    1 / 16
    Lenox
    4 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    1 / 23
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 25
    Lenox
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    1 / 21
    5 of 5 bubbles (25) Excellent
    Lenox
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Porch
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    • ?
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    • x
    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... View all property information
    Location Information
    Lenox, Berkshires 01240
    5 of 5 bubbles Reviewed 5 days ago
    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...
    5 of 5 bubbles Reviewed January 19, 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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    1 / 30
    Lenox
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Wi-Fi
    • Private Yard
    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- HAS A SOFA SLEEPER TO ACCOMMODATE 2 MORE GUESTS. KITCHENETTE W/ LG CEILING... View all property information
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    Lenox, Berkshires 01240
    1 / 12
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    • x
    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.... View all property information
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    Lenox, Berkshires 01240
    1 / 24
    Lenox
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • x
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    Lenox, Berkshires 01240
    1 / 16
    Lenox
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    Lenox, Berkshires 01240
    1 / 5
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    Lenox, Berkshires 01240
    1 / 17
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    Location Information
    Lenox, Berkshires 01240
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    1 / 22
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Lenox, Berkshires 01240
    1 / 24
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Lenox, Berkshires 01240
    1 / 23
    Lenox
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Lenox, Berkshires 01240
    1 / 21
    Lenox
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Patio
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    • x
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    Lenox, Berkshires 01240
    1 / 7
    Lenox
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • ?
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    Lenox, Berkshires 01240
    1 / 24
    Lenox
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    Lenox, Berkshires 01240
    1 / 22
    Lenox
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • x
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    Lenox, Berkshires 01240
    1 / 21
    Lenox
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • ?
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    Lenox, Berkshires 01240
    1 / 24
    Lenox
    5 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    • Balcony
    • Washer
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    • Patio
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    • x
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    Lenox, Berkshires 01240
    1 / 24
    Lenox
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Patio
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    Lenox, Berkshires 01240
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    1 / 19
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • x
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    Lenox, Berkshires 01240
    1 / 11
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Lenox, Berkshires 01240
    1 / 24
    Lenox
    10 Bedrooms, 10 Bathrooms, Sleeps 17 | Quick View
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    • Patio
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    • Shared Indoor Pool
    • Hot Tub
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    • x
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    Lenox, Berkshires 01240
    1 / 24
    Lenox
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • x
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    • x
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    Lenox, Berkshires 01240
    1 / 24
    Lenox
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Satellite TV
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
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    • x
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    Lenox, Berkshires 01240
    1 / 6
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
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    • ?
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    • x
    Location Information
    Lenox, Berkshires 01240
    1 / 15
    Lenox
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
    • Central Heating
    • Hot Tub
    • Washer
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    Location Information
    Lenox, Berkshires 01240
    1 / 24
    Lenox
    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Satellite TV
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    • Air Conditioning
    • Grill
    • Patio
    • DVD Player
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    Location Information
    Lenox, Berkshires 01240
    1 / 11
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Patio
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    Location Information
    Lenox, Berkshires 01240
    1 / 21
    Lenox
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Air Conditioning
    • Balcony
    • Parking
    • Satellite TV
    • Internet Access
    • Washer
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Lenox, Berkshires 01240
    1 / 24
    Lenox
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
    • Hot Tub
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    • Shared Indoor Pool
    • Washer
    • Patio
    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Lenox, Berkshires 01240
    1 / 24
    Lenox
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Sauna
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
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    • x
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    Lenox, Berkshires 01240
    1 / 19
    Lenox
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    Location Information
    Lenox, Berkshires 01240

    The following rentals are within 5 miles of Lenox, Massachusetts.

    1 / 16
    5 of 5 bubbles (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed July 31, 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...
    4 of 5 bubbles Reviewed October 24, 2013
    Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
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    1 / 25
    5 of 5 bubbles (1) Excellent
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Parking
    • Patio
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    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed November 28, 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 has...
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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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    • DVD Player
    • Washer
    • Private Yard
    • Satellite TV
    • Grill
    • Secure Parking
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Richmond, Berkshires 01254
    5 of 5 bubbles Reviewed June 14, 2016
    My wife and I stayed here for a week in June. The hosts/owners are new to the rental business, but were eager to make sure everything was in order for us. The house is very well...
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    1 / 30
    5 of 5 bubbles (1) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat. Welcome to ‘The Redway House’! You’ll... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed October 23, 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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    1 / 10
    4.5 of 5 bubbles (6) Very good
    Richmond
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Richmond, Berkshires 01254
    3 of 5 bubbles Reviewed October 26, 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...
    5 of 5 bubbles Reviewed September 7, 2015
    This house was very comfortable and quiet. We had everything that we needed in the house. The house was clean. The beds were comfortable and cozy. The neighborhood was also quiet...
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    1 / 20
    5 of 5 bubbles (26) 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
    • Child-friendly
    • Smoking allowed
    • x
    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
    4 of 5 bubbles Reviewed January 2, 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...
    5 of 5 bubbles Reviewed May 9, 2016
    Our group of eight adults had a very wonderful experience at Elaine's Berkshire farmhouse. We found it in excellent condition. Full kitchen had everything we needed to create...
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    1 / 21
    Stockbridge
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    Stockbridge, Berkshires 01262
    1 / 32
    5 of 5 bubbles (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
    • Child-friendly
    • x
    • Smoking allowed
    • 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 1 week ago
    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 November 9, 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 / 17
    5 of 5 bubbles (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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 January 4, 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 / 17
    5 of 5 bubbles (2) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    • Central Heating
    • Grill
    • Internet Access
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    • Mountain Views
    • Hot Tub
    • Outdoor Dining Area
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed October 11, 2015
    Rustic and vintage are apt descriptions of the house itself. It has stories to tell! And to matched its abundant, well aged charm is the friendly and generous host. Joanne made us...
    5 of 5 bubbles Reviewed June 12, 2014
    I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
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    1 / 22
    5 of 5 bubbles (3) Excellent
    Lee
    6 Bedrooms, 5 Bathrooms, Sleeps 26 | Quick View
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    • Private Yard
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    220 acres with tennis, yoga studio, gym 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... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed December 21, 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...
    5 of 5 bubbles Reviewed August 11, 2016
    The Playhouse is a magical place to connect with friends and family. There are a half dozen living spaces that offer anything from quiet reading areas with a view, to 40 person...
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    1 / 26
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Patio
    • Grill
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    • Satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Stockbridge, Berkshires 01238
    1 / 8
    5 of 5 bubbles (1) Excellent
    Lee
    Private Room, 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
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed June 17, 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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    1 / 4
    5 of 5 bubbles (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
    • ?
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    • x
    About this property
    first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed June 17, 2014
    And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
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    1 / 8
    5 of 5 bubbles (2) Excellent
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • Air Conditioning
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 bubbles Reviewed December 18, 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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    1 / 10
    5 of 5 bubbles (1) 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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 bubbles Reviewed October 18, 2016
    We had a wonderful time staying at this property. The house is full of charming details - we kept discovering art objects till the time of our departure. The kids had fun using...
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    1 / 20
    5 of 5 bubbles (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
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 bubbles Reviewed August 27, 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...
    5 of 5 bubbles Reviewed November 2, 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 her...
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