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Vacation Rentals in Sandisfield, MA and nearby

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    1 / 15
    5 of 5 stars (2) Excellent
    Sandisfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    The following rentals are within 25 kilometres of Sandisfield, Massachusetts.

    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    1 / 17
    5 of 5 stars (2) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Parking
    • Mountain Views
    • Hot Tub
    • Outdoor Dining Area
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • 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 stars Reviewed 11 October 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 stars Reviewed 12 June 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 / 10
    5 of 5 stars (2) Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Balcony
    • Parking
    • Grill
    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and... View all property information
    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed 24 July 2015
    New England working farm. Lovely setting Great hospitality. Easy access to Tanglewood and other Berkshire attractions.
    5 of 5 stars Reviewed 22 July 2015
    What a beautifully decorated and comfortable cottage! Incredible deck for long lazy summer afternoons. Property owners were wonderful ... friendly & helpful. Cannot wait to...
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    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    see better & more photos of property here (copy-paste-edit in browser): tinyurl DOT com/hoqrp7n 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... View all property information
    Location Information
    Lee, Berkshires 01238
    1 / 16
    5 of 5 stars (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
    • Porch
    • Parking
    • Washer
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
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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... View all property information
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    Stockbridge, Berkshires 01262
    5 of 5 stars 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...
    4 of 5 stars Reviewed 24 October 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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    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
    • Terrace
    • Satellite TV
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    • Parking
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
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    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest... View all property information
    Location Information
    Tyringham, Berkshires 01264
    1 / 13
    5 of 5 stars (2) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Outdoor Dining Area
    • Air Conditioning
    • Satellite TV
    • Parking
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
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    About this property
    Welcome to our family getaway in the Berkshires which we also rent out. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short walk to the Norman Rockwell Museum, Chesterwood House, and Botanical Gardens. The sunny 1st floor features a living room... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 26 May 2015
    This home is beautiful! It is an older home, and comes with the charm and quirks, which make it even more lovely! The décor is modern, simple and fits the house wonderfully. The...
    5 of 5 stars Reviewed 22 January 2015
    This home has everything. It also happens to be a wonderfully furnished home. The home owner left little treats for us as we arrived late the first night. The surrounding...
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    Otis
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • x
    About this property
    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY... View all property information
    Location Information
    Otis, Berkshires 01255
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    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Elder access
    • x
    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the... View all property information
    Location Information
    Monterey, Berkshires 01245
    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
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 4 . nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full... View all property information
    Location Information
    Lee, Berkshires 01238
    Great Barrington
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Mountain Views
    • Satellite TV
    • Grill
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Great Barrington
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Waterfront
    • Satellite TV
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    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Welcome to my dream come true! Pick from your own orchards, vegetable gardens and perennial beds. Swim in your own Green River or your beautiful heated swimming pool. And of course, SKI, SKI, SKI!! This home is beautiful four seasons of the year. Major highlights include a fireplace in the kitchen... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 16
    4.5 of 5 stars (3) Very good
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Wi-Fi
    • Shared Garden
    • Patio
    • Air Conditioning
    • Outdoor Dining Area
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    One bedroom air conditioned apartment with private entrance in 18th century house in Historic District of Stockbridge. Wonderful views of the river, 18th green of Stockbridge Golf Club and the Berkshire Hills. 5 minutes walk to the famous Red Lion Inn/town center.Self contained and private. You... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 13 July 2015
    I just got back from my weekend stay here last night, and if I hadn't been so tired, I would have posted this review already! I was absolutely thrilled with this rental - where...
    4 of 5 stars Reviewed 21 June 2015
    Lovely home, great location, walking distance to the town of Stockbridge. Many things to see and do while we stayed for our five day trip. Must see: Naumkeg, Shrine of Divine...
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    1 / 4
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • ?
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    • x
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    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 stars Reviewed 17 June 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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    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
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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!... View all property information
    Location Information
    Lee, Berkshires 01238
    1 / 12
    1 of 5 stars (1) Terrible
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or... View all property information
    Location Information
    Great Barrington, Berkshires 01236
    1 / 19
    5 of 5 stars (1) Excellent
    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Porch
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
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    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • ?
    • x
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    • x
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    About this property
    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are... View all property information
    Location Information
    Tyringham, Berkshires 01264
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    1 / 11
    Becket
    6 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Grill
    • Porch
    • Patio
    • Internet Access
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    • Central Heating
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
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    About this property
    Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds.... View all property information
    Location Information
    Becket, Berkshires 01223
    1 / 32
    5 of 5 stars (2) Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed 18 August 2015
    Amazing place for its location, layout, and superb owner! 1. The location is ideal. It's under 3 miles to Jacobs Pillow Dance, about 25 minutes to Tanglewood, 12 minutes form...
    5 of 5 stars Reviewed 29 August 2014
    This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
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    Tyringham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Washer
    • Mountain Views
    • Central Heating
    • Balcony
    • Wi-Fi
    • DVD Player
    • Porch
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
    About this property
    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English... View all property information
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    Tyringham, Berkshires 01264
    1 / 16
    Becket
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Internet Access
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    About this property
    Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional... View all property information
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    Becket, Berkshires 01223
    1 / 12
    5 of 5 stars (3) Excellent
    Alford
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
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    • Pet-friendly
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    About this property
    The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural... View all property information
    Location Information
    Alford, Massachusetts 01266
    5 of 5 stars Reviewed 2 May 2013
    The Smith Homestead is a fantastic get-away for those looking to get peace and quiet in the picturesque Berkshire community of alford. The drive up to alford was both easy and...
    5 of 5 stars Reviewed 10 April 2013
    Set back in the Berkshires, Alford Ma is a stone's throw from New York State. The small town borders Great Barrington, which is rich in activity. Many famous americans have...
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    1 / 11
    4 of 5 stars (2) Very good
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • x
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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... View all property information
    Location Information
    Lee, Berkshires 01238
    4 of 5 stars Reviewed 17 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 the...
    4 of 5 stars Reviewed 24 September 2010
    The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at...
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    1 / 48
    Lee
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Balcony
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    • Central Heating
    • Waterfront
    • Internet Access
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
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    About this property
    Chanterwood is an expansive, light-filled modern home with the luxuries one expects today in a lakefront estate blended with the comfort, casualness and intimacy of its' 100-year old Inn heritage. Chanterwood is newly available for summer 2016 - illness forced tenants to cancel summer plans... View all property information
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    Lee, Berkshires 01238
    1 / 13
    5 of 5 stars (8) Excellent
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    • DVD Player
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Elder access
    • x
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    About this property
    Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful,... View all property information
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed 3 November 2014
    This was exactly what we were looking for in a getaway rental! The place was exactly as described and every bit of the transaction went by without a hitch. The house was cozy...
    5 of 5 stars Reviewed 28 June 2014
    The Becket cabin is a great getaway for young families. Our 4- and 2-year-old happily played about in and around the cabin and we spent a lot of time building fires in the fire...
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    1 / 11
    3.5 of 5 stars (3) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 stars Reviewed 14 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...
    3 of 5 stars Reviewed 4 July 2015
    On the water with canoes, close to Tanglewood, but tired amenities. Poor second bedroom, not yet cleaned until after we arrived, but most unfortunate it was a very hot weekend...
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    Monterey
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent... View all property information
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    Monterey, Berkshires 01245
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 1 | Quick View
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    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... View all property information
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    Lee, Berkshires 01238
    1 / 14
    5 of 5 stars (1) Excellent
    Sheffield
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    This beautiful and secluded winter utopia is perfect for your Berkshire winter vacation getaway. Private and secluded, this home is nestled on five private acres in the woods located conveniently within fifteen minutes to many area attractions. Wether you are looking to ski the slopes, capture the... View all property information
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    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed 28 October 2015
    Beautifully decorated house nestled in the Berkshires. A true getaway. Plenty of room for a family with the latest TV/computer set up. Big kitchen with the best appliances...
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    1 / 18
    5 of 5 stars (2) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    • Sauna
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    • x
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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 had 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... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars Reviewed 29 October 2015
    The Lake House was paradise. It is situated right in The Berkshires on Rte. 20 with easy access to everything. We golfed, canoed, played tennis, swam, hiked, went to museums...
    5 of 5 stars Reviewed 27 October 2015
    We were a group of 8 friends who have vacationed together annually. This was by far the best appointed house we have rented in 30 years. The owners, Margie and Frank were...
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    5 of 5 stars (19) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows..... View all property information
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    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed 25 October 2015
    My husband and I stayed at this very charming cottage for 3 nights in the beginning of October and we very much enjoyed our stay. The furniture and decor were very french...
    5 of 5 stars Reviewed 27 August 2015
    I stayed in the cottage with my girlfriend and our small dog and we had a fantastic time! The cottage had everything we needed (wifi, large bathroom, dining table, cable TV) and...
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    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • x
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    About this property
    Beautifully appointed farm house situated on 200 acres of this pristine estate located in the heart of the Berkshires. This home offers three bedrooms, three bathrooms, fully equipped kitchen, laundry room, deck and porch. Perfectly located to all The Berkshires attractions, This home is within 4... View all property information
    Location Information
    Stockbridge, Berkshires
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Vacation home centrally located in the Berkshires, 1 mile from Norman Rockwell and 3 miles from Tanglewood, on a quiet country road. Spacious grounds with large 2-level deck overlooking gardens and woods, private in-ground pool with pool house and deck, hot tub. House includes 3 bedrooms, 2 newly... View all property information
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    Stockbridge, Berkshires 01262
    1 / 10
    4 of 5 stars (1) Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Outdoor Dining Area
    • DVD Player
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    • x
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    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking... View all property information
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    Great Barrington, Berkshires 01230
    4 of 5 stars Reviewed 2 February 2015
    My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the...
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    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Our 1762 Farmhouse is lovingly being restored with gardens in the Berkshires. Mission statement: Educating members in life, farming, and creative art skills acknowledging God as our provider. One mile from the Norman Rockwell Museum and 5 miles from Tanglewood. Come join the farm 'Agritourism'... View all property information
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    Stockbridge, Berkshires 01262
    South Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample... View all property information
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    South Lee, Berkshires 01260
    1 / 13
    4.5 of 5 stars (16) Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
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    • Mountain Views
    • Hot Tub
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) **... View all property information
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    Monterey, Berkshires 01245 0933
    5 of 5 stars Reviewed 18 November 2015
    I took my wife and three young children up to this house for columbus day week. We had a blast. The house has a real cabin in the woods feel and is just a short walk to the...
    4 of 5 stars Reviewed 9 November 2015
    When looking for a house to rent in the Berkshires I began with spots in the towns. However we chose this place due to the reasonable price. As it turned out we liked the remote...
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    the garden room is a small room with a full sized bed. everything is floral, even the closet walls. it 's a sweet room with even a wood stove. it has an entrance to the courtyard just outside in the hall, the bath may be shared depending on the situation. bath has shower and lovely old sink. bath... View all property information
    Location Information
    Lee, Berkshires 01238
    South Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Shared Indoor Pool
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    • Pet-friendly
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    • x
    About this property
    Close to ski resorts, cross country skiing, restaurants, and all the cultural offerings of the Berkshires. The Berkshire region is a year-round destination for vacationers, so the Oak N’ Spruce Resort offers guests a selection of amenities to keep them coming back no matter what season. The... View all property information
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    South Lee, Berkshires 01260
    Tyringham
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
    • x
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    About this property
    This turn of the century cottage is located on a 130 acre property, and is stocked with linens. Three and a half baths, three full bedrooms, kitchen, living room, dining room, screened porches, a deck, and washer dryer. The house is across the brook and up a stone staircase (30 steps) from the... View all property information
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    Tyringham, Berkshires 01264
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 2 | Quick View
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    • Waterfront
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    • Private Garden
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    • Pet-friendly
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    • x
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    About this property
    Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water... View all property information
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    Becket, Berkshires 01223
    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Skiing: Property Is...
    • Patio
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    • Mountain Views
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    • Pet-friendly
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    • x
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    • x
    About this property
    This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The... View all property information
    Location Information
    Monterey, Berkshires 01245
    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
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    • x
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    • x
    About this property
    A bright, lovely and comfortable room with queen bed in a charming country farmhouse with adjoining private bath. Located in Tyringham, a bucolic, rural village on a scenic country road the beautiful and magical 'Hop Brook' valley. The house is surrounded by farmland surrounding it on all sides. A... View all property information
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    Tyringham, Berkshires 01264
    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Mountain Views
    • Waterfront
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    • Pet-friendly
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    • x
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    About this property
    A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A... View all property information
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    Stockbridge, Berkshires 01260
    5 of 5 stars Reviewed 18 May 2010
    This house had it all... my wife and I loved our time there. During the day we would either sit on the deck and read or go swimming in our own private lake that was very, very...
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    1 / 19
    4.5 of 5 stars (28) Very good
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Grill
    • Mountain Views
    • Patio
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    • Secure Parking
    • Internet Access
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
    About this property
    The Cottage, in picturesque Stockbridge, has the PERFECT location -- minutes from Main Street Lenox, Main Street Stockbridge, The Norman Rockwell Museum, Berkshire Botanical Gardens, Tanglewood Music Festival, The Shrine of the Divine Mercy at the Congregation of Marians, shops, theaters, hiking... View all property information
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    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 7 November 2015
    The house was beautiful. We stayed with two of our children--a young man and a teenager. There was plenty of room for all of us. The breakfast was wonderful. The immediate...
    4 of 5 stars Reviewed 13 August 2015
      Want to feel like you have been invited to stay with an old - or new - friend in a special part of the Berkshires, then this is the place for you. Only 4 mi...
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    Becket
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
    • Terrace
    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    Large home in wooded area of the Berkshires. Ideal for all the summer events such as visiting Great Barrington, Lenox, Lee, Stockbridge. Many mountain areas for picnics, biking, hiking in the summer and winter events such as skiing and snowboarding. Near Center pond where there are many boating... View all property information
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    Becket, Berkshires 01223
    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Grill
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    • Shared Garden
    • Outdoor Dining Area
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,... View all property information
    Location Information
    Great Barrington, Berkshires 01236