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Price: high to low
Number of reviews
Price per night from
$856
One of the Finest Homes and Best location in the Berkshires
Stockbridge house
4 bedrooms / 3 bathrooms / sleeps 10
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$802
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$629
Newly Renovated Colonial on the River! Sleeps 5-6
Stockbridge house
3 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$325
Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh
Stockbridge house
3 bedrooms / 5 bathrooms / sleeps 8
Price per night from
$911
Great rentals within 20 miles that match your search
Berkshires Spacious Comfortable Charming Farmhouse
Lee apartment
3 bedrooms / 2 bathrooms / sleeps 8
“lovely stay” 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 night.
Price per night from
$371
“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfect place to recharge.
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$485
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$514
“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.
Responds fast! avg. 21 minutes
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$297
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$314
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$428
Responds fast! avg. 1 hour 42 minutes
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$856
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$171
Beautifully decorated & immaculate log chalet
Hillsdale log cabin
3 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 1 hour 39 minutes
Price per night from
$228
“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby areas and we had a great time spending nights by the wood stove watching movies on their entertainment setup. I'd definitely recommend it for anyone looking to get out of the city for a few days to just relax and do something different!
Price per night from
$170
Charming 2+2 Lakeside Cottage on Best Lake in CT
Salisbury cottage
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$206
“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.
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$228
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$719
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$205
Total Privacy! Tanglewood Retreat With Berkshire Views!
Hillsdale house
5 bedrooms / 5 bathrooms / sleeps 14
Price per night from
$1,141
Responds fast! avg. 3 hours 28 minutes
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$257
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$152
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$262
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$571
Responds fast! avg. 1 hour 10 minutes
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$571
Responds fast! avg. 3 hours 17 minutes
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$285
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$683
Responds fast! avg. 3 hours 0 minutes
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$163
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$1,026
Price per night from
$280
Lakefront Berkshires Ski/Summer House, Great Views
Great Barrington house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$262
New Timberframe House Rental in the Berkshire Mountains, Masschusetts
Hinsdale house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$217
Tentrr Signature Site - Great Barrington Campsite - With Pool!
Great Barrington tented camp
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$103