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Responds fast! avg. 1 hour 10 minutes
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$565
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$202
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.
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$367
“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.
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$294
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$311
Responds fast! avg. 1 hour 42 minutes
Price per night from
$847
Price per night from
$170
Beautifully decorated & immaculate log chalet
Hillsdale log cabin
3 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 1 hour 25 minutes
Price per night from
$226
Charming 2+2 Lakeside Cottage on Best Lake in CT
Salisbury cottage
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$203
“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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$226
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$847
Total Privacy! Tanglewood Retreat With Berkshire Views!
Hillsdale house
5 bedrooms / 5 bathrooms / sleeps 14
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$1,129
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$150
Newly Renovated Colonial on the River! Sleeps 5-6
Stockbridge house
3 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$322
Responds fast! avg. 3 hours 0 minutes
Price per night from
$162
Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh
Stockbridge house
3 bedrooms / 5 bathrooms / sleeps 8
Price per night from
$897
Tentrr Signature Site - Great Barrington Campsite - With Pool!
Great Barrington tented camp
1 bedroom / 1 bathroom / sleeps 4
Responds fast! avg. 1 hour 45 minutes
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$102
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$277
“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!
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$169
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$282
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$565
“Relaxation Overload” Went with the girlfriend for a weekend getaway and chose the perfect place. Extremely relaxing and soothing trip. Everything you need is there, french press? Yep. Towels? Yep. Amazing art? Yep! This place is incredibly decorated and if you forgot anything there is a 99% chance there is an extra in the house. When we arrived everything was set up perfectly and the fire place even had a "Light Here" sign. I highly recommend this place and Danielle was amazing to work with. Every question was answered and she was very polite. This is a need to visit place!
Responds fast! avg. 3 hours 54 minutes
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$271
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$516
Enjoy horses and the largest recreational lake in Massachusetts
East Otis apartment
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$126
“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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$487
Lakefront Berkshires Ski/Summer House, Great Views
Great Barrington house
4 bedrooms / 2 bathrooms / sleeps 10
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$263
New Timberframe House Rental in the Berkshire Mountains, Masschusetts
Hinsdale house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$218
Tentrr Signature Site - Berkshire Mountain Hideaway
Richmond tented camp
1 bedroom / 1 bathroom / sleeps 4
Responds fast! avg. 1 hour 44 minutes
Price per night from
$136
Tentrr State Park Site - NY Taconic State Park: High Valley Rd Site E
Copake Falls tented camp
1 bedroom / 1 bathroom / sleeps 6
Responds fast! avg. 1 hour 44 minutes
Price per night from
$155
Tentrr State Park Site - NY Taconic State Park: Orphan Rd Site C
Copake Falls tented camp
1 bedroom / 1 bathroom / sleeps 6
Responds fast! avg. 1 hour 44 minutes
Price per night from
$155
Responds fast! avg. 1 hour 44 minutes
Price per night from
$115
Tentrr State Park Site - NY Taconic State Park: Orphan Rd Site B
Copake Falls tented camp
1 bedroom / 1 bathroom / sleeps 4
Responds fast! avg. 1 hour 44 minutes
Price per night from
$155