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Price per night from
$818
“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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$373
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$744
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$659
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$402
Great rentals within 20 miles that match your search
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$261
Charming, modernized 1810 Farmhouse perfectly located in Hillsdale, NY
Hillsdale house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$345
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$115
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$569
Holiday Inn Club Vacations Oak N' Spruce 2br suite Friday check-ins
South Lee condo
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$70
Beautiful, Special 5 Star Estate! Perfect for Family/Friend Reunions & Retreats!
Old Chatham villa
- 9 bedrooms
- 5 bathrooms
- sleeps 16
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$1,264
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$156
Holiday Inn Club Vacations Oak N' Spruce 2BR Suite SATURDAY Check-Ins
South Lee condo
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$70
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$173
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$918
6BR Berkshire Bliss - 38 private acres - close to skiing and town
Lanesborough house
- 6 bedrooms
- 5 bathrooms
- sleeps 15
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$798
Enjoy horses and the largest recreational lake in Massachusetts
East Otis apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
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$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
“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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$298
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$172
Responds fast! avg. 3 hours 14 minutes
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$229
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
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$218
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$686
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$573
Responds fast! avg. 1 hour 12 minutes
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$344
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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$172
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$196
Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!
Hancock studio
- Studio
- 1 bathroom
- sleeps 4
Responds fast! avg. 1 hour 45 minutes
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$122
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$458
Private Home Overlooking Stevens Lake (31 Night Min)
Great Barrington house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$572
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$343