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$682
Great rentals within 20 miles that match your search
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$327
Total Privacy! Tanglewood Retreat With Berkshire Views!
Hillsdale house
- 5 bedrooms
- 5 bathrooms
- sleeps 14
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$1,148
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$153
“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
“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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$299
Responds fast! avg. 3 hours 11 minutes
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$316
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$861
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$173
Responds fast! avg. 3 hours 45 minutes
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$230
“awesome beautiful place” I can't say enough about this. Place, perfect I guess Serene, peaceful,beautiful, quiet. Djuna the owner is Sweet and very efficient and provides every detail. The Whole are is perfect Oct a getaway, things to do places To shop,eat or just cuddle in with a fire. We will Definetly be returning as soon as we can.:)))
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$171
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$207
“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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$230
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$724
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$861
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$574
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$345
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$197
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$1,032
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$281
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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$229
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$287
Beautiful, Special 5 Star Estate! Perfect for Family/Friend Reunions & Retreats!
Old Chatham villa
- 9 bedrooms
- 5 bathrooms
- sleeps 16
Price per night from
$1,260
Lakefront Berkshires Ski/Summer House, Great Views
Great Barrington house
- 4 bedrooms
- 2 bathrooms
- sleeps 10
Price per night from
$251
“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
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$287
One of the Finest Homes and Best location in the Berkshires
Stockbridge house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Price per night from
$802
Berkshires: Romantic Cottage with spectacular view
Great Barrington cottage
- 1 bedroom
- 1 bathroom
- sleeps 3
“A Real Gem!!!” This cottage is the perfect place for two people. It is truly as beautiful as the pictures! The pool and grounds are exceptional and the view is breathtaking. The place is extremely well maintained and the owner is very kind and helpful. We had a fabulous weekend here and would gladly return!
Price per night from
$274