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63 Houses
“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.
Responds fast! avg. 3 hours 58 minutes
Price per night from
$229
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$573
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$516
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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$373
“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.
Responds fast! avg. 47 minutes
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$298
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$315
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$430
Responds fast! avg. 1 hour 45 minutes
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$859
Price per night from
$172
Family-friendly Cottage Near Lake, Tanglewood
Stockbridge cottage
3 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$327
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$2,863
Beautifully decorated & immaculate log chalet
Hillsdale log cabin
3 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 1 hour 24 minutes
Price per night from
$229
“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
$171
Gem of the Berkshires, walk to downtown & lake.
Great Barrington house
5 bedrooms / 4 bathrooms / sleeps 12
“Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are beautiful. Thank you!
Price per night from
$344
Stunning New Construction All SeasonLakefront Home
Valatie house
3 bedrooms / 3 bathrooms / sleeps 5
“Fantastic House -- Lake, Poor” Yes, the house is wonderful. Beautiful views abound, it's well stocked with everything you'd want, and extremely clean. A five-star place. That said, the lake's dreadful, in our opinion. It's murky-black. We did go swimming in it, however, but it's so murky you can't see your thighs in the water, much less the bottom. Our twenty-something son wanted to swim across it, and I kept thinking, if he goes under you'd never see him. As it was, he did swim across and we followed in a row boat. We would definitely return were it not for the lake.
Price per night from
$279
Lakefront Berkshires Ski/Summer House, Great Views
Great Barrington house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$251
Berkshires: Romantic Cottage with spectacular view
Great Barrington cottage
1 bedroom / 1 bathroom / sleeps 3
“Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything looked just as in the pictures. The room is sunny, but stays nice and cool too (we were there in august). There is an overhead fan but we didn't even need it. The Sigels made us feel very much at home, but they also seemed to know that we were not looking for a chatty B&B; experience. There are plenty of little touches like a bottle of wine waiting for us, tea, sugar, and some other basics in the kitchenette. A hair dryer, eye shade in the bedside table, etc. But nothing seemed overly fussy-- they are naturally good hosts. The pool was absolutely perfect. Big enough to swim laps, but small enough to be a nice temperature. We spent one whole morning just floating in the pool. The view from the pool is stunning. I am sure there are some amazing hikes around (I had broken my tailbone so hiking will have to wait for next year). Great Barrington is a wonderful town too, so if you're wondering where to stay in the Berkshires, then you would be wise to choose GB. It's not huge, but we never really left town. The walkable part of town has great diners, a cool little coffee shop, a movie theatre, used book store, and great music and food at the Gypsy Joynt (a member of the family that owns it-- Jordan Weller-- put out the best CD I've heard in a long time!) On our last night there the Sigels suggested we go to the Guthrie Center for an open mic where we heard more great music. I can't say enough about the Seigel's cottage. We can't wait to go back next summer.
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$274
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$722
New Timberframe House Rental in the Berkshire Mountains, Masschusetts
Hinsdale house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$218
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$859
Price per night from
$205
Total Privacy! Tanglewood Retreat With Berkshire Views!
Hillsdale house
5 bedrooms / 5 bathrooms / sleeps 14
Price per night from
$1,145
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$687
Price per night from
$630
Responds fast! avg. 1 hour 3 minutes
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$258
Responds fast! avg. 3 hours 28 minutes
Price per night from
$516
One of the Finest Homes and Best location in the Berkshires
Stockbridge house
4 bedrooms / 3 bathrooms / sleeps 10
Responds fast! avg. 23 minutes
Price per night from
$802
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$144
Price per night from
$153
Newly Renovated Colonial on the River! Sleeps 5-6
Stockbridge house
3 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$327
Enjoy horses and the largest recreational lake in Massachusetts
East Otis apartment
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$126
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