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83 Houses
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Monterey cottage
1 bedroom / 1 bathroom / sleeps 4
Responds fast! avg. 2 hours 44 minutes
Price per night from
$131
Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn
Monterey cottage
2 bedrooms / 1 bathroom / sleeps 2
Responds fast! avg. 2 hours 12 minutes
Price per night from
$241
Price per night from
$568
Responds fast! avg. 2 hours 22 minutes
Price per night from
$508
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$231
Responds fast! avg. 12 minutes
Price per night from
$237
Cozy Monterey Home w/ Porch: Walk to Lake Garfield
Monterey house
3 bedrooms / 3 bathrooms / sleeps 6
Responds fast! avg. 12 minutes
Price per night from
$242
Great rentals within 20 miles that match your search
Riverwood - Cozy Carriage House in the Woods
Falls Village apartment
1 bedroom / 1 bathroom / sleeps 2
Price per night from
$290
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$773
Price per night from
$172
Charming 2+2 Lakeside Cottage on Best Lake in CT
Salisbury cottage
2 bedrooms / 2 bathrooms / sleeps 4
Responds fast! avg. 50 minutes
Price per night from
$233
Total Privacy! Tanglewood Retreat With Berkshire Views!
Hillsdale house
5 bedrooms / 5 bathrooms / sleeps 14
Price per night from
$1,227
Price per night from
$181
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.
Price per night from
$284
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$259
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$158
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$911
Responds fast! avg. 2 hours 22 minutes
Price per night from
$441
Responds fast! avg. 2 hours 35 minutes
Price per night from
$288
“Home Away from Home ~ A great place to gather11” Had family coming from New York, Massachusetts and Connecticut to celebrate my birthday ~ hotels, motels are expensive, and they're not home. This house offered a great place to convene ~ outdoor gas grill, eating on the deck, well stocked kitchen and cozy living room. Spacious, comfortable with a lovely master bedroom with private bath. All bedrooms are located somewhat away from the living room which is nice. Walked to the lake with paddles and canoed with my son; got great coffee at the nearby General Store. Michael is wonderful to rent from and very accommodating.
Responds fast! avg. 6 minutes
Price per night from
$216
Price per night from
$841
Newly Renovated Colonial on the River! Sleeps 5-6
Stockbridge house
3 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$317
“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.
Price per night from
$227
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$312
Responds fast! avg. 3 hours 28 minutes
Price per night from
$165
“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.
Price per night from
$297
Cozy & Modern Home -mins from Tanglewood & Kripalu
West Stockbridge apartment
2 bedrooms / 1 bathroom / sleeps 6
Responds fast! avg. 2 hours 34 minutes
Price per night from
$115
New Timberframe House Rental in the Berkshire Mountains, Masschusetts
Hinsdale house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$217
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
$343
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$515
Beautifully decorated & immaculate log chalet
Hillsdale log cabin
3 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 9 minutes
Price per night from
$229
Price per night from
$156
Tentrr Signature Site - Tamarack at Running Fox Berry Farm
Chesterfield tented camp
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$149
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