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95 Houses
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
$805
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$339
Price per night from
$928
Family-friendly Cottage Near Lake, Tanglewood
Stockbridge cottage
3 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$328
Responds fast! avg. 2 hours 34 minutes
Price per night from
$629
Newly Renovated Colonial on the River! Sleeps 5-6
Stockbridge house
3 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$323
Great rentals within 20 miles that match your search
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$788
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$301
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$236
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$829
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$175
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$1,315
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
$237
Total Privacy! Tanglewood Retreat With Berkshire Views!
Hillsdale house
5 bedrooms / 5 bathrooms / sleeps 14
Price per night from
$1,250
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$184
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$208
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$264
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$161
7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside
Hancock condo
2 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$248
Responds fast! avg. 1 hour 16 minutes
Price per night from
$612
Lake House w/ Deck & Views, Mins to Jiminy Peak!
Lanesboro cottage
3 bedrooms / 2 bathrooms / sleeps 10
Responds fast! avg. 1 hour 49 minutes
Price per night from
$444
Responds fast! avg. 2 hours 22 minutes
Price per night from
$449
Berkshire Blueberry Lodge LLC - Near Jiminy Peak
Stephentown lodge
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$438
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$152
Responds fast! avg. 39 minutes
Price per night from
$263
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$579
“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
$220
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$858
Responds fast! avg. 2 hours 22 minutes
Price per night from
$518
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$318
Responds fast! avg. 3 hours 28 minutes
Price per night from
$169
Price per night from
$525
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
$268
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