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91 Houses
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.
Price per night from
$264
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
Price per night from
$182
Private Berkshire Estate w/Pool & Tennis Court
Great Barrington house
4 bedrooms / 4 bathrooms / sleeps 12
Responds fast! avg. 1 hour 5 minutes
Price per night from
$659
NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr
Great Barrington house
4 bedrooms / 4 bathrooms / sleeps 8
Responds fast! avg. 2 hours 34 minutes
Price per night from
$572
Responds fast! avg. 2 hours 34 minutes
Price per night from
$516
NEW! Cozy Great Barrington Home 1 Mi to Ski Resort
Great Barrington house
4 bedrooms / 2 bathrooms / sleeps 9
Responds fast! avg. 14 minutes
Price per night from
$289
Great rentals within 20 miles that match your search
Price per night from
$2,586
Riverwood - Cozy Carriage House in the Woods
Falls Village apartment
1 bedroom / 1 bathroom / sleeps 2
Price per night from
$292
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$778
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$233
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$299
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$173
Price per night from
$1,299
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
$234
Total Privacy! Tanglewood Retreat With Berkshire Views!
Hillsdale house
5 bedrooms / 5 bathrooms / sleeps 14
Price per night from
$1,235
Price per night from
$206
Price per night from
$261
Price per night from
$159
Price per night from
$916
Responds fast! avg. 1 hour 16 minutes
Price per night from
$605
Responds fast! avg. 2 hours 22 minutes
Price per night from
$444
Price per night from
$174
Responds fast! avg. 2 hours 35 minutes
Price per night from
$290
Price per night from
$686
Price per night from
$572
“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
$217
Price per night from
$847
Newly Renovated Colonial on the River! Sleeps 5-6
Stockbridge house
3 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$319
Responds fast! avg. 2 hours 22 minutes
Price per night from
$511
Price per night from
$314
Responds fast! avg. 3 hours 28 minutes
Price per night from
$167
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