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126 Houses
Lakefront Berkshires Ski/Summer House, Great Views
Great Barrington house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$220
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
$267
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
$356
Cozy and clean in Gt Barrington- available for October
Great Barrington house
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$178
Private Berkshire Estate w/Pool & Tennis Court
Great Barrington house
4 bedrooms / 4 bathrooms / sleeps 12
Price per night from
$675
NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr
Great Barrington house
4 bedrooms / 4 bathrooms / sleeps 8
Price per night from
$572
Price per night from
$516
Turning Point - Family Retreat & Group Getaway
Great Barrington house
7 bedrooms / 8 bathrooms / sleeps 15
Price per night from
$948
Great rentals within 20 miles that match your search
Price per night from
$534
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$593
Price per night from
$2,359
Luxury Fox Hollow Estate Home on Laurel Lake, Hot Tub, Dock with Kayak, Canoe++
Lenox house
5 bedrooms / 3 bathrooms / sleeps 14
Price per night from
$702
Responds fast! avg. 1 hour 1 minutes
Price per night from
$466
Riverwood - Cozy Carriage House in the Woods
Falls Village apartment
1 bedroom / 1 bathroom / sleeps 2
Price per night from
$266
The perfect Southern Berkshire winter vacation esc
Sheffield house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$592
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
$355
Price per night from
$201
Picturesque 19th century home on 3 private acres
New Marlborough house
4 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$178
Price per night from
$473
Price per night from
$249
Price per night from
$710
4 Bedroom Furnished House in Lakeville Connecticut
Lakeville house
4 bedrooms / 3 bathrooms / sleeps 8
Price per night from
$385
Responds fast! avg. 3 hours 4 minutes
Price per night from
$326
Price per night from
$379
Price per night from
$379
Price per night from
$506
Price per night from
$379
Charming Private Guest Suite in Historic Village in the Berkshires
New Marlborough studio
Studio / 1 bathroom / sleeps 2
Price per night from
$113
“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
$237
Price per night from
$212
Newly Renovated Colonial on the River! Sleeps 5-6
Stockbridge house
3 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$338
Walk To Tanglewood, Stocbridge Bowl, Wheatleigh, HTD Pool, Hot Tub, Luxury Home
Lenox house
5 bedrooms / 5 bathrooms / sleeps 15
Price per night from
$1,179
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