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Great Barrington Rentals

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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

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

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

Private Home Overlooking Stevens Lake

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 6

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

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$194

Evergreen Pines Country Estate Villa

Ancram house

4 bedrooms / 4 bathrooms / sleeps 8

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

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$778

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$130

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$233

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$927

Babbling Brook Retreat

Lakeville apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$299

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$195

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$173

Country estate on 100 acres perfect for families

Chatham house

4 bedrooms / 4 bathrooms / sleeps 6

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

Bellavista Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$206

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$261

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$159

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$214

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$916

Chalet near 4 ski resorts with hot tub

East Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$605

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 22 minutes

Price per night from

$444

My Country Home

Craryville house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 14 minutes

Price per night from

$174

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 35 minutes

Price per night from

$290

Lake House

Lakeville house

5 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 46 minutes

Price per night from

$686

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$572

Outdoor getaway hunting,fishing,skiing..relaxation

Copake house

3 bedrooms / 2 bathrooms / sleeps 9

“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

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

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

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 22 minutes

Price per night from

$511

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$314

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 28 minutes

Price per night from

$167

Viewing 38 of 91
rentals in Great Barrington

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Top Destination reviews

Eco-friendly cozy home in Gt. Barrington
Easy, comfortable summer getaway!

My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the lake, the bedrooms were airy with cross ventilation and the screened in porch was a great place to linger over coffee in the morning. The location is also wonderful! It is only a 5 minute drive to lake Mansfield, 7or 8 minutes to downtown GB and a half our or less to Tanglewood. All in all we were very pleased with this quaint, little house.see more
Gem of the Berkshires, walk to downtown & lake.
Wonderful weekend in a wonderful home in Great Barrington

We are a group of 10 that gather from Mass./N.Y./ New Jersey every summer to enjoy all that the Berkshires have to offer. We came upon this gem and could not have been happier. The homeowners are a wonderful couple who take great pride in their home and this comes through in the way the place is appointed and artwork dispersed throughout the house.Yes, the house is a short walk to both town and the lake but truthfully sitting on the deck overlooking the mountains will keep you planted in one spot. Having your morning coffee overlooking the fog covered hills was a wonderful way to start your day.Neither the description nor the photos do this home justice, no question you will be pleased with your choicesee more
Berkshires: Romantic Cottage with spectacular view
the cottage description is a perfect fit "romantic getaway in id

We have stayed in many B&B;'s and cottage rentals on the east coast...this experience was one of the best! The owners are exceptional hosts and the accommodations are just as described...even better. The setting in the berkshires is fabulous and the location is a perfect location for touring the area (western ma and the Hudson valley). The hosts provide ample information about great restaurants and lovely walks/hikes in the area. We are already planning our next trip to the cottage!see more

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