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Great Barrington Rentals

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126 Houses

Shaker Hill

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$445

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

Private Home Overlooking Stevens Lake

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 6

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

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$534

Luxury Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$593

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$177

Evergreen Pines Country Estate Villa

Ancram house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$2,359

Price per night from

$702

Charming Farmhouse on Magical 4 Acre Estate

Tyringham villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 1 minutes

Price per night from

$466

My Country Home

Craryville house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$178

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

Berkshire Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

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

Country Retreat w/ Pool Near Hip Hudson, NY

Hudson house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$473

Berkshires on the Pond

Becket house

2 bedrooms / 2 bathrooms / sleeps 2

Price per night from

$148

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$249

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$710

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$207

4 Bedroom Furnished House in Lakeville Connecticut

Lakeville house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$385

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 4 minutes

Price per night from

$326

2 Bedroom Hudson Valley Farm House

Craryville guest house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$379

1 Bedroom Hudson Valley Farm House

Craryville guest house

1 bedroom / 3 bathrooms / sleeps 2

Price per night from

$379

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$506

4 Bedroom Hudson Valley Farm House

Craryville guest house

4 bedrooms / 3 bathrooms / sleeps 8

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

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

“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

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$119

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

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

Price per night from

$1,179

Viewing 38 of 126
rentals in Great Barrington

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Top Destination reviews

Cozy and clean in Gt Barrington- available for October
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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