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Great Barrington Rentals

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68 Houses

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$261

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

$273

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

$343

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$171

Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!

Great Barrington tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$103

Great rentals within 20 miles that match your search

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

$370

Hillhouse Log Cabin

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 13

“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfect place to recharge.

Price per night from

$484

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$512

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

Responds fast! avg. 47 minutes

Price per night from

$296

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 42 minutes

Price per night from

$854

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$205

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

$228

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$854

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$204

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,138

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$813

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$152

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$325

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$171

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$171

Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$569

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 44 minutes

Price per night from

$285

Lake House

Lakeville house

5 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 50 minutes

Price per night from

$683

The Barn at Copake Lake

Craryville barn

3 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$682

My Country Home

Craryville house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$171

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 0 minutes

Price per night from

$163

Babbling Brook Retreat

Lakeville apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$262

Chalet near 4 ski resorts with hot tub

East Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,023

Ski Retreat -- Private Modern on 40 Acres of Land

Ashley Falls house

4 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$909

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$279

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$199

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby areas and we had a great time spending nights by the wood stove watching movies on their entertainment setup. I'd definitely recommend it for anyone looking to get out of the city for a few days to just relax and do something different!

Price per night from

$170

Modern Glass House

Taghkanic house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$512

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 40 minutes

Price per night from

$571

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 39 minutes

Price per night from

$229

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$286

The Heart of Berkshires

Lee house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$400

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$314

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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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