A large stone church with a tall bell tower and arched windows.

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Great Barrington vacation homes

Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is ￥34,969
￥53,952 total
includes taxes & fees
Jul 13 - Jul 14
Cozy Riverside Berkshires Retreat
TV, fireplace, stereo

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (49 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
The price is ￥276,012
￥410,818 total
includes taxes & fees
Aug 2 - Aug 3
Great Barrington, Cabin Sleeps 14, Walk To Town
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (6 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥91,912
￥215,651 total
includes taxes & fees
Jul 13 - Jul 14
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is ￥43,837
￥66,376 total
includes taxes & fees
Jul 24 - Jul 25
Home in Great Barrington
2 bedrooms, free WiFi, bed sheets

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is ￥17,535
￥32,910 total
includes taxes & fees
Jul 13 - Jul 14
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ￥14,937
￥54,770 total
includes taxes & fees
Jul 16 - Jul 17
Real Estate: Therapy - Lake, Laundry, Love it
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (33 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥17,243
￥22,950 total
includes taxes & fees
Jul 12 - Jul 13
All the comforts of home
TV

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is ￥25,711
￥84,804 total
includes taxes & fees
Jul 12 - Jul 13
Charles Cottage Near Warren St New Renovation
Fridge, microwave, oven, stovetop

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
The price is ￥57,151
￥114,743 total
includes taxes & fees
Jul 12 - Jul 13
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (147 reviews)
"Great location"
United States
Will G.
The price is ￥30,848
￥57,834 total
includes taxes & fees
Jul 15 - Jul 16
Big farmhouse in the foothills of the Berkshires
Outdoor dining

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
The price is ￥38,966
￥62,008 total
includes taxes & fees
Jul 16 - Jul 17
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Private kitchen

Designer Home, Walk to Warren, Off-Street Parking, and 4-Bedroom/Loft

Designer Home, Walk to Warren, Off-Street Parking, and 4-Bedroom/Loft
Hudson
The price is ￥108,857
￥203,469 total
includes taxes & fees
Jul 28 - Jul 29
Designer Home, Walk to Warren, Off-Street Parking, and 4-Bedroom/Loft
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
The price is ￥60,187
￥149,225 total
includes taxes & fees
Jul 21 - Jul 22
NEW: Chic Modern Barn Style Home in Fun Area
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥38,479
￥81,428 total
includes taxes & fees
Jul 12 - Jul 13
Cheerful 3-bedroom cottage with woodstove
Property grounds

Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
The price is ￥62,022
￥111,873 total
includes taxes & fees
Aug 10 - Aug 11
Larkspire I Sleepy Hollow Lake I Beach & Firepit
Outdoor spa tub

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥33,755
￥73,793 total
includes taxes & fees
Jul 13 - Jul 14
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is ￥59,586
￥111,207 total
includes taxes & fees
Jul 13 - Jul 14
Treetop Hideaway in Tyringham
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥30,978
￥70,331 total
includes taxes & fees
Jul 13 - Jul 14
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is ￥105,372
￥177,910 total
includes taxes & fees
Jul 19 - Jul 20
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (9 reviews)
"Great experience! Only there for one night because our son had a wrestling tournament. Wish we would have had more time at property. "
United States
Rochelle F.
The price is ￥37,343
￥61,645 total
includes taxes & fees
Jul 12 - Jul 13
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Great Barrington Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Front desk staff was very accommodating. She was kind to let us check in as soon as rooms were cleaned. We traveled from California and were very sleepy and that made our stay more enjoyable."
MARIA THERESA 2-night trip
Posted 1 hour ago
The Yankee Inn

Find out more about Great Barrington

Great Barrington Vacation Homes information

Number of reviews
394
Accommodation
587 Vacation Homes
Lowest Price
￥22,950
Highest Price
￥410,818