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

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Check prices for these dates

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

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 AED 774
AED 1,200 total
includes taxes & fees
13 Jul - 14 Jul
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, (48 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
The price is AED 6,108
AED 9,129 total
includes taxes & fees
2 Aug - 3 Aug
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 AED 2,079
AED 4,878 total
includes taxes & fees
13 Jul - 14 Jul
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
9.8 out of 10, Exceptional, (33 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 AED 955
AED 1,449 total
includes taxes & fees
19 Jul - 20 Jul
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 AED 397
AED 744 total
includes taxes & fees
13 Jul - 14 Jul
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 AED 331
AED 1,231 total
includes taxes & fees
16 Jul - 17 Jul
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 AED 390
AED 519 total
includes taxes & fees
12 Jul - 13 Jul
All the comforts of home
TV

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is AED 582
AED 1,918 total
includes taxes & fees
12 Jul - 13 Jul
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 AED 1,293
AED 2,596 total
includes taxes & fees
12 Jul - 13 Jul
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 AED 698
AED 1,308 total
includes taxes & fees
15 Jul - 16 Jul
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 AED 882
AED 1,403 total
includes taxes & fees
16 Jul - 17 Jul
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
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 AED 1,212
AED 3,159 total
includes taxes & fees
21 Jul - 22 Jul
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 AED 870
AED 1,842 total
includes taxes & fees
12 Jul - 13 Jul
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 AED 1,113
AED 2,158 total
includes taxes & fees
4 Aug - 5 Aug
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 AED 777
AED 1,684 total
includes taxes & fees
13 Jul - 14 Jul
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 AED 1,348
AED 2,516 total
includes taxes & fees
13 Jul - 14 Jul
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 AED 711
AED 1,602 total
includes taxes & fees
13 Jul - 14 Jul
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 AED 2,384
AED 4,025 total
includes taxes & fees
19 Jul - 20 Jul
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 AED 845
AED 1,395 total
includes taxes & fees
12 Jul - 13 Jul
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

8/10 Good
"The hotel is a few minutes from Tanglewood and the Berkshire hotspots. Super friendly staff. Very accommodating. The place is a bit dated, but that has a retro charm like places on the Cape. The grounds are lovely. The breakfast is like other hotel breakfast. Lots of options: cereal, oatmeal, eggs, sausage, hard boiled eggs, fruit, bread, pastries, etc. My only complaint was the bed, which had a mattress in desperate need of replacement. We referred to it as sleeping in the valley because it made us roll to the center. It was also really high, which was challenging in an accessible room. I called and they had a stool for me within 5 minutes so we made it work. The people were so nice so I hate adding a complaint in my review. We would have asked for a room change but were there over a holiday weekend and I was pretty sure there wouldn’t be another option. The pluses outweigh the negatives so we had a good time."
Jean 3-night trip
Posted less than an hour ago
The Yankee Inn

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