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Our top choices for Great Barrington vacation homes

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is ¥31,728
¥49,616 total
includes taxes & fees
May 13 - May 14
Cozy Riverside Berkshires Retreat

Modern Victorian Walk to Main Street

Modern Victorian Walk to Main Street
Great Barrington
10.0 out of 10, Exceptional, (27 reviews)
"The house and location both perfect for a girls weekend away! "
United States
karen b.
The price is ¥46,221
¥119,010 total
includes taxes & fees
May 12 - May 13
Modern Victorian Walk to Main Street

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, (4 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 ¥88,697
¥208,108 total
includes taxes & fees
May 18 - May 19
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ¥47,004
¥83,656 total
includes taxes & fees
May 12 - May 13
Cozy. Clean. Free bagel shop. 3 Fireplaces.

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is ¥16,639
¥22,146 total
includes taxes & fees
May 17 - May 18
All the comforts of home

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 ¥22,844
¥58,769 total
includes taxes & fees
May 12 - May 13
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is ¥20,682
¥77,306 total
includes taxes & fees
Jun 1 - Jun 2
Charles Cottage Near Warren St New Renovation

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is ¥23,831
¥60,732 total
includes taxes & fees
May 12 - May 13
Near Tanglewood: Historic Summer Retreat

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, (14 reviews)
"Very nice cabin, responsive host."
United States
Nick R.
The price is ¥27,889
¥65,105 total
includes taxes & fees
Jun 1 - Jun 2
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is ¥31,336
¥56,970 total
includes taxes & fees
May 12 - May 13
Big farmhouse in the foothills of the Berkshires

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is ¥42,163
¥77,198 total
includes taxes & fees
May 13 - May 14
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is ¥27,497
¥65,367 total
includes taxes & fees
May 12 - May 13
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is ¥36,820
¥77,901 total
includes taxes & fees
May 19 - May 20
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ¥37,133
¥78,931 total
includes taxes & fees
May 12 - May 13
Cheerful 3-bedroom cottage with woodstove

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, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is ¥56,248
¥113,757 total
includes taxes & fees
May 13 - May 14
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ¥7,756
¥44,891 total
includes taxes & fees
May 14 - May 15
Real Estate: Therapy - Lake, Laundry, Love it

Discover Hudson CharmHouse,where Hudson's sophistication and historic charm meet

Discover Hudson CharmHouse,where Hudson's sophistication and historic charm meet
Hudson
The price is ¥32,433
¥71,421 total
includes taxes & fees
May 14 - May 15
Discover Hudson CharmHouse,where Hudson's sophistication and historic charm meet

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
Hillsdale
10.0 out of 10, Exceptional, (128 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is ¥41,599
¥72,387 total
includes taxes & fees
May 17 - May 18
Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

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 ¥26,792
¥46,327 total
includes taxes & fees
May 13 - May 14
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ¥42,930
¥88,933 total
includes taxes & fees
May 12 - May 13
Treetop Hideaway in Tyringham
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

Find out more about Great Barrington

Great Barrington Vacation Homes information

Number of reviews
515
Accommodation
518 Vacation Homes
Lowest Price
¥22,146
Highest Price
¥208,108