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Our top choices for Great Barrington vacation homes

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ¥23,054
¥39,529 total
includes taxes & fees
Jan 26 - Jan 27
Home in Great Barrington

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥32,019
¥47,069 total
includes taxes & fees
Jan 19 - Jan 20
Family Ski Getaway in the Berkshires

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, (3 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 ¥89,939
¥210,673 total
includes taxes & fees
Jan 20 - Jan 21
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Catamount, Zip Line, Private Setting, Book Now!

Catamount, Zip Line, Private Setting, Book Now!
Egremont
10.0 out of 10, Exceptional, (7 reviews)
"This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."
United States
Jason W.
Catamount, Zip Line, Private Setting, Book Now!

Peaceful, Post and Beam Loft, Sleeps 9

Peaceful, Post and Beam Loft, Sleeps 9
New Marlborough
9.8 out of 10, Exceptional, (22 reviews)
"A very nice post & beam Berkshire house, quiet, clean, great acerage and amenities.Lucas was very accessible to handle minor issues quickly."
United States
HARRELL O.
Peaceful, Post and Beam Loft, Sleeps 9

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is ¥49,017
¥87,780 total
includes taxes & fees
Jan 25 - Jan 26
Great Barrington Get Away

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.
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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 ¥25,615
¥62,699 total
includes taxes & fees
Feb 2 - Feb 3
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
Goshen
9.4 out of 10, Exceptional, (8 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ¥16,792
¥101,691 total
includes taxes & fees
Jan 22 - Jan 23
CT Gate House Goshen CT, Gate House Goshen CT

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is ¥25,331
¥60,970 total
includes taxes & fees
Jan 21 - Jan 22
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is ¥22,769
¥60,566 total
includes taxes & fees
Jan 19 - Jan 20
Historic Berkshires Home Near Tanglewood, Trails & Wineries

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is ¥18,658
¥24,439 total
includes taxes & fees
Feb 2 - Feb 3
All the comforts of home

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.2 out of 10, Wonderful, (25 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is ¥18,927
¥55,733 total
includes taxes & fees
Jan 20 - Jan 21
Near Tanglewood: Historic Summer Retreat

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.4 out of 10, Exceptional, (3 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is ¥28,462
¥72,767 total
includes taxes & fees
Jan 19 - Jan 20
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Monterey
10.0 out of 10, Exceptional, (1 review)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
2.0 star property
Stephentown
8.0 out of 10, Very Good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is ¥27,671
¥89,077 total
includes taxes & fees
Jan 19 - Jan 20
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is ¥21,346
¥42,389 total
includes taxes & fees
Feb 1 - Feb 2
Sweet Cozy Victorian in Housatonic. Close to everything.

Suite 3 - Quiet and private accommodations in a country setting.

Suite 3 - Quiet and private accommodations in a country setting.
Spencertown
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
The price is ¥33,680
¥43,034 total
includes taxes & fees
Jan 25 - Jan 26
Suite 3 - Quiet and private accommodations in a country setting.

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
2.0 star property
Stottville
The price is ¥26,208
¥53,411 total
includes taxes & fees
Jan 19 - Jan 20
Hudson Hot Tub & Pet Escape

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ¥34,470
¥55,459 total
includes taxes & fees
Feb 18 - Feb 19
3-bedroom house in beautiful Berkshires, close to amenities!
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
187
Accommodation
529 Vacation Homes
Lowest Price
¥24,439
Highest Price
¥210,673