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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 ¥23,112
¥39,628 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
9.4 out of 10, Exceptional, (8 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥31,529
¥46,349 total
includes taxes & fees
Jan 26 - Jan 27
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 ¥88,562
¥207,448 total
includes taxes & fees
Jan 25 - Jan 26
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is ¥48,267
¥85,915 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.
The price is ¥62,280
¥103,133 total
includes taxes & fees
Feb 8 - Feb 9
Cozy. Clean. Free bagel shop. 3 Fireplaces.

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ¥16,535
¥100,135 total
includes taxes & fees
Jan 25 - Jan 26
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 ¥24,943
¥58,991 total
includes taxes & fees
Jan 25 - Jan 26
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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 ¥16,535
¥22,008 total
includes taxes & fees
Jan 26 - Jan 27
All the comforts of home

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 ¥20,879
¥57,388 total
includes taxes & fees
Jan 25 - Jan 26
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is ¥16,816
¥52,316 total
includes taxes & fees
Jan 25 - Jan 26
Near Tanglewood: Historic Summer Retreat

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 ¥21,020
¥41,741 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 ¥33,164
¥42,375 total
includes taxes & fees
Jan 25 - Jan 26
Suite 3 - Quiet and private accommodations in a country setting.

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is ¥25,223
¥49,537 total
includes taxes & fees
Jan 26 - Jan 27
Big farmhouse in the foothills of the Berkshires

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
8.0 out of 10, Very Good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is ¥27,248
¥86,504 total
includes taxes & fees
Jan 25 - Jan 26
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 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 ¥28,026
¥71,653 total
includes taxes & fees
Jan 26 - Jan 27
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
The price is ¥27,248
¥47,607 total
includes taxes & fees
Jan 26 - Jan 27
Renovated house. Built in 1890s. No neighbors in sight.

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
The price is ¥23,160
¥44,310 total
includes taxes & fees
Jan 25 - Jan 26
Hudson Hot Tub & Pet Escape

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Goshen
The price is ¥37,134
¥78,477 total
includes taxes & fees
Jan 25 - Jan 26
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
The price is ¥52,160
¥97,656 total
includes taxes & fees
Jan 26 - Jan 27
Luxury Barn Retreat — All-Season Escape Awaits!

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 ¥41,899
¥76,889 total
includes taxes & fees
Jan 26 - Jan 27
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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
309
Accommodation
529 Vacation Homes
Lowest Price
¥22,008
Highest Price
¥207,448