Search Vacation Homes in Great Barrington

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Great Barrington vacation homes

Fridge, microwave, oven, stovetop

Vacation Home in Great Barrington

Home in 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
Interior

Vacation Home in Great Barrington

Family Ski Getaway in the Berkshires
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 ￥31,529
￥46,349 total
includes taxes & fees
Jan 26 - Jan 27
Family Ski Getaway in the Berkshires
TV, fireplace, printers

Vacation Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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
Smart TV, DVD player, books, stereo

Vacation Home in Great Barrington

Great Barrington Get Away
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
3 bedrooms, iron/ironing board, WiFi, bed sheets

Vacation Home in Great Barrington

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

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
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
Smart TV, books

Vacation Home in Sherwood Forest

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

Vacation Home in Hudson

All the comforts of home
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
Interior

Vacation Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries
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
Exterior

Vacation Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
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
Interior

Vacation Home in Housatonic

Sweet Cozy Victorian in Housatonic. Close to everything.
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.
Interior

Vacation Home in Spencertown

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

Vacation Home in Russell

Big farmhouse in the foothills of the Berkshires
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
Fridge, microwave, stovetop, dishwasher

Vacation Home in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
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
Smart TV, books

Vacation Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
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!
Property grounds

Vacation Home in Chatham

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

Vacation Home in Stottville

Hudson Hot Tub & Pet Escape
The price is ￥23,580
￥45,113 total
includes taxes & fees
Jan 25 - Jan 26
Hudson Hot Tub & Pet Escape
Exterior

Vacation Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
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
Interior

Vacation Home in East Chatham

Luxury Barn Retreat — All-Season Escape Awaits!
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!
Outdoor dining

Vacation Home in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Barrington Hotel Reviews

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10/10 Excellent
"We really enjoyed our stay in Great Barrington. The location was excellent—close to the mountain and convenient to restaurants and town—and the house was a great fit for our family. Everything was comfortable and made for an easy, relaxing stay. One small thing to note is that the office area with the two twin beds is more of a pass-through space between rooms and doesn’t have blinds, but it didn’t take away from our overall experience. We’d happily stay here again."
Anonymous traveler 3-night trip
Posted 23 hours ago
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Find out more about Great Barrington

Great Barrington Vacation Homes information

Number of reviews
309
Accommodation
446 Vacation Homes
Lowest Price
￥22,008
Highest Price
￥207,448