Great Barrington Vacation Rentals

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Our top choices for Great Barrington vacation rentals

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"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 ¥23,578
¥40,097 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Home in Great Barrington

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (6)
The price is ¥29,824
¥44,113 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Family Ski Getaway in the Berkshires

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1)
"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 ¥53,020
¥91,621 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (25)
"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 ¥48,341
¥86,397 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Great Barrington Get Away

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
The price is ¥70,169
¥88,320 total
includes taxes & fees
Dec 28 - Dec 29
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

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)
"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 ¥88,278
¥198,415 total
includes taxes & fees
Jan 8 - Jan 9, 2026
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)
"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.
The price is ¥102,896
¥217,960 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Catamount, Zip Line, Private Setting, Book Now!

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is ¥35,132
¥58,456 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Sugar Shack - 300 square feet of pure sweetness.

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (6)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is ¥35,132
¥58,106 total
includes taxes & fees
Jan 5 - Jan 6, 2026
BLUSH: Boutique TINY home*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is ¥35,132
¥64,443 total
includes taxes & fees
Jan 13 - Jan 14, 2026
HunnyHAUS: Deluxe TINY*private spa*walk to town

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (132)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is ¥20,263
¥22,696 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Micosta Leisure Inn

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
Goshen
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ¥13,818
¥96,928 total
includes taxes & fees
Jan 4 - Jan 5, 2026
CT Gate House Goshen CT, Gate House Goshen CT

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (46)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is ¥13,912
¥26,305 total
includes taxes & fees
Dec 28 - Dec 29
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

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)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ¥22,765
¥58,391 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers
Stephentown
7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is ¥24,171
¥48,813 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Charming 3-bedroom Cabin for nature lovers

All comforts of home

All comforts of home
Hudson
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is ¥15,298
¥20,625 total
includes taxes & fees
Jan 8 - Jan 9, 2026
All comforts of home

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29)
"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 ¥16,561
¥22,042 total
includes taxes & fees
Jan 8 - Jan 9, 2026
All the comforts of home

Pet-Friendly Hudson Escape w/ Hot Tub

Pet-Friendly Hudson Escape w/ Hot Tub
2.0 star property
Stottville
The price is ¥28,105
¥55,142 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Pet-Friendly Hudson Escape w/ Hot Tub

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)
"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 ¥25,014
¥61,253 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is ¥24,794
¥31,262 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Brooks Motel: Exceptional Suite
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

Search for holiday rentals in Great Barrington on Expedia! You can easily find your home rentals, villas, holiday apartments in Great Barrington using one of the methods below:

  • View our selection of featured holiday rentals in Great Barrington
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Look no further and take a look at our great range of rental properties in Great Barrington!

Frequently asked questions

Can I find a vacation rental in Great Barrington?

Yes, there are vacation rentals close to the most popular points of interest in Great Barrington, or you can select a secluded option if you're looking for relaxation. Visitors like the top-notch restaurants and live music in Great Barrington. Leave some time to check out the ski slopes and theater scene during your trip.

What are some of the best vacation rentals in Great Barrington?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This highly rated vacation home rental in Great Barrington offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Great Barrington are Family Ski Getaway in the Berkshires and The Great Escape Ski Cottage w/HOT TUB @ Great Barrington .

How many vacation rentals are there in Great Barrington?

With 96 Expedia vacation rentals, you're sure to find just the right place for your Great Barrington stay.

What can I see and do in Great Barrington?

Cultural attractions include Mahaiwe Performing Arts Center and Art et Industrie, whereas Housatonic River Walk and Housatonic River are a couple of picturesque spots to enjoy the outdoors. Lake Mansfield Park and Ski Butternut are other places to visit while you're in town.

What are vacation rentals like in Great Barrington?

Vacation rentals are privately owned properties you can reserve for several days or more in Great Barrington. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family getaway.