Book Holiday Homes in Great Barrington

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Great Barrington

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville
With a stay at this vacation home in Copake Lake, you'll be within a 5-minute drive of Copake Lake and Mosquito Island.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Wyndhurst Golf & Club and Berkshire Scenic Railway Museum.
Amore Estate - beautiful room with many places to explore and relax in.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie
The price is AU$877 per night from 6 Dec to 7 Dec
AU$877
includes taxes & fees
6 Dec - 7 Dec
Located in Valatie, this vacation home is on the waterfront, a 1-minute drive from Kinderhook Lake and 6 minutes from Valatie Family Care.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Save an average of 15% on thousands of hotels when you're signed in
Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

Stockbridge
Located in South Lee, this vacation home is in a rural location, within a 5-minute drive of Berkshire Botanical Garden and Housatonic River.
Secluded Family Home in Serene Stockbridge Woods
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$344 per night from 25 Nov to 26 Nov
AU$344
includes taxes & fees
25 Nov - 26 Nov
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Berkshire Botanical Garden and Tanglewood Music Center.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

Winchester
With a stay at this vacation home in Winsted, you'll be on the waterfront, just a 4-minute walk from Highland Lake and 12 minutes by foot from Winchester Historical ...
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

East Otis
With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from County Beach.
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Don't see what you're looking for?
See all available properties in Great Barrington
View all properties
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.

Great Barrington Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Great Barrington vacation homes are the perfect way for you to wing it.

Holiday houses in Great Barrington let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Great Barrington in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Great Barrington adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Great Barrington with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Great Barrington vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Great Barrington Holiday Homes essential information

Accommodation
457 Holiday Homes
Lowest Price
AU$114
Highest Price
AU$877
Popular accommodation
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, Amore Estate - beautiful room with many places to explore and relax in., Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, Secluded Family Home in Serene Stockbridge Woods, Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!, 4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

Top trending hotels in Great Barrington

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 8 Dec to 9 Dec
AU$122
includes taxes & fees
8 Dec - 9 Dec
With a stay at Quality Inn in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 7 minutes by foot from ...
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Fully refundable
The price is AU$203 per night from 3 Dec to 4 Dec
AU$203
includes taxes & fees
3 Dec - 4 Dec
With a stay at Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel in Great Barrington, you'll be on a river, just steps from Housatonic River ...
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$261 per night from 5 Dec to 6 Dec
AU$261
includes taxes & fees
5 Dec - 6 Dec
A stay at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires places you in the heart of Great Barrington, within a 5-minute drive of Housatonic ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Save an average of 15% on thousands of hotels when you're signed in
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$114 per night from 25 Nov to 26 Nov
AU$114
includes taxes & fees
25 Nov - 26 Nov
With a stay at Monument Mountain Motel in Great Barrington, you'll be a 4-minute walk from Housatonic River and within a 5-minute drive of Housatonic River ...
Monument Mountain Motel
Don't see what you're looking for?
See all available properties in Great Barrington
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.