Book Holiday Homes in Great Barrington

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Featured Holiday Homes in Great Barrington

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
The price is NZ$1,208 per night from 11 Aug to 12 Aug
NZ$1,208
11 Aug - 12 Aug
includes taxes & fees
Enjoy laundry facilities and in-room fireplaces. Popular attractions Tanglewood Music Center and Berkshire Mountain Country Store are located nearby.
Spacious 5-bedroom house in charming Lee with WiFi
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont
Stay at this vacation home in Egremont. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Thom Reed UFO Monument Park and W.E.B. Du Bois ...
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Art et Industrie and Monument ...
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

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

Valatie
Stay at this vacation home in Valatie. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Kinderhook Lake and Valatie Free Library are located ...
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Berkshire Ashmere Lake lodging. Quiet  room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
Stay at this vacation home in Hinsdale. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Bas Ridge Golf Course and Wahconah Falls State Park ...
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Charming cottage with lake access, wood burning fire place, and WiFi

Charming cottage with lake access, wood burning fire place, and WiFi

2 out of 5
Elizaville
Stay at this vacation home in Elizaville. Enjoy a garden, laundry facilities, and patios. Popular attractions Tousey Winery and West Beach are located ...
Charming cottage with lake access, wood burning fire place, and WiFi
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Russell
The price is NZ$615 per night from 5 Aug to 6 Aug
NZ$615
5 Aug - 6 Aug
includes taxes & fees
Stay at this vacation home in Russell. Enjoy a garden, laundry facilities, and patios. Our guests praise the property condition in our reviews. Popular attractions ...
Big farmhouse in the foothills of the Berkshires
Mountain View Getaway

Mountain View Getaway

West Cornwall
Book a stay at this ski vacation home in Cornwall. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Music Mountain and West Cornwall Covered ...
Mountain View Getaway
Taconic Hideaway – Swimming, BBQ Pit, Hiking

Taconic Hideaway – Swimming, BBQ Pit, Hiking

2 out of 5
Copake
Stay at this vacation home in Copake. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Copake Town Park and Copake Lake are located ...
Taconic Hideaway – Swimming, BBQ Pit, Hiking
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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
616 Holiday Homes
Lowest Price
NZ$175
Highest Price
NZ$1,208
Popular accommodation
Spacious 5-bedroom house in charming Lee with WiFi, Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT, Lakefront Berkshires Retreat w/ Deck, Dock & Boat!, Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. , Charming cottage with lake access, wood burning fire place, and WiFi, Big farmhouse in the foothills of the Berkshires, Mountain View Getaway, Taconic Hideaway – Swimming, BBQ Pit, Hiking

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 NZ$175 per night from 2 Sept to 3 Sept
NZ$175
2 Sept - 3 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Quality Inn
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 NZ$285 per night from 27 Aug to 28 Aug
NZ$285
27 Aug - 28 Aug
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Fully refundable
The price is NZ$262 per night from 2 Sept to 3 Sept
NZ$262
2 Sept - 3 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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Prospect Berkshires

Prospect Berkshires

2 out of 5
50 Prospect Lake Rd, Egremont, MA
The price is NZ$859 per night from 5 Aug to 6 Aug
NZ$859
5 Aug - 6 Aug
includes taxes & fees
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area ...
Prospect Berkshires
Don't see what you're looking for?
See all available properties in Great Barrington
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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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^Subject to availability and chosen travel dates.