Book Holiday Homes in Great Barrington

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Featured Holiday Homes in Great Barrington

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$360 per night from 3 May to 4 May
AU$360
includes taxes & fees
3 May - 4 May
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!!
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
Mountain View Getaway

Mountain View Getaway

West Cornwall
Located in Cornwall, this vacation home is on a lake, within a 15-minute drive of Music Mountain and West Cornwall Covered Bridge.
Mountain View Getaway
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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.
Peace and quiet on the lake

Peace and quiet on the lake

Becket
With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Peace and quiet on the lake
Lakeside Retreat Just You, The Lake & The View!

Lakeside Retreat Just You, The Lake & The View!

Great Barrington
Located in Great Barrington, this vacation home is on the waterfront, within a 10-minute drive of Art et Industrie and Housatonic River.
Lakeside Retreat Just You, The Lake & The View!
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!
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Athens
With a stay at this vacation home in Athens, you'll be on the waterfront, just a 1-minute walk from Sleepy Hollow Lake and 13 minutes by foot from Hudson ...
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Heart of Lenox Walk to Town Cozy Cottage!

Heart of Lenox Walk to Town Cozy Cottage!

Lenox
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and The Bookstore.
Heart of Lenox Walk to Town Cozy Cottage!
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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
583 Holiday Homes
Lowest Price
AU$131
Highest Price
AU$360
Popular accommodation
Berkshire Village Carriage House - Super Private!!, 4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi, Mountain View Getaway, Spectacular views and close to Great Barrington., Peace and quiet on the lake, Lakeside Retreat Just You, The Lake & The View!, COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!, Heart of Lenox Walk to Town Cozy Cottage!

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$131 per night from 12 May to 13 May
AU$131
includes taxes & fees
12 May - 13 May
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 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 AU$217 per night from 1 May to 2 May
AU$217
includes taxes & fees
1 May - 2 May
With a stay at Holiday Inn Express Hotel & Suites Great Barrington by IHG in Great Barrington, you'll be on a river, just steps from Housatonic River and a 3-minute ...
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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$262 per night from 27 May to 28 May
AU$262
includes taxes & fees
27 May - 28 May
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
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The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$133 per night from 13 May to 14 May
AU$133
includes taxes & fees
13 May - 14 May
Located in Great Barrington, The Little Lion is within a 10-minute drive of Ski Butternut and Berkshire Botanical Garden.
The Little Lion
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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.