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!
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
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$113 |
Highest Price | AU$351 |
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 |
Holiday Homes in Great Barrington
Top Locations for Holiday Homes in Great Barrington
More accommodations in Great Barrington
Top trending hotels in Great Barrington
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Monument Mountain Motel
More ways to explore Great Barrington
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.