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^
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.
Accommodation | 399 Holiday Homes |
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Lowest Price | AU$114 |
Highest Price | AU$701 |
Popular accommodation | Berkshire Village Carriage House - Super Private!!, Fox Hollow Luxury Ranch Laurel Lake, Peace and quiet on the lake, Cheerful 3-bedroom cottage with woodstove, Remodeled Lakefront retreat w/firepit, close to skiing, golf, and hiking trails!, Bright, Airy Home with TONS of character in Hudson, NY - 5 min from Warren St, Stockbridge Home: Walk to Town Beach!, Restored 1810 Farmhouse in Hillsdale, NY, Mason's Lodge · Luxury Home - 3 Fireplaces Mins to Ski & Town |
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.