Holiday Rentals in Great Barrington
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Unlock member prices with Mates Rates
You could save 10% or more on over 100,000 hotels right now.
Check rental availability in Great Barrington
Holiday Rentals in Great Barrington

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

Peaceful Retreat Compound 10 Minutes to Great Barrington!

Great Barrington Get Away

The Ponds at Foxhollow

Micosta Leisure Inn

Peace and quiet on the lake

The Kemble- Built by a US Secretary of State in Lenox

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

Charming 3-bedroom Cabin for nature lovers

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Other types of properties in Great Barrington you may be interested in

Quality Inn
Holiday Accommodation Great Barrington
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Great Barrington are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Great Barrington itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Great Barrington holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Great Barrington, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Great Barrington with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.










