Great Barrington Vacation Rentals

Compare 2 vacation rentals.

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Make Great Barrington your next getaway

Great Barrington, MA vacation rentals

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House rentals

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Great Barrington vacation rentals for every getaway

Popular

Dog-friendly Internet Lake view

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

House in Great Barrington

$543 avg / night

3.0 (4)

Great Barrington Lakeside Getaway w/ Kayak & Grill

House in Great Barrington

$614 avg / night

5.0 (3)

View all homes

Listings nearby Great Barrington

Water-View Home in the Berkshires

House in Sheffield

$449 avg / night

4.6 (5)

Ashley Falls Home w/ Fire Pit: Hike & Ski!

House in Sheffield

$508 avg / night

5.0 (3)

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Cottage in Monterey

$334 avg / night

4.8 (5)

Massachusetts Lake House w/ Dock - Pets Welcome!

House in Monterey

$1,101 avg / night

5.0 (2)

Vacation rentals near Great Barrington

Explore more vacation rental amenities in Great Barrington

Ocean view

Water view

Waterfront

A/C

Washer/dryer

Balcony

Bikes

Ping-pong table

Pool table

Tennis court

Recent Great Barrington vacation rental reviews

2nd year staying here for a 3 day family stay in GB. House is cozy, comfortable, and great setup for 10 people.

Suzanne . | Feb 2026

Lovely setting

Elizabeth . | Oct 2025

Great time at this location. Five girlfriends on a shopping trip. House was in a great location, fulky furnished with all you could want and more. Definetly a place you will be comfortable at and wonderful stay.

Annette . | Dec 2024

The home was beautiful with plenty of room for our family of 8 to spread out and relax. The kitchen was well-appointed, all linens and toiletries available. This is a perfect writer's retreat with so many windows, light coming in and beautiful scenery.

Amy . | Apr 2024

Great Barrington Frequently Asked Questions

Yes. 28 of our Great Barrington vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Great Barrington vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Great Barrington team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Great Barrington, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

24/7 support

Easy check-in

Professional cleaning

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