Great Barrington Vacation Rentals

Name: Remodeled Lakefront retreat w/firepit, close to skiing, golf, and hiking trails!
Address: Copake

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Great Barrington

Peace and quiet on the lake

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.

Pet friendly

Free WiFi

Fox Hollow Luxury Ranch Laurel Lake

With a stay at this vacation home in Lenox, you'll be on a lake, within a 10-minute drive of Tanglewood Music Center and The Mount.

Pool

Pet friendly

Newly Renovated Family House On Highland Lake with Dock

With a stay at this vacation home in Winsted, you'll be on the beach, just steps from Highland Lake and a 2-minute drive from Winchester Historical Society.

Free WiFi

Outdoor Space

Hearts Desire is a furnished whole house in a small, colorful garden center.

With a stay at this vacation home in Lanesborough, you'll be on a lake, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State Reservation.

Berkshire Village Carriage House - Super Private!!

Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.

Free WiFi

Outdoor Space

Near Tanglewood: Historic Summer Retreat

$150

per night

May 15 - May 16

When you stay at this vacation home in New Lebanon, you'll be in the mountains, within a 10-minute walk of New Lebanon Town Hall and Shatford Memorial Park.

Pet friendly

Fireplace

Bright, Airy Home with TONS of character in Hudson, NY - 5 min from Warren St

$190

per night

May 15 - May 16

A stay at this vacation home places you in the heart of Hudson, within a 5-minute drive of Stoddard Corner and Columbia-Greene Hospital Foundation.

Dancing Horse Lodge

With a stay at this vacation home in Pittsfield, you'll be in the mountains, within a 15-minute drive of Tanglewood Music Center and Guido's Marketplace.

Stockbridge Home, Come Experience The Berkshires!

With a stay at this vacation home in Stockbridge, you'll be within a 15-minute drive of Tanglewood Music Center and Schantz Galleries.

Chic Pittsfield Home With A View!

With a stay at this vacation home in Pittsfield, you'll be near the beach, within a 15-minute drive of Tanglewood Music Center and Housatonic River.

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

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 River.

Remodeled Lakefront retreat w/firepit, close to skiing, golf, and hiking trails!

Located in Ancram, this vacation home is on a lake, within a 5-minute drive of New Forge State Forest and Copake Lake.

Don't see what you're looking for?

See all available properties in Great Barrington

View all properties

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.