Great Barrington Condo Rentals

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

Condo Rentals in Great Barrington

🌞Views! 2mi2Ski+Dtw! Great 1BR OpenLR/DR/Kit! FP,HPool,Htub,Gym,PetsOk,EVchg🌞!

Pittsfield MA

With a stay at this condo, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center and Guido's Marketplace.

Pool

Hot Tub

Tranquil Lakeside Escape in the Berkshires

Lenox MA

Located in Lenox, this condo is within a 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

Pool

Kitchen

Peaceful 1BR Condo with Pond View

Lenox MA

Located in Lenox, this condo is within a 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

Pool

Kitchen

Perfect for Winter Skiing!!

Pittsfield MA

With a stay at this condo in Pittsfield, you'll be within a 15-minute drive of Tanglewood Music Center and Bousquet Ski Area.

Pool

Kitchen

Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025

Pittsfield MA

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

Pool

Hot Tub

Sunny Victorian Studio in Pacific Heights

Germantown NY

With a stay at this condo in Germantown, you'll be within a 15-minute drive of Tousey Winery and Claverack Library.

Kitchen

Washer

Spacious 4-bedroom condo with AC and WiFi in Litchfield County

Torrington CT

Located in Torrington, this condo is a 4-minute drive from Burr Pond State Park and 7 minutes from Highland Lake.

Pool

Washer

Cozy Condo, walk to town, private and bright

Lenox MA

Located in Lenox, this condo is within a 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

Washer

Dryer

Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood

Lee MA

Located in Lenox, this condo is within a 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

Pool

Kitchen

Condo with Resort Amenities in Lenox

Lenox MA

When you stay at this condo in Lenox, you'll be in the mountains, within a 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

Pool

Hot Tub

Cozy Condo with resort amenities

Lenox MA

With a stay at this condo in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

Pool

Hot Tub

Lots of snow! Ski, snowshoe/ heated pool - fabulous in beautiful Stockbridge

West Stockbridge MA

With a stay at this condo in Lenox, you'll be a 4-minute drive from Tanglewood Music Center and 9 minutes from National Shrine of the Divine Mercy.

Pool

Kitchen

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.