Search Condos Rentals in Great Barrington

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Great Barrington Condo Rentals

Tranquil Lakeside Escape in the Berkshires
Property grounds

Tranquil Lakeside Escape in the Berkshires

10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
Tranquil Lakeside Escape in the Berkshires
Peaceful 1BR Condo with Pond View
Property grounds

Peaceful 1BR Condo with Pond View

8.0 out of 10, Very good, (1)
"The location was very close to Tanglewood and The Mount, but the front drive off the main road was really dark, no street lights, so we missed our turn a few times but did eventually find the place. The community was pretty and tranquil, we did not hear any noise at all. The WiFi was a little wonky but no big deal because we were able to get cell service. "
Peaceful 1BR Condo with Pond View
Perfect for Winter Skiing!!
Fridge, microwave, oven, stovetop

Perfect for Winter Skiing!!

Perfect for Winter Skiing!!
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (2)
"It is located near everything"
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.
Living area

Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.

Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.
Spacious 4-bedroom condo with AC and WiFi in Litchfield County
Outdoor dining

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

Spacious 4-bedroom condo with AC and WiFi in Litchfield County
Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025
Microwave, oven, stovetop

Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025

Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025
Cozy Condo with resort amenities
Property grounds

Cozy Condo with resort amenities

Cozy Condo with resort amenities
Cozy Condo, walk to town, private and bright
Dishwasher

Cozy Condo, walk to town, private and bright

Cozy Condo, walk to town, private and bright
Sunny Victorian Studio in Pacific Heights
1 bedroom, iron/ironing board, free WiFi, bed sheets

Sunny Victorian Studio in Pacific Heights

Sunny Victorian Studio in Pacific Heights
Condo with Resort Amenities in Lenox
Property grounds

Condo with Resort Amenities in Lenox

Condo with Resort Amenities in Lenox
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Barrington Hotel Reviews

The Constance by the Lenox Collection

The Constance by the Lenox Collection

10/10 Excellent
"Great place , love it, will return"
Jelena 2-night trip
Posted 2 days ago
The Constance by the Lenox Collection