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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Great Barrington cottages

A two-story house with a balcony, a chimney, and a window with a view.

1. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is AU$2,661
includes taxes & fees
1 Dec - 2 Dec
Berkshires farm, 30+ guests, 50 acres
A cabin with a wooden deck, a covered porch, and a gravel driveway.

2. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is AU$856
includes taxes & fees
9 Nov - 10 Nov
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

3. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
The price is AU$655
includes taxes & fees
11 Nov - 12 Nov
Sharon Retreat w/ Private Yard
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.
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Learn more about Great Barrington

Tucked in the Berkshires, this charming town blends historic Main Street shopping with easy access to Monument Mountain's panoramic hiking trails. Visit in autumn when the maple-lined streets burst with colour, or catch performances at the Mahaiwe Theatre housed in a beautifully restored 1905 building.

See all hotels in Great Barrington
A building with a marquee sign reading "MAHAIWE Performing Arts Center" and a smaller sign for "Black Violin" performances.

Frequently Asked Questions

How much do cottages in Great Barrington cost?

Cottages in Great Barrington range between AU$655 and AU$2,661 per night. These stays offer a chance to get in touch with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many cottages are there in Great Barrington?

You'll find cottages in Great Barrington. No matter if you're travelling with the family or planning a weekend retreat with your pals, Expedia will help you find the ideal space to escape the hustle and bustle.

What is there to do in Great Barrington near my cottage?

There are loads of terrific things to sink your teeth into in Great Barrington. You won't want to miss popular attractions like Ski Butternut, Catamount Ski Area and Norman Rockwell Museum. Bash Bish Falls State Park, Mahaiwe Performing Arts Centre and Berkshire Theatre Festival also lure many visitors.