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Find holiday rentals that suit your style

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Cabins
Cabins
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Apartments
Apartments

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 cabin with a wooden deck, a covered porch, and a gravel driveway.

1. 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 NZ$1,050
includes taxes & fees
17 Nov - 18 Nov
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A two-story house with a balcony, a chimney, and a window with a view.

2. 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 NZ$3,271
includes taxes & fees
1 Dec - 2 Dec
Berkshires farm, 30+ guests, 50 acres
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 NZ$827
includes taxes & fees
9 Nov - 10 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?

Prices for cottages in Great Barrington range between NZ$827 and NZ$3,271 per night. Whatever your budget, you're sure to find the perfect place to immerse yourself in nature. These prices were 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?

Make use of your holiday days and pick from cottages in Great Barrington. Picturing a place where you can immerse yourself in nature? Expedia will help you find your ideal retreat in a few simple clicks.

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

Great Barrington has enough sights and experiences to keep you on the go for weeks, beginning with Ski Butternut. Housatonic River Walk, Mahaiwe Performing Arts Centre and Lake Buel are other fantastic attractions. If you're staying a while longer, Lake Mansfield Park and W.E.B. Du Bois Boyhood Homesite are great additions to your itinerary.