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Check prices for these dates

In two weeks
19 June - 21 June
In two months
31 July - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for The Berkshires cottages

Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (2 reviews)
"It was an excellent place to stay. Super comfy and quiet, falling asleep to the sound of the creek. Well equipped with everything you need. Good fast wifi. Excellent value for the money. Great place if you want to really get away from it all."
United States
Seva L.
The price is AU$327
includes taxes & fees
7 June - 8 June
Brookside cottage near the mountains and outdoor recreation
House (3 Bedrooms) | Interior

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$771
includes taxes & fees
2 June - 3 June
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (81 reviews)
"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."
United States
Karissa A.
The price is AU$530
includes taxes & fees
2 June - 3 June
Perfect for a peaceful get away in clean fresh Vermont air!
Terrace/patio

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is AU$510
includes taxes & fees
7 June - 8 June
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Exterior

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$2,542
includes taxes & fees
2 June - 3 June
Berkshires farm, 30+ guests, 50 acres
House (4 Bedrooms) | Interior

3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is AU$1,025
includes taxes & fees
4 June - 5 June
3 Mi to Mount Snow: Spacious West Dover Home
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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Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"It was nice"
BRIAN 4-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
83
Accommodation
85 Cottages
Lowest Price
AU$327
Highest Price
AU$2,542

Frequently asked questions

How much do cottages in The Berkshires cost?
Cottages in The Berkshires range between AU$327 and AU$2,542 per night. These stays offer a chance to get reacquainted 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 The Berkshires?
Select from 85 cottages in The Berkshires. Whether you're travelling with your family, as a duo or with a group of pals, Expedia makes it a breeze to find the ideal space.
What is there to do in The Berkshires near my cottage?
No matter your interests, there are so many things to keep you busy in The Berkshires. If you're headed to Williamstown, stop by Sterling and Francine Clark Art Institute, Williams College Museum of Art and Williamstown Historical Museum. Spending your vacay in Pittsfield? Bousquet Ski Area, Berkshire Museum and Colonial Theatre are top attractions in this city.

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