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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for The Berkshires cottages

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

1. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is AU$812
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake
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$795
includes taxes & fees
18 Oct - 19 Oct
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
An outdoor patio with a fire pit, a grill, and outdoor furniture.

3. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is AU$539
includes taxes & fees
22 Oct - 23 Oct
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
A house with a porch and a small shed in the background.

4. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
Waterfront Lake Cottage - Lake Access -Kayaks
A two-story house with a balcony, a chimney, and a window with a view.

5. 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$2,582
includes taxes & fees
18 Oct - 19 Oct
Berkshires farm, 30+ guests, 50 acres
A wooden deck with a table, benches, and outdoor furniture.

6. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
The price is AU$786
includes taxes & fees
8 Nov - 9 Nov
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
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

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."
Christopher 3-night trip
Posted 9 hours ago
Jiminy Peak Mountain Resort

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
55
Accommodation
86 Cottages
Lowest Price
AU$539
Highest Price
AU$2,582

Frequently asked questions

How much do cottages in The Berkshires cost?
Cottages in The Berkshires range between AU$539 and AU$2,582 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 86 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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