Search The Berkshires Cottage Accommodations

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for The Berkshires cottages

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$828
includes taxes & fees
19 Jan - 20 Jan
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Terrace/patio

Pet-Friendly Hudson Escape w/ Hot Tub

Pet-Friendly Hudson Escape w/ Hot Tub
2.0 star property
Stottville
The price is AU$522
includes taxes & fees
9 Feb - 10 Feb
Pet-Friendly Hudson Escape w/ Hot Tub
Exterior

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Nassau
10.0 out of 10, Exceptional, (2 reviews)
"Cozy home on the lake."
United States
Terry O.
The price is AU$553
includes taxes & fees
16 Jan - 17 Jan
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Exterior

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
2.0 star property
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is AU$2,713
includes taxes & fees
4 Feb - 5 Feb
Berkshires farm, 30+ guests, 50 acres
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top The Berkshires Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Accommodating staff!"
Kelly 1-night trip
Posted 22 hours ago
The Williams Inn

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
2
Accommodation
84 Cottages
Lowest Price
AU$522
Highest Price
AU$2,713

Frequently asked questions

How much do cottages in The Berkshires cost?
Cottages in The Berkshires range between AU$522 and AU$2,713 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 84 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.

Explore a world of travel with Expedia