A lake surrounded by autumn-colored trees and hills.

Search Cheshire Cottage Rentals from CA $777

  • 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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Cheshire 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 CA $314
CA $777 total
includes taxes & fees
Jul 26 - Jul 27
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
United States
Christine P.
The price is CA $491
CA $896 total
includes taxes & fees
Aug 6 - Aug 7
Beachwood Cottage
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 CA $2,137
CA $3,729 total
includes taxes & fees
Aug 5 - Aug 6
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 Cheshire Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"This was a beautiful hotel close to the best part of North Adams. The gallery on the lobby floor gives it an upscale vibe but without too high a price tag. It was very convenient for our college visit to Williams College. It was very quiet even directly across from the elevator. The beds were very comfortable. The coffee was good. But,my one note would be there wasn't anything else offered for breakfast that my picky eater teenager would eat."
Sara 1-night trip
Posted 1 hour ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Cheshire

Cheshire Cottages information

Number of reviews
Accommodation
88 Cottages
Lowest Price
CA $777
Highest Price
CA $777

Frequently asked questions

How much do cottages in Cheshire cost?
Cottages in Cheshire range between CA $777 and CA $777 per night. These properties offer a chance to get in touch with nature — at a price you can afford. 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.
Why book your cottage in Cheshire with Expedia?
We think that a vacation should be stress-free, so if you're seeking cottages in Cheshire at a great price, Expedia has your back. Save those pennies and stay in an inexpensive option far away from the city rush, or splurge on a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Cheshire?
An excellent way to uncover cheap cottages in Cheshire is with Expedia's handy filter tool. Narrow your search by budget, amenities and star rating to nab excellent rates in a couple of clicks.
What is there to do in Cheshire near my cottage?
If you're eager to see the sights of Cheshire, don't miss St Mary's of the Assumption Church. It's a winner among visitors and locals alike.

Explore a world of travel with Expedia