Search Cheshire Cottage Rentals from CA $321

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Cheshire 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, (1 review)
"This place is simply fantastic. If you are looking for quiet...and I mean ABSOLUTE quiet...this is your place! Nestled just five minutes south of Readsboro, VT, Brookside Cottage is the place to get disconnected and just breathe a bit. Our family needed this place...I needed to be here...with our kids growing up so fast, now at 14 and 11, my wife and I just wanted to have a few days to be together, play some games, watch some movies, and enjoy each other's company. I'm convinced we found the...
United States
Jason H.
The price is CA $184
CA $321 total
includes taxes & fees
May 10 - May 11
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 CA $267
CA $755 total
includes taxes & fees
May 10 - May 11
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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 $1,666
CA $2,906 total
includes taxes & fees
May 14 - May 15
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.
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Top Cheshire Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Lovely “old” hotel, used to be a men’s clothing store, but it has been remodelled into an exceptional place to stay in downtown Pittsfield. Our room was huge, clean, comfy beds, nice sitting area, desk area, coffee/tea area, and shelves of books! The bathroom was huge, clean, and well-supplied. There was a mini bar but we didn’t use it. Private parking in rear with direct access to hotel lobby. Staff was helpful, friendly, and professional. Great place to stay!"
Deborah 1-night trip
Posted 4 hours ago
Hotel On North

Find out more about Cheshire

Cheshire Cottages information

Number of reviews
1
Accommodation
80 Cottages
Lowest Price
CA $321
Highest Price
CA $2,906

Frequently asked questions

How much do cottages in Cheshire cost?
Cottages in Cheshire range between CA $321 and CA $2,906 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.

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