Photo by Ed Gaffny

Search Cottages in Cheshire

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Browse Select Cheshire Cottages

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Charlemont Retreat on Chickley River w/ EV Charger
3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge Home: Walk to Town Beach!
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Peaceful Family Home w/ Fire Pit & Large Yard
3.0 star property
Peaceful Family Home w/ Fire Pit & Large Yard
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Berkshire Hideaway w/ Fire Pit & Playground!
3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Berkshires Cabin 2 Mi to Appalachian Trail!
3.0 star property
Berkshires Cabin 2 Mi to Appalachian Trail!
Lakeside Berkshires Home Near Hiking & Skiing!
3.0 star property
Lakeside Berkshires Home Near Hiking & Skiing!
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
3.0 star property
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
Stylish Rustic Retreat w/ Breathtaking Mtn Views!
3.0 star property
Stylish Rustic Retreat w/ Breathtaking Mtn Views!
Cozy Southern Vermont Home w/ On-site Trails
3.0 star property
Cozy Southern Vermont Home w/ On-site Trails
Cozy Stockbridge Cabin - Walk to Beach & Lake!
3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Historic New Lebanon Hideaway on 33 Private Acres!
3.0 star property
Historic New Lebanon Hideaway on 33 Private Acres!
Elegant Pittsfield Home Near Downtown & Skiing!
3.0 star property
Elegant Pittsfield Home Near Downtown & Skiing!
Picturesque Cottage With Sunroom on Ashmere Lake!
3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
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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Other property types in Cheshire

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1737)
"The staff was very nice! And the room was spacious and clean with plenty of amenities. "
The price is ฿5,694
฿6,583 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (912)
"Very quiet and clean. would definitely go back. "
The price is ฿5,019
฿5,505 total
includes taxes & fees
6 Nov - 7 Nov
Jiminy Peak Mountain Resort
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.

Frequently asked questions

How much do cottages in Cheshire cost?
You can expect to pay between and per night for cottages in Cheshire. Whatever your budget, the perfect stay is just a few clicks away on Expedia. 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?
Reserving a cottage in Cheshire is as easy as working out your travel dates and picking an ideal place for outdoor fun and relaxation. From upmarket retreats to budget-friendly properties and cottages that offer conveniences like a kitchen, Expedia has something for all styles and tastes. As for irresistible deals? We’ve got your back!
How can I find cheap cottages in Cheshire?
With Expedia’s useful filter tool, locating cheap cottages in Cheshire is a cinch. To discover accommodation that are very pocket friendly, refine your search by amenities, star rating and budget.
What is there to do in Cheshire near my cottage?
After you’ve checked in to your hotel, head out and explore the fun things Cheshire has to offer. St Mary’s of the Assumption Church is a popular attraction to add to your travel itinerary.