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Compare 57 Cottages in Cheshire with updated reviews, rates, and availability.

Charming historic cottage on scenic road to Mt. Greylock
Summer
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (103)
"Great cottage, pretty much at the foot of Mount Greylock - very spacious and comfortable - in the country but close to many of the towns of the Berkshires - the hosts Cheryl and Rich were very kind and informative about the area -thank you Cheryl and Rich - I hope to return sometime -"
Charming historic cottage on scenic road to Mt. Greylock
Cozy Berkshire cottage with fireplace.
Interior
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (22)
"We had a wonderful experience- house was clean and very comfy with all the amenities. Hosts went out of their way both before and during our stay to provide information and make sure all our needs were met! We enjoyed relaxing in the house and the location was also very close to many great Berkshires sights!! Highly recommend this listing! "
Cozy Berkshire cottage with fireplace.
Cozy cottage with pool, walking distance to lake
Dining
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (12)
"This was our second year in a row here! We already booked for next summer! Peaceful and calm. The pool is fantastic."
Cozy cottage with pool, walking distance to lake
Morgan House on Crooked Lake
Private kitchen
Morgan House on Crooked Lake
10.0 out of 10, Exceptional, (7)
"Kelly was an amazing host. She was incredibly inviting and friendly. If we needed anything, Kelly was there, ready to help. The house was beautiful and was perfect for a wedding weekend with our bridal party. We highly recommend Kelly and her wonderful house for anyone who wants a relaxing getaway or for a wedding party to stay and get ready for their big day on this beautiful lake."
Morgan House on Crooked Lake
Beachwood Cottage
Exterior detail
Beachwood Cottage
10.0 out of 10, Exceptional, (3)
"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."
Beachwood Cottage
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Outdoor dining
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!
Property grounds
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!
Outdoor dining
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
Living area
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
Cottage in the Clouds With Mountain Views
Fully stocked kitchen. Two skylights provide plenty of natural light
Cottage in the Clouds With Mountain Views
9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Living area
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!
Picturesque Cottage with Sunroom on Ashmere Lake!
Hinsdale Vacation Rental | 3BR | 2BA | 1,340 Sq Ft | Stairs Required
Picturesque Cottage with Sunroom on Ashmere Lake!
9.4 out of 10, Exceptional, (21)
"Everything was just like it was listed. We had trouble with the t.v. but other than that it was great. "
Picturesque Cottage with Sunroom on Ashmere Lake!
Stockbridge Home: Walk to Town Beach!
Exterior
Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge Home: Walk to Town Beach!
Private Lake Cottage on 3 acres w/350 sq. ft. deck
This living room has an oversized sectional with a large fireplace and smart TV.
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Pool
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
Terrace/patio
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!
Dining
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Family-Friendly Richmond Cottage w/ Private Yard
Richmond Vacation Rental | 2BR | 2BA | 1,750 Sq Ft | Stairs Required
Family-Friendly Richmond Cottage w/ Private Yard
2.0 star property
10.0 out of 10, Exceptional, (2)
"Excellent property: would have liked to stay longer. "
Family-Friendly Richmond Cottage w/ Private Yard
Berkshire Hideaway w/ Fire Pit & Playground!
Living area
Berkshire Hideaway w/ Fire Pit & Playground!
3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Peaceful Seasonal lake front cottage with view of Burden Lake
Terrace/patio
Peaceful Seasonal lake front cottage with view of Burden Lake
10.0 out of 10, Exceptional, (2)
"We had a great weekend stay at this beautiful lake house. The house is perfectly located directly on Burden Lake. The inside of the house was very clean and spacious with a nice nautical theme to it. The outside was equally as beautiful equipped with all the amenities to have an amazing outdoor weekend and a beautiful view of the lake. Kendra was an amazing host. She was very easy to contact with any questions and responded quickly to any concerns. Thank you for a great stay Kendra!"
Peaceful Seasonal lake front cottage with view of Burden 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
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1738)
"The staff was very nice! And the room was spacious and clean with plenty of amenities. "
The price is AED 620
AED 717 total
includes taxes & fees
2 Nov 2024 - 3 Nov 2024
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
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 AED 547
AED 600 total
includes taxes & fees
2 Nov 2024 - 3 Nov 2024
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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?
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