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Compare 54 Cottages in Cheshire with updated reviews, rates, and availability.

Property grounds
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (93)
"I had a wonderful time. The lil stone house school is restored in a loving way! It feels homie and cosy and has a lot of stories to tell. The location is great for seeing museums or just go for a hike. Rich and Cheryl are on top with everything and very nice hosts!"
Charming historic cottage on scenic road to Mt. Greylock
Property grounds
Cozy Cottage in the Woods
10.0 out of 10, Exceptional, (1)
"I have nothing but great things to say about our stay! Our hosts were great and very welcoming. The property was beautiful and our cottage as well. We will most definitely be back! Thank you!"
Cozy Cottage in the Woods
Outdoor pool
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (11)
"Very clean property with nice amenities near beautiful lake. Beds were comfortable owner very helpful with anything you might need"
Cozy cottage with pool, walking distance to lake
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Fridge, microwave, oven, stovetop
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
"the property was very well maintain, the host put alot of very personal and special touches inside the house.i have stayed in alot of houses over the years, but this one the host made you feel right at home."
Cozy Berkshire cottage with fireplace.
Beach nearby, sun loungers
Morgan House on Crooked Lake
10.0 out of 10, Exceptional, (6)
"Beautiful home on water. Perfect place to have family gatherings! Looking forward to another visit. Best area for pizza, too! ( Kay’s)"
Morgan House on Crooked Lake
Property grounds
Beachwood Cottage
10.0 out of 10, Exceptional, (1)
"Second time staying at the property. Comfortable, low key cabin. Access to private beach a big plus. Near Lenox, Stockbridge and Tanglewood."
Beachwood Cottage
Interior
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Interior
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
3.5 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Interior
Charlemont Retreat on Chickley River w/ EV Charger
3.5 star property
Charlemont Retreat on Chickley River w/ EV Charger
Property grounds
Cottage in the Clouds With Mountain Views
10.0 out of 10, Exceptional, (1)
"A sanctuary for writers and astronomers! Exquisite cottage and surroundings. Short hop to all that goes on in the Berkshires. You won't want to leave!"
Cottage in the Clouds With Mountain Views
Interior
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!
View from property
Picturesque Cottage with Sunroom on Ashmere Lake!
9.6 out of 10, Exceptional, (17)
"It was perfect for me and my close friends. We enjoyed the lake each day and all remarked that the beds were very comfortable. Wish we could have stayed longer."
Picturesque Cottage with Sunroom on Ashmere Lake!
Property grounds
Berkshires - Charming Lakefront Cottage
10.0 out of 10, Exceptional, (1)
"We stayed for a week at Stacy and Bob's place. Communication was excellent ahead of time. The house was incredibly clean upon arrival and everything was just as listed. They even went above and beyond with a wonderful welcome basket. They even had a small first aid/medicine kit, "just in case." We truly enjoyed their place."
Berkshires - Charming Lakefront Cottage
Interior
Family Winter Retreat w/ Hot Tub ~14 Mi to Slopes!
3.5 star property
Family Winter Retreat w/ Hot Tub ~14 Mi to Slopes!
Interior
Peaceful Family Home w/ Fire Pit & Large Yard
3.5 star property
Peaceful Family Home w/ Fire Pit & Large Yard
Exterior
Cozy Berkshires Cottage w/ 11 Private Acres!
Cozy Berkshires Cottage w/ 11 Private Acres!
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
Exterior
Black Bear Mountain Cottage
Black Bear Mountain Cottage
Interior
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
3.5 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
3.0 star property
Berkshires Cabin 2 Mi to Appalachian Trail!
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See all available properties in Cheshire
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.

Other property types in Cheshire

Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (857)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is $149
$163 total
includes taxes & fees
May 17 - May 18
Jiminy Peak Mountain Resort
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (183)
"We rented the house to celebrate mom’s 70th birthday. We wanted a quiet, simple place where we could spend time together, visit, and spend time outdoors. That’s exactly what we got. We all fished and kayaked and enjoyed the peaceful scenery. Thank you."
Peace and quiet on the lake
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
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.

Cheshire Cottages information

Number of reviews
138
Accommodation
54 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Cheshire cost?
Cottages in Cheshire range between and per night. These properties 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.
Why book your cottage in Cheshire with Expedia?
Expedia has some excellent cottages in Cheshire, so start packing for a memorable vacation close to nature. If you have a fixed budget, click on how much you’d like to spend and your preferred property star rating. Or, make your way to the filters to search for cottages with a hot tub or a kitchen. We’ll help you find the right place whatever your getaway looks like.
How can I find cheap cottages in Cheshire?
A wonderful way to uncover cheap cottages in Cheshire is with Expedia’s convenient filter tool. Narrow your search by star rating, amenities and budget to grab unbeatable prices in a few clicks.
What is there to do in Cheshire near my cottage?
You’ll find plenty of fantastic things that’ll fill up your itinerary in Cheshire. Drop by well-known attractions like Jiminy Peak Mountain Resort, Pittsfield State Forest and Berkshire Museum. Williamstown Theatre Festival, Colonial Theater and Barrington Stage Company are also visited by many.

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