Photo by Ed Gaffny

Search Cabin Rentals in Cheshire

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Compare 25 Cabin Rentals in Cheshire with updated reviews, rates, and availability.

Cabin in the woods
Exterior
Cabin in the woods
10.0 out of 10, Exceptional, (2)
"Simple & comfortable. Good communication. "
The price is SAR 431
SAR 616 total
includes taxes & fees
29 Jun - 30 Jun
Cabin in the woods
Bear Creek Cabin
Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (14)
"Very well thought out rental home. Everything you could possibly need for cooking and all thought out to reduce your time cleaning and more time on the river. No issues and we had a great time. Thanks again,"
The price is SAR 1,501
SAR 2,275 total
includes taxes & fees
23 Jun - 24 Jun
Bear Creek Cabin
Berkshires Cabin 2 Mi to Appalachian Trail!
Otis Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | Stairs to Access
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
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Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Goshen Vacation Rental | 2BR | 1BA | 725 Sq Ft | Stairs Required for Access
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
9.0 out of 10, Wonderful, (28)
"This is a rustic, perfectly well outfitted cabin. Had everything that we needed in the kitchen. The beds and the couches were very comfortable. Bonus points for the well water being really soft and tasting good. It’s a sweet little spot. So grateful it is pet friendly!"
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, (18)
"Our stay at this cottage was wonderful. The property was perfect size for us and we enjoyed golfing at Bas Ridge Golf Course, even though the weather was not the greatest that day. The hot tub was such a great amenity and we enjoyed the nice quiet location!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Lakefront House with Stunning Views and Great Room
Property grounds
Lakefront House with Stunning Views and Great Room
10.0 out of 10, Exceptional, (12)
"Beautiful views from all the windows, quiet, private, clean and comfortable! Well worth a three day stay in October with all the leaves changing colors. Kayaks provided were so appreciated, allowing us to paddle around the whole lake and enjoy the colors and views even more. The downstairs bedroom and bathroom were ideal for my elderly mother. Great towns within easy drive, lots to explore!"
Lakefront House with Stunning Views and Great Room
Country Cabin- Nature preserve,Hiking, Skiing, fishing, swimming & pet friendly
Cozy Country Cabin
Country Cabin- Nature preserve,Hiking, Skiing, fishing, swimming & pet friendly
10.0 out of 10, Exceptional, (30)
"We love the yard and garden. The kitchen is perfect for light cooking away from home. The cleanliness is great!"
Country Cabin- Nature preserve,Hiking, Skiing, fishing, swimming & pet friendly
Newly Renovated Cabin in the Country
Exterior
Newly Renovated Cabin in the Country
10.0 out of 10, Exceptional, (26)
"Another great stay at this adorable cabin, and we even got to hear a pack of coyotes running by! Such a special place. We'll be back :)"
Newly Renovated Cabin in the Country
A-Frame Cabin in Becket: Deck + Private Acreage!
Becket Vacation Rental | 2BR | 1BA | Stairs Required | 1,100 Sq Ft
A-Frame Cabin in Becket: Deck + Private Acreage!
8.0 out of 10, Very Good, (4)
"What a beautiful property in a nice quiet location. We will be returning in the future"
A-Frame Cabin in Becket: Deck + Private Acreage!
Berkshires Log Cabin by Evergreen Home
Charming Log Cabin with wrap around porch!
Berkshires Log Cabin by Evergreen Home
10.0 out of 10, Exceptional, (6)
"Super clean, very comfortable, very nicely furnished as well as everything you could need to cook a gourmet meal. Pet friendly a bonus, and a nice quiet area with large yard for play with your furry kid. Loved that a question was immediately responded to. KUDOS to management. Highly recommend and would stay there again."
Berkshires Log Cabin by Evergreen Home
Vermont Lake Front Log Cabin Close to Mt. Snow
View from the lake
Vermont Lake Front Log Cabin Close to Mt. Snow
10.0 out of 10, Exceptional, (58)
"This place was magical! Great quiet location. The house had all the amenities you could ask for to stay comfortably. The host was great to communicate with and to make check in and check out smooth. Will be returning soon!"
Vermont Lake Front Log Cabin Close to Mt. Snow
Taborton Harvest Unique cabin experience
Exterior
Taborton Harvest Unique cabin experience
10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
Taborton Harvest Unique cabin experience
Bennington Cabin w/ Deck & Views of 3 States!
Bennington Vacation Rental | 2BR | 2BA | Stairs Required | 2,000 Sq Ft
Bennington Cabin w/ Deck & Views of 3 States!
10.0 out of 10, Exceptional, (22)
"The lodging, location and view exceeded our expectations. The owner was extremely helpful and responsive. We definitely want to return."
Bennington Cabin w/ Deck & Views of 3 States!
Artist's Camp on Lake Mahkeenac
Interior
Artist's Camp on Lake Mahkeenac
10.0 out of 10, Exceptional, (13)
"A most helpful owner made any bumps imperceptible. The area is a jewel and the cabin provides an excellent base for the Berkshires"
Artist's Camp on Lake Mahkeenac
Modern Cabin Near Tanglewood
Living area
Modern Cabin Near Tanglewood
10.0 out of 10, Exceptional, (2)
"This is a lovely cabin with a fire pit, surrounded by trees and yet close enough to walk into West Stockbridge. Hosts were prompt to reply to our messages and very helpful. One of the nicer properties we have stayed in!"
Modern Cabin Near Tanglewood
Lakeshore cabin with private beach and dock
Property grounds
Lakeshore cabin with private beach and dock
10.0 out of 10, Exceptional, (2)
"Took advantage of the peaceful setting and location to nearby attractions!"
Lakeshore cabin with private beach and dock
Fog Hill Cabin is a peaceful retreat set in a forest landscape. Stargazing Bliss
Exterior
Fog Hill Cabin is a peaceful retreat set in a forest landscape. Stargazing Bliss
10.0 out of 10, Exceptional, (10)
"We had a fabulous stay at the cabin for a long holiday weekend. The cabin was clean, warm, comfortable and had everything we needed. The holiday decor was so pretty especially driving back to the cabin at night and seeing it lit up with greens and white holiday lights. The coffee bar was an added bonus to wake up to. Billy responded quickly to my texts at check-in and check-out. There is much to do in this beautiful area and the cabin was centrally located for the places we wanted to visit...
Fog Hill Cabin is a peaceful retreat set in a forest landscape. Stargazing Bliss
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Stockbridge Vacation Rental | 2BR | 2BA | 700 Sq Ft | Stairs Required
Cozy Stockbridge Cabin - Walk to Beach & Lake!
9.4 out of 10, Exceptional, (6)
"Location of this property is near all things Stockbridge has to offer. Easy ride to Tanglewood Short ride to Lenox and Lee The cottage is an older gem Well stocked and lots of quirky charm"
Cozy Stockbridge Cabin - Walk to Beach & Lake!
The Pocumtuck Cabin @ The Wigwam Western Summit
Property grounds
The Pocumtuck Cabin @ The Wigwam Western Summit
10.0 out of 10, Exceptional, (1)
"My boyfriend and I stayed one night. The cabins were cozy and had a great view of the mountains. Lea is a wonderful host and provided us with complimentary coffee and tea. I would definitely go back again!"
The price is SAR 773
SAR 1,437 total
includes taxes & fees
22 Jul - 23 Jul
The Pocumtuck Cabin @ The Wigwam Western Summit
Cozy Killarney Cabin
Room
Cozy Killarney Cabin
10.0 out of 10, Exceptional, (2)
"This place is amazing ! Right on the lake ! Host was amazing ! Can’t say enough . It’s beautiful !!"
The price is SAR 1,032
SAR 1,493 total
includes taxes & fees
27 Jun - 28 Jun
Cozy Killarney Cabin
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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

Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (860)
"This is a sweet property. I visited in the summer. The dining options were great. The country store is awesome. I love how the rooms are suites. They feel like small apartments. I like that they have kitchens. The bed was comfortable. The ac is loud but at least it works well and it drowns out other noises. I needed a late check out and they were very cool about it. They let me hang out at the pool and then shower at the spa because I was like of stuck there several hours after check out time....
The price is SAR 596
SAR 654 total
includes taxes & fees
23 Jun - 24 Jun
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (8)
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
Peace and quiet on the lake
Exterior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (186)
"The house was clean and cozy. The kitchen was well stocked, especially important as we like to cook at home. Justin was responsive when I contacted him with questions. Love that the house was dog friendly with a fenced in back yard. The house has been updated inside but the deck needs some TLC, which I am sure are in the plans. A perfect get away!"
Peace and quiet on the 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.

Recent reviews of Cheshire hotels
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Loved the lake in the back !!!"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 2 days ago
The Black Swan Lee - Lenox, Ascend Hotel Collection