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Compare 28 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, (4)
"Stayed for two nights enjoyed the nature and quietness. Was clean and owners had great communication."
The price is AED 441
AED 623 total
includes taxes & fees
24 Sep - 25 Sep
Cabin in the woods
Bear Creek Cabin
Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (18)
"Great cabin, modern, clean, and comfortable."
The price is AED 1,469
AED 2,211 total
includes taxes & fees
24 Sep - 25 Sep
Bear Creek Cabin
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, (61)
"From the very beginning everything went smoothly. Cabin is exceptional and being right on the lake is even better. We had an amazing time tucked away here."
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
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, (8)
"This is my second summer renting this house. It's great. Beautiful home, lots of light, in the woods, very comfortable. Our first year we had a rainy Sunday and it was fun to just hang out in. Very clean. The rental contact person was very responsive to a question we had. Five minutes from Jacob's Pillow. Lenox/Lee/Stockbridge are all just a quick drive away. Very quiet rural setting. A deer visited us this year, early on Sunday morning. Love this place."
Berkshires Cabin 2 Mi to Appalachian Trail!
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, (22)
"Three of us had a great stay! The cottage was very clean and very well outfitted. It was clear that the hosts put a lot of thought into making sure guests would have everything they need. The space is bright and modern but still cozy, very nicely designed. The lake was a bit more of a walk than I had imagined it would be and there isn’t much of a sitting area by the lakefront but the lake itself is beautiful. Overall, a very nice cottage and lovely stay!"
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
9.8 out of 10, Exceptional, (14)
"The house was nice and worked for our family. We were able to fish, kayak and swim. There was plenty of outdoor space to play games and spread out. There were plenty of outdoor chairs to use and beach towels as well. The kitchen was very well appointed with dishes and all the utensils that we needed. I was disappointed with the cleanliness. The kitchen sink was ceramic and was very stained and dirty. I cleaned it and it came out very well. The other item that should have been looked at before...
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, (33)
"We just spent four weeks at the Country Cabin. The cabin is charming. The hostess was very gracious. I appreciated her checking on us to make sure everything was satisfactory. The cabin is very cute, and accommodated our group of 4 very well. The basement room stayed cool, even without air conditioning. Loved the property, it was nice to walk around and fun to find a secret private entrance to the nature preserve. We appreciate the nice special touches. Did I mention hummingbirds? "
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, (28)
"We booked a couple nights to attend a show at Tanglewood and Chris and Ellen's Heartwood cabin did not disappoint. Great proximity to countless things of interest (amazing digital guidebook provided by hosts) we were only able to scratch the surface. So grateful dogs are able to enjoy the cabin and the gorgeous grounds. We will try to return down the road for sure!"
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!
8.4 out of 10, Very Good, (6)
"This A-frame cabin was the perfect location for some Berkshire R&R. Close to so many of western MA's greatest attractions, we had a great time visiting Tanglewood and museums, and touring local towns and restaurants. The property was clean, as described, and very comfortable. Communicating with our hosts was very simple. We will be happy to return!"
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, (7)
"We pulled in to a lighted log cabin that was lit by lights around the porch. You feel as if you are alone in the middle of the woods. It seemed all the restaurants were 20 minutes away. No shortage of good restaurants. We went to Tanglewood twice and what a treat. We saw Kool and the Gang and John Baptiste. Great performers playing in the Berkshires."
Berkshires Log Cabin by Evergreen Home
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!
Stylish Rustic Retreat w/ Breathtaking Mtn Views!
Bennington Vacation Rental | 2BR | 2BA | Stairs Required | 2,000 Sq Ft
Stylish Rustic Retreat w/ Breathtaking Mtn Views!
10.0 out of 10, Exceptional, (24)
"We absolutely loved this place! We stayed a week and miss it already. The views were outstanding. Honestly just sitting on the deck and doing nothing else would have been just fine. We were a range of ages, and everybody was happy. The house was incredible. The craftmanship was so unique and one of a kind. Had everything you need and the most comfortable beds! Would highly recommend this place. Joe and Corine couldn't of been more helpful. Looking forward to next year!"
Stylish Rustic Retreat w/ Breathtaking Mtn Views!
Artist's Camp on Lake Mahkeenac
Interior
Artist's Camp on Lake Mahkeenac
9.8 out of 10, Exceptional, (17)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac
Modern Cabin Near Tanglewood
Living area
Modern Cabin Near Tanglewood
10.0 out of 10, Exceptional, (8)
"A wonderful cabin with all the amenities you will need. Clean, beautifully decorated, and so much room. Highly recommend! Will be back for sure. "
Modern Cabin Near Tanglewood
Lakeshore cabin with private beach and dock
Exterior
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, (15)
"If you're looking to get away from the noise and bustle, but be close enough to some vibrant communities like Stockbridge and Lenox that have featured cultural offerings like music (Tanglewood) and theater (Shakespeare and Company), and spend your days in a modernized and pristine cabin with all the amenities, then this property is for you. Those were the features my wife and I were targeting. In addition, the owner was very responsive (a text away) when we had any questions. We recommend it...
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, (8)
"If you’re going to events at Tanglewood, this is a prime location. We added on an extra concert because of the easy 6 minute drive. This little lake cabin was quaint and cozy. The outdoor shower was superb. Would definitely stay here again! "
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 Pocumtuck Cabin @ The Wigwam Western Summit
Cozy Killarney Cabin
Room
Cozy Killarney Cabin
10.0 out of 10, Exceptional, (3)
"Lovely location, charming property, great experience"
The price is AED 826
AED 1,256 total
includes taxes & fees
30 Sep - 1 Oct
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.
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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, (1714)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is AED 620
AED 717 total
includes taxes & fees
24 Sep - 25 Sep
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (897)
"Was good everything "
The price is AED 537
AED 589 total
includes taxes & fees
26 Sep - 27 Sep
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (9)
"Near Jacob's Pillow!"
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.