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Compare 26 Cabin Rentals in Cheshire with updated reviews, rates, and availability.

Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (20)
"The home was beautiful and we enjoyed our stay! The only thing about the location, it’s very remote. We had an event in North Adams and had a nearly impossible time getting a ride share service or taxi to come pick us up. Other than that, a wonderful stay!"
The price is SAR 1,502
SAR 2,260 total
includes taxes & fees
25 Nov - 26 Nov
Bear Creek Cabin
Cabin in the woods
Exterior

Cabin in the woods

10.0 out of 10, Exceptional, (8)
"Beautiful place with all amenities we needed."
The price is SAR 451
SAR 637 total
includes taxes & fees
1 Dec - 2 Dec
Cabin in the woods
A-Frame Cabin w/ Furnished Deck in Becket!
Becket Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Stairs Required to Enter

A-Frame Cabin w/ Furnished Deck in Becket!

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 w/ Furnished Deck in Becket!
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, (64)
"I can’t say enough about our host, Bob, and this property. If you’re looking for a peaceful slice of heaven, this immaculate log cabin is the place. This is the cleanest rental we’ve ever stayed in and the attention to detail was incredible. The kitchen was super stocked and the furniture was comfortable, we immediately felt at home. The Firepit by the water was so relaxing and the fireplace inside was great to end the day. Thanks to Bob for the wood. Bob was extremely responsive and friendly,...
Vermont Lake Front Log Cabin Close to Mt. Snow
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, (9)
"Enjoyed the foliage and some nice hikes. House was comfortable and clean. Owner was responsive and helpful. We arrived at night and had trouble locating the property when our gps failed. Owner was helpful guiding us to the house. I suggest arriving in the light of day. "
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, (23)
"My partner and I really enjoyed our relaxing stay at this quaint cottage. It was clean, comfortable, and tucked away in a very quiet area. It was easy to get to restaurants and theaters in Pittsfield / Lenox / Stockbridge. The hot tub was also a great way to spend a cozy fall afternoon!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Lakefront House with Stunning Views and Great Room
Terrace/patio

Lakefront House with Stunning Views and Great Room

9.6 out of 10, Exceptional, (15)
"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
Exterior

Country Cabin- Nature preserve,Hiking, Skiing, fishing, swimming & pet friendly

10.0 out of 10, Exceptional, (34)
"My friends and I stayed here, and we very much enjoyed a quiet place to stay at the end of the day. We were racing nearby at the Dragway for a few days, the location was great. The deer that visited in the yard was a nice touch. It's also a nice place to take in the sunrise from the deck with a coffee or two. We would definitely stay here again."
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
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, (30)
"This Pet-Friendly Cabin was very cozy. It is in a woodland neighbor of cabins, but it feels very secluded. Nobody was at the one cabin that we could see. The weather was cool while we were there, so we enjoyed a campfire outside and one in the indoor fireplace. The cabin was decorated by someone like my grandma who was obsessed with bears and apples. The cabin is a short stroll from a lake with a beach. Although our overall experience was good, there are few negatives. First, there are no...
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, (25)
"My husband and I stayed here with our two dogs for 3 nights. The location is incredibly beautiful, peaceful and quiet. And the view is stunning. We had a great time exploring the incredible acreage. Based on the exact address, it took a bit longer to get into town than we thought. We ate out for all our meals, so it took a bit of coordinating to try and get everything we needed for the day to minimize the back and forth. The house was great, very spacious. Everything was nice and clean. A couple...
Stylish Rustic Retreat w/ Breathtaking Mtn Views!
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
Artist's Camp on Lake Mahkeenac
Interior

Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (18)
"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
Property grounds

Lakeshore cabin with private beach and dock

10.0 out of 10, Exceptional, (3)
"We love this place! It is conveniently located for Tanglewood and the Rockwell museum, quiet and secluded. The cabin and grounds show much care and attention by thoughtful owners. "
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!
Cozy Killarney Cabin sits Directly on Crooked Lake- Scenic Views Galore !
Room

Cozy Killarney Cabin sits Directly on Crooked Lake- Scenic Views Galore !

10.0 out of 10, Exceptional, (5)
"Will be back!"
The price is SAR 751
SAR 1,171 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Killarney Cabin sits Directly on Crooked Lake- Scenic Views Galore !
Cozy Log Cabin on a private lake with incredible scenery.
Exterior

Cozy Log Cabin on a private lake with incredible scenery.

10.0 out of 10, Exceptional, (3)
"My husband turned 70, and as we have family in the area I decided to rent this beautiful property as a gathering place. It was beyond our expectations. We all have such wonderful memories."
Cozy Log Cabin on a private lake with incredible scenery.
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, (1746)
"Property was beautiful, great staff "
The price is SAR 634
SAR 733 total
includes taxes & fees
26 Nov - 27 Nov
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, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is SAR 559
SAR 614 total
includes taxes & fees
26 Nov - 27 Nov
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.