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Search the Best Cabins in Cheshire

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Cabin Rentals in Cheshire

Newly Renovated Cabin in the Country
Surrounded by lush greenery, this cabin-style building features a charming front porch and a stone chimney.

Newly Renovated Cabin in the Country

10.0 out of 10, Exceptional, (30)
"Very comfortable place with everything we needed for great week!"
Newly Renovated Cabin in the Country
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
$148 nightly
The price is $164
Aug 5 - Aug 6
Total includes taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Florida Mountain Log Cabin!
Cozy cabin-style accommodation with a wooden staircase, living area, dining table, and kitchen.

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Place was super clean. Beds were comfortable. Location was great."
$364 nightly
The price is $384
Aug 5 - Aug 6
Total includes taxes and fees
Florida Mountain Log Cabin!
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
Cozy bedroom with a rustic ceiling, a made bed featuring a bear design quilt, and a window with a view.

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

10.0 out of 10, Exceptional, (13)
"Lovely location, charming property, great experience"
$275 nightly
The price is $305
Aug 12 - Aug 13
Total includes taxes and fees
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Situated in a wooded area, this charming house features a front porch and a small garden with plants and a decorative pumpkin.

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

9.8 out of 10, Exceptional, (29)
"We had a great time in the cottage. It was perfectly cozy for our family of 6. The cottage has everything you need to have fun on a cold winter night. We especially enjoyed the hot tub and board games! Thanks for a lovely stay - we will come back in the summer!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Artist's Camp on Lake Mahkeenac
Enjoy serene lakeside views and peaceful surroundings, perfect for picnics and outdoor activities.

Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (19)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Relax in comfort with a large bed, flat-screen TV, and wooden dresser.

Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!

9.2 out of 10, Wonderful, (31)
"Adorable cabin with a central location to see everything in the Pioneer Valley/ Berkshires/Greater Springfield areas. The cabin is perfect for playing games, fishing, exploring the nearby lake and state parks or just plain relaxing! Be sure to bring marshmallows for toasting in the fire pit. Enjoy!"
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Dadzpad Cabin in Stephentown
Kitchen with central island, stove, microwave, and sink, featuring a window and patterned tile floor.

Dadzpad Cabin in Stephentown

5.0 out of 10, (2)
"House was clean and comfortably furnished. The kids enjoyed the arcade games and it was an overall good time. Only Issues were that the drive and walk ways were hidden in the snow and the house did not hold heat well "
Dadzpad Cabin in Stephentown
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Stylish log cabin with a central entrance and two windows on each side, set amidst a well-manicured lawn.

Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum

9.8 out of 10, Exceptional, (57)
"Great cabin on a beautiful lake. Scenic drive to all other attractions in the Berkshires (Lenox, Mt. Greylock, etc.). We enjoyed our stay!"
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Lakefront House with Stunning Views and Great Room
Enjoy meals at the large dining table surrounded by four chairs, with a serene lake view through the large windows.

Lakefront House with Stunning Views and Great Room

9.6 out of 10, Exceptional, (15)
"Beautiful setting. We had fun exploring the area and made good use of the kayaks to explore the lake."
Lakefront House with Stunning Views and Great Room
Breathtaking Mtn Views: Stylish Rustic Retreat!
Cozy cabin interior with a wooden staircase, comfortable seating area, and brick chimney.

Breathtaking Mtn Views: Stylish Rustic Retreat!

10.0 out of 10, Exceptional, (29)
"The pictures of this place do not even do it justice. It was breathtaking. We had so much fun exploring Bennington during the day and returning to Big Sky to relax and enjoy the beautiful property. The house had everything we needed and more; the beds were so comfortable, and we enjoyed our time together. We will be back soon!"
Breathtaking Mtn Views: Stylish Rustic Retreat!
Taborton Harvest Timber Trails Unique cabin experience
Enjoy cooking in this well-equipped kitchen with a central island, sink, and ample counter space.

Taborton Harvest Timber Trails 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."
$160 nightly
The price is $178
Aug 5 - Aug 6
Total includes taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Charming 3-bedroom Cabin for nature lovers
Cozy room with a stone fireplace, flat-screen TV, and patterned rug.

Charming 3-bedroom Cabin for nature lovers

8.0 out of 10, Very Good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
$305 nightly
The price is $339
Aug 10 - Aug 11
Total includes taxes and fees
Charming 3-bedroom Cabin for nature lovers
Bear Creek Cabin
Situated in a forested area, this cabin features a spacious porch, large windows, and a steeply pitched roof.

Bear Creek Cabin

10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
$539 nightly
The price is $602
Aug 11 - Aug 12
Total includes taxes and fees
Bear Creek Cabin
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Relax on the spacious deck with a covered seating area, surrounded by lush greenery.

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (122)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Berkshires Cabin 2 Mi to Appalachian Trail!
Enjoy meals around a large round table in a room with a window offering a view of the surrounding forest.

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (12)
"The cabin was pretty much all we could wish for to spend a few cozy days in the beautiful Berkshires! "
Berkshires Cabin 2 Mi to Appalachian Trail!
A-Frame Cabin w/ Furnished Deck in Becket!
Situated in a forested area, this cabin features a balcony for outdoor relaxation and a gravel pathway leading to the entrance.

A-Frame Cabin w/ Furnished Deck in Becket!

8.6 out of 10, Excellent, (8)
"We had a wonderful stay in this adorable a frame!! Super cozy :)"
A-Frame Cabin w/ Furnished Deck in Becket!
Crooked Lake Cabin
Cozy living room with a central fireplace, comfortable sofa, and rustic bench.

Crooked Lake Cabin

10.0 out of 10, Exceptional, (3)
"Very quiet very neat cottage on a small lake in Albany areaI would highly recommend this property.Lake view is beautiful with lots of windows to watch the water and boats working kitchen has new appliances, bathroom totally updated washer and dryer a big plus as well We felt relaxedas soon as we walked in"
Crooked Lake Cabin
Vermont Lake Front Log Cabin Close to Mt. Snow
Cozy cabin-style building with a spacious porch and wooden beams supporting the upper level.

Vermont Lake Front Log Cabin Close to Mt. Snow

10.0 out of 10, Exceptional, (67)
"The property was very nice, and the host was very accommodating and responsive. Would definitely stay here again. "
Vermont Lake Front Log Cabin Close to Mt. Snow
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Relax in this inviting living area with a sofa, armchair, and coffee table, featuring a gas stove and ample natural light.

Cozy Stockbridge Cabin - Walk to Beach & Lake!

9.4 out of 10, Exceptional, (11)
"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!
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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Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Great price for area with clean and spacious suites. Would be perfect if offered on site breakfast."
Barbara 1-night trip
Posted 1 day ago
Berkshire Mountain Lodge