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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 32 Cabin Rentals in Cheshire with updated reviews, rates, and availability.

Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (30)
"Loved it, will definitely book again!"
The price is AED 1,469
AED 2,150 total
includes taxes & fees
18 May - 19 May
Bear Creek Cabin
Charming 3-bedroom Cabin for nature lovers
Interior

Charming 3-bedroom Cabin for nature lovers

The price is AED 569
AED 1,174 total
includes taxes & fees
18 May - 19 May
Charming 3-bedroom Cabin for nature lovers
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, (24)
"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
Cabin in the woods
Exterior

Cabin in the woods

10.0 out of 10, Exceptional, (10)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is AED 441
AED 652 total
includes taxes & fees
16 May - 17 May
Cabin in the woods
Berkshires Cabin 2 Mi to Appalachian Trail!
TV, fireplace, books

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (11)
"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!
Vermont Lake Front Log Cabin Close to Mt. Snow
Exterior

Vermont Lake Front Log Cabin Close to Mt. Snow

10.0 out of 10, Exceptional, (66)
"What an incredible property, town and area. If you’re looking to get away for a bit in New England, it’d be hard to beat this place. Absolutely loved it, close to many small towns with great food and shops and views. Will be back again!!"
Vermont Lake Front Log Cabin Close to Mt. Snow
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
1 bedroom, in-room safe, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (8)
"Lovely location, charming property, great experience"
The price is AED 771
AED 1,195 total
includes taxes & fees
19 May - 20 May
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
Florida Mountain Log Cabin!
Living area

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Place was super clean. Beds were comfortable. Location was great."
The price is AED 1,451
AED 2,395 total
includes taxes & fees
16 May - 17 May
Florida Mountain Log Cabin!
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
2 bedrooms, iron/ironing board, internet, bed sheets

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

9.0 out of 10, Wonderful, (30)
"Charming decor and solid furniture. Lovely screened porch and deck. Micro kitchen—smaller that we expected but we’ll-equipped. Bedrooms also smaller than expected. Beds were good. "
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
A-Frame Cabin w/ Furnished Deck in Becket!
Exterior

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very Good, (7)
"We had a wonderful stay in this adorable a frame!! Super cozy :)"
A-Frame Cabin w/ Furnished Deck in Becket!
Taborton Harvest Timber Trails Unique cabin experience
Exterior

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."
The price is AED 441
AED 652 total
includes taxes & fees
16 May - 17 May
Taborton Harvest Timber Trails Unique cabin experience
Breathtaking Mtn Views: Stylish Rustic Retreat!
2 bedrooms, desk, travel crib, free internet

Breathtaking Mtn Views: Stylish Rustic Retreat!

10.0 out of 10, Exceptional, (27)
"Home was clean and well appointed. Gravel road and drive were better than expected and it was easy to get to town for sightseeing the battle monument, hiking and biking. We slept well and enjoyed the property."
Breathtaking Mtn Views: Stylish Rustic Retreat!
Lakefront House with Stunning Views and Great Room
Fridge, microwave, oven, stovetop

Lakefront House with Stunning Views and Great Room

9.6 out of 10, Exceptional, (15)
"Over all we loved this cabin. The outdoor spaces are wonderful. Dusk setting over the lake while sitting on deck with a drink was as close to perfection as you can get. We enjoyed kayaking around the lake. Very peaceful. The cabin is large. We used the fireplace every night. The only knock is the bugs and cobwebs in the high spaces. "
Lakefront House with Stunning Views and Great Room
Artist's Camp on Lake Mahkeenac
Property map

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
Dadzpad Cabin in Stephentown
Fridge, microwave, oven, stovetop

Dadzpad Cabin in Stephentown

8.0 out of 10, Very Good, (1)
"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
Modern Cabin Near Tanglewood
Property grounds

Modern Cabin Near Tanglewood

10.0 out of 10, Exceptional, (8)
"We had a great time staying in Lauren and Blake's cabin. It was very comfortable, clean and convenient and I would definitely stay there again. Thank you for being great hosts!"
Modern Cabin Near Tanglewood
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Exterior

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

9.8 out of 10, Exceptional, (56)
"This cabin was just perfect for our family vacation to the Berkshires. It was clean, had everything we needed, and Marlena was extremely helpful and responsive. We hope to be back some day!"
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Lakeshore cabin with private beach and dock
Exterior

Lakeshore cabin with private beach and dock

10.0 out of 10, Exceptional, (4)
"Took advantage of the peaceful setting and location to nearby attractions!"
Lakeshore cabin with private beach and dock
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
3 bedrooms, iron/ironing board, free WiFi, bed sheets

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

10.0 out of 10, Exceptional, (2)
"We had a wonderful family weekend at the lake house. Beautiful place to stay. Perfect for a family gathering."
The price is AED 1,488
AED 2,797 total
includes taxes & fees
19 May - 20 May
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
TV

Cozy Stockbridge Cabin - Walk to Beach & Lake!

9.4 out of 10, Exceptional, (8)
"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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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, (1804)
"The property was clean and the staff very accommodated."
The price is AED 434
AED 525 total
includes taxes & fees
18 May - 19 May
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, (929)
"Out dated not many resort like options "
The price is AED 488
AED 545 total
includes taxes & fees
16 May - 17 May
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.