Photo by Ed Gaffny

Search Cabin Rentals in Cheshire

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 30 Cabin Rentals in Cheshire with updated reviews, rates, and availability.

Peaceful Mountain Cabin in the Berkshires
Aerial view

Peaceful Mountain Cabin in the Berkshires

The price is AED 408
AED 847 total
includes taxes & fees
3 Jun - 4 Jun
Peaceful Mountain Cabin in the Berkshires
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Exterior

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

10.0 out of 10, Exceptional, (116)
"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!
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!
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
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
Crooked Lake Cabin
Miscellaneous

Crooked Lake Cabin

Crooked Lake Cabin
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
30 May - 31 May
Bear Creek Cabin
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
30 May - 31 May
Cabin in the woods
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
30 May - 31 May
Taborton Harvest Timber Trails Unique cabin experience
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!
Charming 3-bedroom Cabin for nature lovers
Interior

Charming 3-bedroom Cabin for nature lovers

The price is AED 573
AED 1,186 total
includes taxes & fees
2 Jun - 3 Jun
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
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, (10)
"Lovely location, charming property, great experience"
The price is AED 771
AED 1,174 total
includes taxes & fees
9 Jun - 10 Jun
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
30 May - 31 May
Florida Mountain Log Cabin!
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!
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
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
Cozy Log Cabin on a private lake with incredible scenery.
Dining

Cozy Log Cabin on a private lake with incredible scenery.

10.0 out of 10, Exceptional, (4)
"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.
Newly Renovated Cabin in the Country
Exterior

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
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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free