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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Cabin Rentals in Cheshire

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
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (11)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is NZ$275
includes taxes & fees
16 July - 17 July
Taborton Harvest Boulder Pines Cabin in the woods
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

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

9.8 out of 10, Exceptional, (28)
"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
Sun-loungers, beach towels

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!
2 bedrooms, iron/ironing board, Internet, bed sheets

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

9.0 out of 10, Wonderful, (30)
"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!
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, (11)
"Lovely location, charming property, great experience"
The price is NZ$493
includes taxes & fees
28 July - 29 July
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
Dadzpad Cabin in Stephentown
Fridge, microwave, oven, stovetop

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
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 NZ$734
includes taxes & fees
28 July - 29 July
Florida Mountain Log Cabin!
Breathtaking Mtn Views: Stylish Rustic Retreat!
2 bedrooms, desk, travel cot, free Internet

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!
Lakefront House with Stunning Views and Great Room
Dining

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
Taborton Harvest Timber Trails Unique cabin experience
Fridge, microwave, oven, stovetop

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 NZ$296
includes taxes & fees
30 July - 31 July
Taborton Harvest Timber Trails Unique cabin experience
Charming 3-bedroom Cabin for nature lovers
Interior

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...
The price is NZ$571
includes taxes & fees
16 July - 17 July
Charming 3-bedroom Cabin for nature lovers
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, (121)
"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
Bear Creek Cabin
Exterior

Bear Creek Cabin

10.0 out of 10, Exceptional, (32)
"Enjoyed our stay"
The price is NZ$996
includes taxes & fees
28 July - 29 July
Bear Creek Cabin
Berkshires Cabin 2 Mi to Appalachian Trail!
Dining

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!
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, (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
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)
"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
Crooked Lake Cabin
Smart TV

Crooked Lake Cabin

10.0 out of 10, Exceptional, (2)
"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
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."
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
TV

Cozy Stockbridge Cabin - Walk to Beach & Lake!

9.2 out of 10, Wonderful, (9)
"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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Frequently asked questions

What are the best cabins near Cheshire?
Stay in one of our 385 cabins in Cheshire and you'll be rewarded with beautiful scenery, outdoor adventure and memories to treasure. Log Cabin Living On The Esopus Creek is where life seems to slow down. Private And Artistic Cabin, Pet Friendly is another great choice if you're craving time out in Mother Nature.
Are there cheap cabins in Cheshire?
Whether you're eager to stay close to the water or in the hills, we've got a great variety of cheap cabins in Cheshire to suit your taste and budget. Priced from NZ$275 to NZ$996 per night, your perfect cabin is waiting here.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best mountain cabins near Cheshire?
If you're after crisp air and spectacular views, you can't beat a Cheshire mountain cabin. Explore the rugged beauty around The Luxury Lodge - Ski, Ride, Golf. This tourist favourite has everything you need for an unforgettable escape, including nearby hunting activities and a microwave oven. Or, enjoy a taste of the mountain lifestyle at Cabin - The Lakefront Retreat - Ski, Ride. It features a wood stove, nearby hunting activities and more.