Search the Best Cabins in Cheshire

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Our top choices for Cheshire cabin rentals

Exterior
Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
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."
United States
Georgia M.
$165 nightly
The price is $183
Dec 21 - Dec 22
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Exterior
Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers
Stephentown
7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
$262 nightly
The price is $291
Dec 21 - Dec 22
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers
Exterior detail
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (34)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
$395 nightly
The price is $441
Dec 21 - Dec 22
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
$165 nightly
The price is $183
Dec 21 - Dec 22
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Exterior
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Averill Park
10.0 out of 10, Exceptional, (3)
"Our family had a great weekend get-away at the Lake House! Thank you for the kind special touches, such as the milk and eggs from June Farm. The lake access and screened in porch were huge hits with everyone."
United States
Andrea N.
$1,004 nightly
The price is $1,114
Jan 1 - Jan 2, 2026
Total with taxes and fees
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Exterior
Bear Creek Cabin

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (43)
"We enjoyed our stay!!"
United States
Hillary S.
$539 nightly
The price is $602
Dec 21 - Dec 22
Total with taxes and fees
Bear Creek Cabin
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"My stay was great with no problems. "
scott 2-night trip
Posted 1 day ago
Vacation Village in the Berkshires

Find out more about Cheshire

Cheshire Cabin Rentals information

Number of reviews
92
Accommodation
26 Cabin Rentals
Lowest Price
$183
Highest Price
$1,114

Frequently asked questions

What are the best cabins near Cheshire?
Ranging from small and rustic to spacious and luxurious, there are 380 cabins on offer in and around Cheshire. Standouts include Log Cabin Living On The Esopus Creek and Private And Artistic Cabin, Pet Friendly.
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 $183 to $1,114 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 stunning views, it's hard to beat a Cheshire mountain cabin. Surround yourself in nature at Cabin - Hunter Lakefront House: Ski, Swim. This rental has all you need for an idyllic escape, including a microwave oven and a dishwasher. Alternatively, experience the mountain lifestyle at Cabin - Charming, Quiet, River Front. It offers snowsport activities, skiing facilities and more.
What are the best river cabins near Cheshire?
When you think of the word peaceful, a river cabin near Cheshire should jump to mind. Cabin - Charming, Quiet, River Front is one place where you can enjoy some calm. As well as its lovely surroundings, it comes with amenities such as snowsport activities and skiing facilities. Cabin - Romantic Retreat is another favorite. On-site watersports and snowsport activities are among the conveniences you'll have at hand here.
What are the best cabins with pools near Cheshire?
Hop into your swimsuit and splash around at your leisure when you reserve one of our cabin rentals with a pool near Cheshire. Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna is a top choice. A swimming pool and a porch are some of the other amenities you can take advantage of here. Alternatively, enjoy some time out at Cabin - Romantic Retreat. As well as a great pool, this cabin offers on-site watersports and a swimming pool.
Can I find beach cabins near Cheshire?
Wake up and wander down to the shoreline when you book a Cheshire beach cabin rental. Sunshine and fun should be your top priorities at Cozy Private Lake Cabin Minutes To Lake George And Saratoga Springs. This seaside retreat offers on-site watersports and beach sun loungers. Or, toss your bag down and cozy up at Cabin - Relax, Reconnect And Enjoy. Conveniences here include on-site watersports and children's activities.
What are the best weekend cabin rentals in Cheshire?
If you can't wait to spend two or so glorious days surrounded by nature, Cabin - Hunter Lakefront House: Ski, Swim will check all your boxes. Kick back here for a weekend and make use of conveniences including on-site watersports and a patio. Another popular retreat is Cabin - Charming, Quiet, River Front. Offering a patio, a firepit and plenty of chill vibes, you'll go home feeling like a new person.
What are the best cabin prices in Cheshire?
If you'd prefer to save some cash on your stay, Expedia has some fantastic offers on Cheshire cabins that won't put a dent in your vacation budget. How does $183 a night sound?
Can I find log cabins in Cheshire?
For many nature lovers, the perfect outdoor vacation just isn't complete without staying in a log cabin filled with character. Get exploring or simply unplug and unwind at Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. Activities such as skiing and hiking are just some of the fun things to do here. Another log cabin getaway is Luxury Secluded Catskill Log Cabin On Creek. Horse riding and snow shoeing will keep you active when you're not kicking back in your timber-clad digs.
What are the highest-rated cabins in Cheshire?
Expedia cabin travelers keep returning to Cabin - Artist's Camp On Lake Mahkeenac. This top-notch option comes with a host of useful amenities like a patio and a fireplace. It won't take you too long to understand why Cabin With 3 Acres, Tennis Courts: By 4 Ski Mtns is also a hit with travelers. Conveniences like a porch and a tennis court will help make your vacation the best one yet.
Why should I book a cabin in Cheshire?
For a vacation experience that's big on character, comfort and affordability, a cabin is the best choice. Lose your city blues in the greenery of the wilderness. From fun-filled days to cozy nights cuddled up with your special someone, cabins offer the perfect mix of excitement and relaxation. Check out all the great Cheshire options right here on Expedia.
What are the top nature cabins in Cheshire?
Unpack your bags at Cabin - Charming, Quiet, River Front and let your troubles drift away. Fun activities like nearby hiking and biking trails and nearby sledding help make this river cabin in Cheshire a top choice. Cabin - Romantic Retreat is another great place to hang out among nature. If you're in the mood for adventure, go nearby sledding and nearby motor boating.
What are some of the best cabins near National Shrine of the Divine Mercy in Cheshire?
Escape the hustle and bustle and journey into nature from a National Shrine of the Divine Mercy cabin. Get up close to wildlife, inhale the fresh air and then relax at Cozy Stockbridge Cabin - Walk To Beach And Lake. Fun activities such as nearby hiking and biking trails and nearby motor boating are just moments away here. Another place where you can relax and feel at home is Cabin - Artist's Camp On Lake Mahkeenac. Nearby motor boating and nearby kayaking are a few things to keep you busy during your visit.

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