Photo by Ed Gaffny

Search the Best Cabins in Cheshire

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Compare 25 Cabin Rentals in Cheshire with updated reviews, rates, and availability.

Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (13)
"Had such a wonderful stay in the beautiful Berkshires at this unique cabin property! Everything was clean and well-maintained. Very rustic and charming. We had a lot of fun by the fire and walking down to the river in the backyard. So many things to do in this area! Hiking, rafting, and dining in the nearby towns! Would definitely return!"
The price is $400
$602 total
includes taxes & fees
May 26 - May 27
Bear Creek Cabin
Exterior
Country Cabin- Nature preserve,Hiking, Skiing, fishing, swimming & pet friendly
10.0 out of 10, Exceptional, (28)
"The inside of the house was clean and very cozy! The kitchen was well equipped and the dart board in the basement was a fun touch! The outside of the cabin was well kept and secluded from neighbors. Steps away from the property was the nature preserve! We walked several of the trails and found a picnic table by the creek to stop and have lunch. The location of the cabin was perfect! We saw a concert in downtown Albany and it was roughly 30 minutes from the Cabin. This cabin was perfect for us as...
Country Cabin- Nature preserve,Hiking, Skiing, fishing, swimming & pet friendly
2 bedrooms, iron/ironing board, internet, bed sheets
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
9.0 out of 10, Wonderful, (28)
"This is a rustic, perfectly well outfitted cabin. Had everything that we needed in the kitchen. The beds and the couches were very comfortable. Bonus points for the well water being really soft and tasting good. It’s a sweet little spot. So grateful it is pet friendly!"
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
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Exterior
Lakeshore cabin with private beach and dock
10.0 out of 10, Exceptional, (2)
"Took advantage of the peaceful setting and location to nearby attractions!"
Lakeshore cabin with private beach and dock
Fridge, microwave, stovetop, coffee/tea maker
A-Frame Cabin in Becket: Deck + Private Acreage!
8.0 out of 10, Very Good, (4)
"What a beautiful property in a nice quiet location. We will be returning in the future"
A-Frame Cabin in Becket: Deck + Private Acreage!
Property grounds
Gorgeous Deck Views at this Serene Berkshires Cabin
8.8 out of 10, Excellent, (5)
"We had an amazing time at this spacious and well-equipped house! It provided everything we needed for a comfortable stay. The property's secluded location, nestled amidst breathtaking mountains and trees, created a truly serene and picturesque setting. Our family thoroughly enjoyed the peaceful surroundings. Additionally, the hosts were fantastic with their easy accessibility and great communication. We couldn't have asked for a better experience. Thank you, Michelle"
Gorgeous Deck Views at this Serene Berkshires Cabin
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, (18)
"Our stay at this cottage was wonderful. The property was perfect size for us and we enjoyed golfing at Bas Ridge Golf Course, even though the weather was not the greatest that day. The hot tub was such a great amenity and we enjoyed the nice quiet location!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Fridge, microwave, oven, stovetop
Lakefront House with Stunning Views and Great Room
10.0 out of 10, Exceptional, (12)
"Beautiful views from all the windows, quiet, private, clean and comfortable! Well worth a three day stay in October with all the leaves changing colors. Kayaks provided were so appreciated, allowing us to paddle around the whole lake and enjoy the colors and views even more. The downstairs bedroom and bathroom were ideal for my elderly mother. Great towns within easy drive, lots to explore!"
Lakefront House with Stunning Views and Great Room
Exterior
Newly Renovated Cabin in the Country
10.0 out of 10, Exceptional, (26)
"Another great stay at this adorable cabin, and we even got to hear a pack of coyotes running by! Such a special place. We'll be back :)"
Newly Renovated Cabin in the Country
Smart TV, fireplace, offices
Berkshires Log Cabin by Evergreen Home
10.0 out of 10, Exceptional, (6)
"Super clean, very comfortable, very nicely furnished as well as everything you could need to cook a gourmet meal. Pet friendly a bonus, and a nice quiet area with large yard for play with your furry kid. Loved that a question was immediately responded to. KUDOS to management. Highly recommend and would stay there again."
Berkshires Log Cabin by Evergreen Home
Exterior
Vermont Lake Front Log Cabin Close to Mt. Snow
10.0 out of 10, Exceptional, (58)
"This place was magical! Great quiet location. The house had all the amenities you could ask for to stay comfortably. The host was great to communicate with and to make check in and check out smooth. Will be returning soon!"
Vermont Lake Front Log Cabin Close to Mt. Snow
Interior
Bennington Cabin w/ Deck & Views of 3 States!
10.0 out of 10, Exceptional, (22)
"The lodging, location and view exceeded our expectations. The owner was extremely helpful and responsive. We definitely want to return."
Bennington Cabin w/ Deck & Views of 3 States!
Aerial view
Artist's Camp on Lake Mahkeenac
10.0 out of 10, Exceptional, (13)
"A most helpful owner made any bumps imperceptible. The area is a jewel and the cabin provides an excellent base for the Berkshires"
Artist's Camp on Lake Mahkeenac
Exterior
Modern Cabin Near Tanglewood
10.0 out of 10, Exceptional, (1)
"Our stay was fabulous!"
Modern Cabin Near Tanglewood
Exterior
Fog Hill Cabin is a peaceful retreat set in a forest landscape. Stargazing Bliss
10.0 out of 10, Exceptional, (10)
"We had a fabulous stay at the cabin for a long holiday weekend. The cabin was clean, warm, comfortable and had everything we needed. The holiday decor was so pretty especially driving back to the cabin at night and seeing it lit up with greens and white holiday lights. The coffee bar was an added bonus to wake up to. Billy responded quickly to my texts at check-in and check-out. There is much to do in this beautiful area and the cabin was centrally located for the places we wanted to visit...
Fog Hill Cabin is a peaceful retreat set in a forest landscape. Stargazing Bliss
Fridge, microwave, stovetop, dishwasher
Cozy Stockbridge Cabin - Walk to Beach & Lake!
9.4 out of 10, Exceptional, (6)
"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!
Property grounds
The Pocumtuck Cabin @ The Wigwam Western Summit
The price is $206
$383 total
includes taxes & fees
May 28 - May 29
The Pocumtuck Cabin @ The Wigwam Western Summit
1 bedroom, WiFi, bed sheets
Cozy Killarney Cabin
10.0 out of 10, Exceptional, (2)
"This place is amazing ! Right on the lake ! Host was amazing ! Can’t say enough . It’s beautiful !!"
The price is $275
$398 total
includes taxes & fees
May 27 - May 28
Cozy Killarney Cabin
View from property
Cozy Log Cabin on a private lake with incredible scenery.
10.0 out of 10, Exceptional, (2)
"A cozy lakefront cabin-nice and clean. The host was very responsive and went above and beyond with a few little extras for our crew. We loved being able to enjoy our morning coffee with a view of the lake. Our only wish was that the upstairs bathroom had a door. Would definitely stay here again!"
Cozy Log Cabin on a private lake with incredible scenery.
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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.

Other property types in Cheshire

Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (857)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is $154
$169 total
includes taxes & fees
Jun 5 - Jun 6
Jiminy Peak Mountain Resort
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the 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.

Cheshire Cabin Rentals information

Number of reviews
244
Accommodation
25 Cabin Rentals
Lowest Price
$206
Highest Price
$400

Frequently asked questions

What are the best cabins near Cheshire?
Ranging from quaint and compact to large and luxurious, you have 226 cabins available in and around Cheshire. Some great options include Cabin - Hunter Lakefront House: Ski, Swim and Windham 2 Bedroom Cabin In The Woods With Bonus Vintage Updated Camper.
Are there cheap cabins in Cheshire?
Priced between $206 and $400 a night, escaping the everyday is affordable and easy. Snap up one of our cheap cabins in Cheshire and enjoy plenty of outdoor fun without putting a dent in your budget.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’ve ever wanted to slip away to a cabin high in the mountains with only nature and epic views to keep you company, you’re definitely not alone. The Pocumtuck Cabin @ The Wigwam Western Summit is a magnet for guests craving some R&R. This mountain cabin near Cheshire offers many conveniences, such as nearby wildlife walks and nearby birdwatching activities. Also consider Mahican Cabin - A Private Natures Reserve For 2. A patio, a firepit and opportunities galore to get out into the wilderness make it a traveler favorite.
What are the best river cabins near Cheshire?
If you’re looking for a comfy hideout by the water, a Cheshire river cabin is a terrific choice. Recharge your batteries at Mahican Cabin - A Private Natures Reserve For 2 and let any worries float away downstream. Useful amenities here include a firepit and a queen bed. Another riverside getaway is Bear Creek Cabin. It offers a firepit, free firewood and more.
What are the best romantic cabins near Cheshire?
If you’re chasing somewhere to woo your partner, a romantic cabin rental is sure to impress. Cuddle up together at A Beautiful Log Cabin In The Woods. It features a fireplace, beach sun loungers and lots more. Bear Creek Cabin will also help you reignite your passion. Mountain views and a firepit are among the amenities to keep you both comfortable and content.
What are some great Cheshire cabins?
From plush pads with all the fancy perks to simple retreats that are easy on the hip pocket, Expedia has cabin rentals to suit every traveler. Spend a few days surrounded by Mother Nature at Cabin - Relax, Reconnect And Enjoy. Amenities here include a king bed and a water view. Another popular option is Beautiful Cozy Log Cabin With Hot Tub. It offers a fireplace, a barbecue grill and more.
What are the best weekend cabin rentals in Cheshire?
Whether you’re planning a quick break with your honey or the whole family, we’ll help you find your dream weekend cabin getaway. One of our favorites? Cabin - Relax, Reconnect And Enjoy. Featuring a fireplace and a firepit, you’ll adore the natural setting here. Beautiful Cozy Log Cabin With Hot Tub is another terrific place where you can hit pause on life. Book a few nights at this retreat which offers a fireplace and a barbecue grill.
What are the best cabin prices in Cheshire?
Whether you’re on a budget or want to treat yourself on your next vacation, you’ll find what you’re after with Expedia. At the moment, you can score a Cheshire cabin from just $206 a night.This price was 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.
Can I find log cabins in Cheshire?
If you’re craving a slower pace of life, you’ll discover it at one of our log cabins in Cheshire. For example, Beautiful Cozy Log Cabin With Hot Tub. Spend your days here going swimming and fishing and then return home to its rustic charms. You can also hit the brakes at Cozy And Bright Log Cabin Just 8 Minutes From Okemo Mountain. When you’re ready to venture beyond your cozy hideout, snowboarding and shore fishing opportunities are nearby.
What are the highest-rated cabins in Cheshire?
Guests just keep going back to Cabin - Relax, Reconnect And Enjoy. This superb option comes with lots of amenities including a fireplace and a firepit. It’s easy to figure out why Beautiful Cozy Log Cabin With Hot Tub is also a hit with visitors. Conveniences such as a fireplace and a barbecue grill will help make your vacation the best one yet.
Why should I book a cabin in Cheshire?
Affordability, nature-filled surroundings, rustic charm — there are lots of great reasons to stay in a Cheshire cabin. Get away from the loud and lively city and hear the sounds of birds and nature instead. There’s tons of adventure within striking distance too. Whether you’re taking a break with friends, relatives or your sweetie, you’ll find the perfect cabin on Expedia.
What are the top nature cabins in Cheshire?
The great outdoors won’t be the only thing you’ll be experiencing lots of while staying in a nature cabin in Cheshire. Adventure awaits around every corner too. Get cozy at Cabin - Beautiful Mt Area With Beautiful Scenic Views and find time for nearby snowboarding and nearby golfing. Another top rental is Cabin - Charming, Quiet, River Front. It’s known for its creature comforts on top of its nearby fishing and nearby motor boating opportunities nearby.

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Expedia verified reviews