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Featured Cabin Rentals in Cheshire and around

Vermont Lake Front Log Cabin Close to Mt. Snow

10.0 out of 10, Exceptional, (64)
"I can’t say enough about our host, Bob, and this property. If you’re looking for a peaceful slice of heaven, this immaculate log cabin is the place. This is the cleanest rental we’ve ever stayed in and the attention to detail was incredible. The kitchen was super stocked and the furniture was comfortable, we immediately felt at home. The Firepit by the water was so relaxing and the fireplace inside was great to end the day. Thanks to Bob for the wood. Bob was extremely responsive and friendly,...
Vermont Lake Front Log Cabin Close to Mt. Snow

Cabin in the woods

10.0 out of 10, Exceptional, (9)
"This place was awesome... I was 15 minutes away working late... and I was too tired to drive home... I actually scheduled the wrong night and realized it after I got confirmation. But I messaged the renters and they just happened to have a cabin vacancy... they gave me the directions.. the key code and we worked everything out afterwards. The set-up is genius... the common area building has all the plumbing in it. Bathroom and showers with an open very well built living room with a kitchen. My...
The price is €167
includes taxes & fees
21 Feb - 22 Feb
Cabin in the woods

Bear Creek Cabin

9.8 out of 10, Exceptional, (25)
"Loved it, will definitely book again!"
The price is €581
includes taxes & fees
23 Feb - 24 Feb
Bear Creek Cabin

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (11)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!

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 €167
includes taxes & fees
21 Feb - 22 Feb
Taborton Harvest Timber Trails Unique cabin experience

Berkshires Log Cabin by Evergreen Home

10.0 out of 10, Exceptional, (7)
"We pulled in to a lighted log cabin that was lit by lights around the porch. You feel as if you are alone in the middle of the woods. It seemed all the restaurants were 20 minutes away. No shortage of good restaurants. We went to Tanglewood twice and what a treat. We saw Kool and the Gang and John Baptiste. Great performers playing in the Berkshires."
Berkshires Log Cabin by Evergreen Home

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

Breathtaking Mtn Views: Stylish Rustic Retreat!

10.0 out of 10, Exceptional, (26)
"We recently spent the holidays at Big Sky Cabin, and it was a fantastic experience from start to finish. Unlike the typical cabin kits found in artificial forests and tourist traps on zero lot line properties, Big Sky Cabin was legit a genuine solitude and an authentic mountain vaca.The amenities were rustic yet incredibly plentiful, providing everything we needed for a comfortable stay while maintaining the charm of a true cabin experience. The owners were exceptional—always available and even...
Breathtaking Mtn Views: Stylish Rustic Retreat!

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

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very good, (6)
"This A-frame cabin was the perfect location for some Berkshire R&R. Close to so many of western MA's greatest attractions, we had a great time visiting Tanglewood and museums, and touring local towns and restaurants. The property was clean, as described, and very comfortable. Communicating with our hosts was very simple. We will be happy to return!"
A-Frame Cabin w/ Furnished Deck in Becket!

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

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

9.0 out of 10, Wonderful, (30)
"This Pet-Friendly Cabin was very cozy. It is in a woodland neighbor of cabins, but it feels very secluded. Nobody was at the one cabin that we could see. The weather was cool while we were there, so we enjoyed a campfire outside and one in the indoor fireplace. The cabin was decorated by someone like my grandma who was obsessed with bears and apples. The cabin is a short stroll from a lake with a beach. Although our overall experience was good, there are few negatives. First, there are no...
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!

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

10.0 out of 10, Exceptional, (8)
"Kelly was a great host. Looking to come back in the summer for sure!"
The price is €309
includes taxes & fees
22 Feb - 23 Feb
Cozy Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !

Modern Cabin Near Tanglewood

10.0 out of 10, Exceptional, (8)
"A wonderful cabin with all the amenities you will need. Clean, beautifully decorated, and so much room. Highly recommend! Will be back for sure. "
Modern Cabin Near Tanglewood

Lakeshore cabin with private beach and dock

10.0 out of 10, Exceptional, (3)
"We love this place! It is conveniently located for Tanglewood and the Rockwell museum, quiet and secluded. The cabin and grounds show much care and attention by thoughtful owners. "
Lakeshore cabin with private beach and dock

Newly Renovated Cabin in the Country

10.0 out of 10, Exceptional, (29)
"We booked this escape as a 1/2 way point between family in NJ and MA and what a hidden gem it is! Dog friendly was a priority, but the magic of this place was a welcomed surprise. All weekend we commented on wishing we stayed longer and that we must come back to really enjoy the property and cozy feel that warms the soul! The cabin is meticulously maintained and it is very clear that the family loves their home away from home! Can’t wait to return!!"
Newly Renovated Cabin in the Country

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

Den Outdoors Cabin With STUNNING Adirondack Views - EV charging available

2.0 star property
10.0 out of 10, Exceptional, (1)
"Wow - from the great looking property, the well appointed amenities, and a sunset that will keep you captivated, we had a lovely experience! The house had everything for a convenient and comfortable stay, along with a lot of character that made every day special. Great communication with the host helped us feel at home. The thoughtful preparation of a ready fire in the hot tub was a nice touch! Thanks, Matthew, for a great stay. "
Den Outdoors Cabin With STUNNING Adirondack Views - EV charging available

Cozy Stockbridge Cabin - Walk to Beach & Lake!

9.4 out of 10, Exceptional, (8)
"If you’re going to events at Tanglewood, this is a prime location. We added on an extra concert because of the easy 6 minute drive. This little lake cabin was quaint and cozy. The outdoor shower was superb. Would definitely stay here again! "
Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cozy Log Cabin on a private lake with incredible scenery.

10.0 out of 10, Exceptional, (3)
"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.
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

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (84)
"This old barn was renovated into a great place to stay. Jane and Ian paid careful attention to details, light, colors, materials. Very comfortable and relaxing. The setting is gorgeous, and the sheep are fun. (FYI: It may be helpful to understand the layout and bathrooms: the new bathroom is at the far end of the smaller bedroom. This works great for a couple to have their own bathroom. The other bathroom is within the larger bedroom with the bunk bed, but in an area close to the door,...
19th c. Barn in the Berkshires

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1764)
"Great staff nice units great amenities "
The price is €124
includes taxes & fees
3 Mar - 4 Mar
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"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.

Frequently asked questions

What are the best cabins near Cheshire?
Immerse yourself in the outdoors without giving up the comforts at one of our 368 cabins in and around Cheshire. Whether you have relaxation or adventure on your mind, Log Cabin Living On The Esopus Creek promises both. Alternatively, book Private And Artistic Cabin, Pet Friendly and kick back among beautiful surroundings.
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 €167 to €581 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 need a fill of crisp air and stunning views, you can’t beat a Cheshire mountain cabin. Experience nature without roughing it at Hunter Lakefront House: Ski, Swim, Boat, Fish, Hike, Fire pit & Dog Friendly. This visitor favourite has all you need for an unforgettable escape, including a microwave oven and a dishwasher. Or, experience the mountain lifestyle at Cabin - Charming, Quiet, River Front. It features nearby wildlife walks, snowsport activities and more.
What are the best river cabins near Cheshire?
If you’re searching for a character-filled retreat moments from the water, a Cheshire river cabin is calling your name. Unpack your bags at Cabin - Charming, Quiet, River Front and let any stresses vanish downstream. Amenities here include nearby wildlife walks and snowsport activities. Another quality riverside stay is Cabin - Romantic Lake Retreat. Its conveniences include on-site watersports, nearby wildlife walks and more.
What are the best cabins with pools near Cheshire?
Slip on your bikini or board shorts and enjoy a refreshing dip whenever the mood strikes when you select one of our cabin rentals with a pool near Cheshire. Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna ranks high among travellers. A swimming pool and a porch are some of the other amenities you can take advantage of here. Or, catch up on some “me time” at Cabin - Romantic Lake Retreat. As well as a great pool, this cabin offers on-site watersports and a swimming pool.
Can I find beach cabins near Cheshire?
Get a big dose of sun and sea air at Cosy Private Lake Cabin Minutes To Lake George And Saratoga Springs. One of our leading Cheshire beach cabins, it offers guests on-site watersports and beach sun loungers. You can also spend lazy days by the shore at Relax, reconnect and enjoy!. On-site watersports and children’s activities will help make your break extra special.
What are the best weekend cabin rentals in Cheshire?
Nothing’s more relaxing than a weekend cabin getaway after an exhausting week at work. Swap your cramped office for two or three days in nature at Waterfront Cabin w/ private dock close to Saratoga & Lake George. On-site watersports and a patio are some conveniences it comes with. You can also forget all about work at Birch Hill Hollow - Mt Snow & pool table. Kick back here and make use of a spa tub and a patio.
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 holiday budget. How does €167 a night sound?
Can I find log cabins in Cheshire?
If you want a retreat that’s both relaxing and rugged, you can’t go past a log cabin rental. Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna is a popular choice that comes with loads of useful amenities, including a swimming pool and a porch. Another quality log cabin getaway is Luxury Secluded Catskill Log Cabin On Creek. Fusing rustic character with the comforts you need, it offers a porch, a firepit and more.
What are the highest-rated cabins in Cheshire?
Expedia adventurers just keep going back to Artist’s Camp on Lake Mahkeenac. This knockout comes with plenty of amenities including a patio and a fireplace. It’s easy to figure out why Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns is also a hit with holiday makers. Conveniences like a porch and tennis help make it a winner.
Why should I book a cabin in Cheshire?
For a holiday 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 cosy 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?
Escape to Waterfront Cabin w/ private dock close to Saratoga & Lake George and let life’s pressures float away downstream. Fun activities like nearby golfing and hiking help make this river cabin in Cheshire a popular pick. Charming, Quiet, River Front is another property where you can hang out in nature. If it’s adventure you’re seeking here, go nearby hiking and biking trails and hiking.