
Vacation rentals in Cheshire
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Top-rated vacation rentals in Cheshire
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Top guest favorite

Home in Athens
5 out of 5 average rating, 38 reviewsPerfect home for a getaway from NYC
ScottRating, 5 stars3 weeks ago
Antonio and Yoon's place was perfect for our large group and dog. It's a very spacious home that is thoughtfully designed and in a lovely residential community. The beds and furniture were extremely comfortable, the backyard huge with a large patio and a fire pit. The six bedrooms, three full bathrooms, two living rooms, dining room, fully stocked kitchen, and finished basement gave our group of ten adults more than enough room to both gather together and enjoy time on our own. The location is near wonderful hikes and great restaurants and shops in Athens, Catskill, Hudson, and more. Antonio and Yoon were proactive, friendly, and clear in all communications. Highly recommended!
Top guest favorite

Home in Millerton
4.97 out of 5 average rating, 181 reviewsVacation Home In Millerton
SarahRating, 5 stars1 week ago
We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!
Guest favorite

Home in Monroe
4.93 out of 5 average rating, 14 reviewsThe Camp
BrendaRating, 5 stars2 months ago
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!
Guest favorite

Home in Bellows falls
5 out of 5 average rating, 8 reviewsAmazing Views, Skiing Nearby and Amenities Galore!
GillianRating, 5 stars2 months ago
We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!
Top guest favorite

Home in Great Barrington
5 out of 5 average rating, 13 reviewsGreat Barrington Ranch. Sleeps 10,Hot Tub, 5 acres
JuanRating, 5 stars1 month ago
We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!
Superhost

Home in Manchester
4.86 out of 5 average rating, 35 reviewsYour VT Dream House: Fireplace, Pool, Dogs
AtulRating, 5 stars8 months ago
Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.
Guest favorite

Home in Dover
4.89 out of 5 average rating, 71 reviewsLarge Mount Snow Ski House with Hot Tub
AndyRating, 5 stars1 month ago
Big group of friends and I stayed at Michele's place for a ski-weekend at Mount Snow. House was comfortable and fun with lots of games in the basement and space for us to hang out as a group in the main living area. Hot tub was 🧑🍳 perfection. Michele was responsive and helpful via messages.
Top guest favorite

Home in Athens
5 out of 5 average rating, 16 reviewsLake house with arcade games
AdrienneRating, 5 stars3 months ago
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.
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- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Magic Mountain Ski Resort
- Berkshire East Mountain Resort
- Saratoga Spa State Park
- Albany Center Gallery
- Saratoga Race Course
- Six Flags New England
- Taconic State Park
- John Boyd Thacher State Park
- Bousquet Mountain Ski Area
- Mount Sugarloaf State Reservation
- Mount Snow Ski Resort
- Otis Ridge
- Bash Bish Falls State Park
- Beartown State Forest
- Huck Finn’s Playland, Albany
- National Museum of Racing and Hall of Fame
- Canterbury Farm
- Naumkeag
- Stump Sprouts Ski Touring Center
- Berkshire Botanical Garden
- Hancock Shaker Village
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