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Vacation Homes in Cheshire

Our top choices for Cheshire vacation homes

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is AED 595
AED 1,440 total
includes taxes & fees
3 Sep - 4 Sep
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

10.0 out of 10, Exceptional, (12)
"Great property, plenty of space and room for all. Location is ideal"
The price is AED 859
AED 2,032 total
includes taxes & fees
30 Sep - 1 Oct
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is AED 1,273
AED 2,330 total
includes taxes & fees
10 Sep - 11 Sep
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (256)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is AED 551
AED 837 total
includes taxes & fees
16 Sep - 17 Sep
Berkshire Village Carriage House - Super Private!!

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is AED 837
AED 1,875 total
includes taxes & fees
1 Sep - 2 Sep
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.6 out of 10, Excellent, (32)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is AED 437
AED 1,076 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is AED 988
AED 1,822 total
includes taxes & fees
11 Sep - 12 Sep
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is AED 1,377
AED 1,859 total
includes taxes & fees
1 Sep - 2 Sep
Bungalow in the Berkshires

Two Brooks Lodge

3.0 star property
4.8 out of 10, (3)
"Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've...
Two Brooks Lodge

North Getaway Cottage

9.6 out of 10, Exceptional, (21)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is AED 744
AED 1,623 total
includes taxes & fees
4 Sep - 5 Sep
North Getaway Cottage

3-bedroom house in beautiful Berkshires, close to amenities!

The price is AED 755
AED 1,246 total
includes taxes & fees
3 Sep - 4 Sep
3-bedroom house in beautiful Berkshires, close to amenities!

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AED 591
AED 1,760 total
includes taxes & fees
1 Sep - 2 Sep
Comfortable Berkshires retreat on mtn resort, SISO

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (3)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is AED 749
AED 1,739 total
includes taxes & fees
1 Sep - 2 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,847 total
includes taxes & fees
2 Sep - 3 Sep
Hancock Village Inn at Jiminy Peak

Experience Timeless Elegance in The Edith Wharton Room!

The price is AED 762
AED 1,101 total
includes taxes & fees
8 Sep - 9 Sep
Experience Timeless Elegance in The Edith Wharton Room!

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is AED 735
AED 1,650 total
includes taxes & fees
1 Sep - 2 Sep
Near Tanglewood: Historic Summer Retreat

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

9.8 out of 10, Exceptional, (71)
"We had a wonderful stay, thank you! "
The price is AED 962
AED 2,023 total
includes taxes & fees
31 Aug - 1 Sep
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Cozy Carriage House room with a double bed and private balcony

The price is AED 879
AED 1,265 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Carriage House room with a double bed and private balcony

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
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