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Browse Select Cheshire Holiday Homes

Our top choices for Cheshire holiday homes

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

includes taxes & fees

24 Sept - 25 Sept

3 bedrooms, iron/ironing board, WiFi, bed sheets

"as advertised."

includes taxes & fees

11 Sept - 12 Sept

"Great property, plenty of space and room for all. Location is ideal"

includes taxes & fees

16 Sept - 17 Sept

"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. "

includes taxes & fees

16 Sept - 17 Sept

"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "

includes taxes & fees

8 Sept - 9 Sept

includes taxes & fees

7 Sept - 8 Sept

"Very clean and spacious! We enjoyed our stay with our small pup!"

includes taxes & fees

18 Sept - 19 Sept

"Clean, nicely decorated, very well equipped home . We were 3 couples having a family reunion and attending a concert at Tanglewood. Comfortable beds. The wagon was very useful for our trip to Tanglewood. Would return again. Suggestions are to provide an umbrella for the deck- it was hot. Would have liked lawn chairs ( there was only 1) . Needs new decking. "

includes taxes & fees

7 Sept - 8 Sept

"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...