Top Cottages in Cheshire County in 2025

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Compare 120 Cottages in Cheshire County with updated reviews, rates, and availability.

"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"

"This is a lovely cabin and the owners seem nice, but it needs a new cleaning plan. After arriving to a dirty microwave, dog food on the floor, a dirty floor, a moldy shower curtain, cobwebs over the table, etc… I did some digging on other sites to see people’s comments and they were the same. The owner’s response to them and to me was that it was professionally cleaned (if this is true, they need to be fired) and that he would talk to them. Well, nothing seems to have changed since the same...

Room, Private Bathroom (Spencer) | Living area | 28-inch flat-screen TV with satellite channels, TV, DVD player

"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "

"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."

"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."

"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"