Monthly Rentals in North Canaan

Very cute little place to stay and have a cozy weekend. Definitely recommend Campbell’s Falls (A hike John recommended to us)

Our stay at Rebecca's place was absolutely wonderful! The cozy, comfortable space provided the perfect home base for our Valentine’s weekend couple’s getaway. Located 35 min from Catamount (among other nearby ski mountains), the property offers a peaceful private setting while still being within easy reach of the slopes. Rebecca was an exceptional host. She provided fantastic local restaurant recommendations that really enhanced our experience. When it snowed on our departure day, she went above and beyond by arranging for the driveway to be plowed and even offered to extend our stay due to the weather. This kind of thoughtful consideration really made us feel cared for. The communication throughout our stay was gracious and prompt. Rebecca's attentiveness and hospitality truly made this a memorable stay. We would absolutely return and highly recommend this property to anyone looking for a comfortable, well-located rental with a host who goes the extra mile for her guests.

Great guest house in Sheffield. Absolutely beautiful setting and perfect location in Sheffield, close to Great Barrington. Karen was a great host in every way. Hope to return!

Another great stay! Sara has created an extremely comfortable and well-appointed home. Every time we thought of something we wanted or needed it was on a shelf or in a nearby cabinet. Great mattresses and comfy couches too!