Holiday houses in Winchester

Great place to visit! Walkable for restaurants in Wilmington and 10 minute drive to Mount Snow! Very affordable too.

A large, lovely, comfortable home, (comfy beds, plush, plentiful linens) in a great location! Loads of room for six adults, two kids and our pup. We want to make it a yearly event!

We were very happy with the space. The house was perfect; rooms beautiful, kitchen fully equipped, many bathrooms, hot tub was perfect for our group, and the game room was huge. We did some snow sledding in the area and a short hike, the area is beautiful. The hosts were responsive. We enjoyed our stay.

If you are looking for an idyllic lake house experience, this is it! We could have spent our entire trip just sitting on the porches—upstairs, downstairs, one screened-in porch, and the lovely dock. We used the kayaks and the paddle boat multiple times. The house was perfect for us because we are a close family of three, but if you need privacy from other guests, this wouldn’t be the ideal house as one bedroom opens into the other. The beds are soft and comfortable as is the sofa. Paula and Tim were extremely responsive and helpful. We would absolutely return to this house. It was difficult to leave the gorgeous leaves.

This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

I’m grateful that Peggy and Harry were willing to rent to us at the last minute. Our family needed a quiet respite to be together during a difficult time of loss. The solitude of the lake and woods was calming and we had plenty of room to be together. I only wish we could have stayed longer!

We highly recommend this house! Great space with everything we needed. The hot tub and fire place was a huge bonus. We had a 4W car and had no trouble driving through the back roads up to the house even during snow/sleet. Stephanie was fantastic- communicated well, helpful, accommodating and a pleasure to rent from.

We spent a few a nights here and loved our stay! The location is amazing -- easy car rides to nearby towns (hop on Route 2) and a short walk to Spring Street and the Willliams College campus. Our stay included some cold winter days, which made the ability to quickly walk to coffee shops and restaurants on Spring Street a plus. The home was super clean and welcoming and felt spacious for the 2 of us. Our impression was that William thought of everything -- e.g., when we wanted extra blankets (remember, we chose winter days for our visit :)), they were easy to find; when we wanted to run the dishwasher, the detergent was right there. We ended up baking a cake during our visit and found the kitchen remarkably well-stocked in terms of kitchen tools. From booking this place to heading out the door, we were extremely satisifed -- clear instructions, amazing location, lovely home. We feel lucky that we found this place and will be eager to return!

We had a lovely weekend in Megan’s home. The space was adequate for our family of 6. The home is in a quiet neighborhood that’s a short drive to Okemo so it was perfect for our ski weekend.