Holiday houses in Winchester

Shannon’s place was perfect for our Christmas visit with our son. Clean, spacious, great location, fully stocked, and made the perfect place to host our son and his Copper Mountain colleagues for Christmas!

Elizabeth is a phenomenal host, the place is one of the best I ever stayed in.. super clean, well stocked, (especially the kitchen made great impression) very clean.. An excellent value for the money… big and accommodating…

Excellent location with great parking in a well maintained condo. We had seven people and everyone felt really comfortable. We were able to cook a meal easily and watch a movie after skiing with the family. The rooms are the perfect size and the views are so peaceful. Only a four min drive to Stratton, so it made our weekend simple.

We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!

this was a last minute booking and everything was great. April was very efficient and responsive. no problems at all while we were there. Had snowfall the night we arrived , had to shovel out, that would have been nice to have a plow to plow the driveway, but we got out ok, but that was it. Between the 4 adults, we got it done for the most part. It was a very nice stay, thank you April.

Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.

Big group of friends and I stayed at Michele's place for a ski-weekend at Mount Snow. House was comfortable and fun with lots of games in the basement and space for us to hang out as a group in the main living area. Hot tub was 🧑‍🍳 perfection. Michele was responsive and helpful via messages.

⭐️⭐️⭐️⭐️⭐️ Amazing Stay with Wonderful Hosts! Our stay at Matt and Diane’s place was absolutely fantastic! From the very beginning, they were incredibly kind, welcoming, and helpful, ensuring we had everything we needed for a smooth and enjoyable visit. Their communication was excellent before, during, and even after our stay, making us feel truly taken care of. The property itself was exactly as advertised—spotlessly clean, well-equipped, and stocked with all the amenities we could ask for. It was the perfect place to relax and feel at home. Their attention to detail and hospitality made all the difference. I would highly recommend this property to anyone looking for a comfortable and stress-free stay. Thank you, Matt and Diane, for being such amazing hosts—we can’t wait to come back!