Holiday houses in Winchester

We could not have found a better place to stay while having renovations done at our own home. We packed up our gaggle of golden retrievers and one beagle and felt welcomed the moment we stepped into the house. There were treats for the dogs, blankets to put on the couch, verrrry comfortable twin-sized memory foam dog beds and endless amounts of toys for our pups to enjoy. There was also a treat station as well as lickit mats and doggie painting to keep these retrievers happy and busy. This house is so dog friendly. It’s a perfect balance of a beautiful home for the humans that is also perfect for the dogs. The furniture was comfortable, the kitchen large and well-stocked with necessities, such as paper towels, dish soap, dishes, pots and pans and that stove…. Beautiful! The bed was very comfortable and cozy. If the dogs hadn’t wanted to get up so early, we may have slept part of the day away. Having the availability to do laundry was also very helpful. We truly enjoyed our stay!

Perfect place to stay for a ski weekend with two families. Easy walk (even for the kids) to the chair lift, able to ski back in all the way to the front steps, easy to go back for lunch in the middle of the day. Hot tub was great with heated mats on the deck. Had everything we needed. Beds super comfy. Plenty of space.

Place is going thru renovation so we got to our second floor apartment via steep and narrow stairs which could a problem for someone. Three spacious bedrooms and very clean and spacious bathroom. We absolutely loved the place.

This place was cozy and warm, the house was clean and spacious for a one bedroom. The shower had great water pressure and the kitchen was stocked with all the supplies you would need. Nina was accommodating and very sweet. Certainly would recommend for anyone to stay and we can’t wait to come back ourselves!!

A GREAT stay! We had a family weekend away here, the place was big enough to fit all of us with plenty of space. There is a TON of space in this home with large rooms! The great room has a beautiful view of the scenery, kitchen is well stocked with the essentials, and garage was great to keep ski gear in while we were not at the mountain. Would highly recommend staying here and our family would love to return!

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.

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 had a great stay at William and Mariachu's apartment. Everything was as seen in the photos. It is a very comfortable apartment with a spotless kitchen and bathroom and is close to everything in town. We'll stay again! Thank you!

Todd was so great to work with. Extremely responsive and helpful! His place was so cute, very clean and very well appointed. It has everything you could ever need and very organized. We rented it to ski at Wachusetts and it was great location( only 15 mins away). We would rent again. Thank you!