Holiday houses in Winchester

We really enjoyed our stay at Sandi’s place. Each bedroom has its own bathroom, which is great for couples and families. The kitchen had everything we needed to cook a big NYE dinner. And it was just a few mins from Chatham center and I90, while still quiet and isolated. Sandi was great at communicating with us and was very flexible about check in and check out times, which we appreciated. We had one toddler with us and there was also a pack and play and a high chair. We would stay here again!

Our family had a great stay at Lucas’s house in Great Barrington. We were close enough to town to enjoy the amenities and also a short trip to butternut, where we had a great day of skiing with a group of mixed skiing experience. The house was comfortable and clean and we enjoyed the views from the big front windows.

We had a wonderful long weekend stay! Steve was an excellent host, who was very hospitable and responsive, allowing us flexible check in and check out, leaving a thoughtful welcome gift and sending us recommendations for things to do in the local area. We ended up hiking, wine tasting, visiting local restaurants. The home was great for our two kids (12 year old and 3 year old) and we made use of the pool every day! Wish we could've stayed longer but it was the perfect city getaway.

This was our best stay ever. Aline is very helpful & responds right away The scenery all around is magnificent & neighborhood is super peaceful. House is fully stocked with everything you might need during your stay We will definitely be back in the summer!

a beautiful stay for sure, very peaceful and removed from the city. My girlfriend and I will be staying there again for sure

Plenty of space for two families to share and wonderful for kids. Location is ideal for skiing and tubing plus town has good food and shops.

The sunset bungalow was a true gem. The items supplied in the kitchen went behind even the description, and left us wanting for nothing. The trail maps were so helpful and our family really enjoyed the blue trail. My sons are already asking to return this fall to see the foliage. 10/10 would stay again.

We thoroughly enjoyed our stay in Sally’s cozy apartment! It is well appointed and tastefully decorated. Sally was very responsive and caring. The beautiful views out of our bedrooms onto the garden and the wide open landscape behind it were major treats, especially on the morning after a heavy snowfall. We found everything we needed and more than expected - and hope to be back one day! Thank you very much, Sally!

My family had a wonderful stay at Carol‘s house! We were traveling with our two-year-old son and four-year-old daughter and this was the first time the kids saw snow! Carol was very helpful and responsive and even went out of her way to make sure the kids had some extra toys stocked at the house. The views are stunning and the house was well stocked (for the winter cold) with blankets, extra pillows, etc. We will be back to stay again!