Holiday rentals 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!

Lucas’s home was perfect for a weekend getaway with a group of friends for a birthday celebration! Cozy and comfy sleeping spaces, great kitchen for cooking meals together, and perfect to stroll into town! Lucas was easily reached when a few minor questions came up and responded within minutes! Highly recommend!

This place was a breath of fresh air. I've noticed a trend on AirBNB of rentals that are obviously flipped investment properties with no character and no evidence of life: this place is the opposite! Charming, comfortable, with hosts who actually know the area and live in the area. This is a great family option when visiting the surrounding Hudson Valley towns. I hope I can get back here soon!

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!

Cannot thank Stephen enough for taking care of us after a major mess up. We were able to get in and relax and enjoy. So grateful for all he did for us on a graduation weekend.

This is our second time staying at Cindy’s beautiful place. It’s the perfect getaway and is extremely cozy, spacious and equipped with everything you need. We highly recommend staying here. Thank you Cindy!

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!

Our stay at the Sunset Bungalow was lovely. Rick sent excellent instructions and a full digital catalog of information about the place and surrounding area. It was clean, cozy, and warm...especially since we had a fire going most of the time we were there. The area is quiet and peaceful and it was easy to get into town for meals, shopping, etc. We stayed during a snow event and Rick was very gracious about letting us stay beyond the normal checkout time. He also had someone come by to shovel, salt, and make it easy for us to exit safely. He offered quick, friendly communication and we'd definitely stay again.

Great location and comfortable beds. We enjoyed having coffee next to the lake. Josh was very responsive when we had a question. All around great stay.