Cottage holiday rentals in Windsor County

I would definitely recommend this Airbnb. Plenty of space for our group and very responsive host. Location is close to Killington mountain/town.

There are not enough words to capture our experience staying at the Sun Cottage! From the moment we arrived we were amazed at the beauty of the lanscape and the cottage. The wealth of amenities and luxury of the cottage was astounding. We kept finding carefully placed unique touches throughout the cottage. Mornings spent on the patio eating breakfast and evenings in the hot tub listening to the sound of the brook nearby are just a few of the moments we cherished. Access to the pond abudding the property to swim as well as the trails along the brook made this an exceptioal getaway! Can't thank Hunter and Jess enough.

The pictures don’t even come close to capturing how amazing this place is! The whole home feels so warm and inviting—even better in person. We absolutely love how spacious and spotless it is. The host is super responsive, and the location is perfect—just a short drive to Killington Resort or Okemo. We had such a great stay that we’re already planning to book again for our next trip!

This was absolutely the best Airbnb I’ve ever stayed in! The cabin, the property, the scenery, absolutely beautiful! Would recommend to anyone for a nice relaxing peaceful vacation. In my experience with Airbnb Matt was the absolute most responsive, most proactive, and the most helpful host I’ve ever stayed with. During our stay we got hit with a massive snow storm, dumping around 16 inches of snow and before we even woke up the next morning everything was plowed and ready to go! Also, during our stay there was an issue with the hot tub and we weren’t able to use it but like I said Matt was extremely proactive and helpful through the situation and it didn’t hinder our stay at all. With all that being said this was absolutely the best Airbnb I’ve ever stayed at! Thanks again for everything Matt!

Always a pleasure to stay at Hope’s place. Feels like home away from home.

We stayed at the Shattuck Hill Cottage for a ski vacation. Sandra was a great host! Close enough to the mountain to get there everyday, but far enough away to avoid the tourist congestion. The cottage was comfy and cozy and we love that we can bring our doggo. Looking forward to our next stay!

Cozy and comfortable place! Bedrooms were all spacious and the common areas were great for spending time together when we were resting in the evenings. Close proximity to multiple ski resorts, and good restaurants within a 15 minute drive. Loved the charm of the home and imagine its great for stays year round.

The Mendon Cottage is clean, cozy and private. It’s just a 15 minute drive to Killington base, even in a fairly decent snow storm. There are trails behind the property that offered some good hiking for our doggo (they’re made for snowmobiles, but we didn’t spot one during our stay). The property delivers on its main promise: a less pricey alternative to staying at Killington, with very little inconvenience for the ski bums. Unless you simply can’t live without the ability to take the shuttle and ski off the mountain to your rental, you really can’t go wrong with this property. (It snowed our entire stay and the private road and driveway were plowed repeatedly and always navigable.)

The surroundings were beautiful and we loved watching the sun set over the mountains. The cottage was very clean and we really appreciated how well set up the kitchen was. Ron was friendly and responsive. We enjoyed finding swimming spots, local hikes and maple ice cream. We highly recommend the cottage and hope to return someday!

An absolutely wonderful place, and Rimma was very accommodating and communicative. My wife and I and our dog were there for three days, and actually were enjoying ourselves so much we almost accidentally stayed a fourth; we seriously forgot when we were leaving, and in dozens of AirBnB stays that's the first time that has happened. Would absolutely recommend and stay there again.

Charming Vermont home in beautiful Woodstock! Perfect for our weekend ski trip to Killington. Would stay again!

Stayed at Nicole’s cottage for a long ski weekend with my wife and pup. Exactly what we were looking for in regards to a private, clean, secluded getaway for a few days. She had the heat turned up (gas fireplace) which was welcoming for our arrival in the cold. Nicole was great in touching base before and during the stay making sure everything was in order. She also shared tips on local shops/eateries making it easy to prearrange. Good proximity to slopes. Will look to stay again in the future.

Wonderful stay. Place had everything we needed and a great location close by to Bromley, Magic and Okemo. Would stay again at Moonbeam.

We just got back from an amazing few days at Breezy Pines. Mary was always quick to respond to any questions I had. The cottage was well equipped from kitchen supplies to comfortable linens and towel, Wi-fi, as well as wood for the fire pit. We enjoyed lazy days lounging in the sun and swimming. Meals were enjoyed on the screen porch overlooking the lake. Amazing sunset views. We enjoyed every minute of our stay.

We felt right at home in this lovely rustic cabin on the lake. We had to work with Thomas to solve some unfortunate complications during our stay, including a dead rodent in the sink, a lack of sheets and towels, and taking our trash with us. However, we loved the home and had a wonderful weekend in the area. Thank you!

Had a wonderful time staying in this home! Will definitely come back in the future. We felt very comfortable and safe.

We enjoyed our stay at Madelyn’s place for our weekend ski trip. It was conveniently located close to Killington and was fairly spacious.

We really enjoyed the cottage next to the river. It was during Xmas break so quiet and snowy. You can hear the water current of the river out back, so it had a peaceful feeling. The interiors were just renovated so felt like a brand new home. The detailing was very well done and felt more like a home than an Airbnb. We definitely recommend it for a family as there are two bedrooms and a loft with 2 beds. David was very responsive so no worries. Also the area has nice Vermont towns to visit. Hanover, NH is nearby - home of Dartmouth College.

We stayed at the beautiful Lull Brook cottage and felt like we were in a snow globe! It was cozy, peaceful, and somehow even more beautiful than the pictures could even show. We are already talking about going back sometime in the warmer months. Heidi was kind, responsive, and left wonderful recommendations and information for us to make our stay enjoyable and easy. If you are considering staying here, just book it. You won't regret it!

Olivia's cabin is a wonderful cottage, perfect for two, or even two with kids. The cabin has wonderful views of the lake and the turning of the fall foliage. This was a warm, cozy cabin with a well equipped kitchen, comfortable living area, and warm bedroom.