Guesthouse vacation rentals in Windsor County

A wonderful ski weekend! We spent two nights and spent the day (Saturday) skiing at Killington. Quiet drive there and back so it was a perfect location to come back to a peaceful evening. Hot tub was amazing after skiing and very clean! Laura and Aaron were very helpful and let us know the conditions of the roads prior to our arrival. Flexible, kind and friendly! Would stay again for sure.

Thank you Tracey! We felt right at home and appreciated your communication and flexibility. Would love to come again. Enjoyed the natural surroundings and local hikes as well.

We enjoyed our stay at the Carriage House very much. Jennifer is a great host - very attentive with excellent communication.

Dave is such a kind and welcoming host! He is great with communication. The place is such a nice and cozy space to relax and enjoy the nature around you. I used fire pit for both nights I was there and it was so peaceful to sit by while hearing the water from the brook. Will definitely be visiting again soon!

These cabins are a wonderful dog friendly place to stay. Super comfortable and clean, and Nick is one of the most accommodating and helpful Airbnb hosts I’ve engaged with. I will definitely be returning!!

My second time renting the yurt. It will become a yearly getaway! A great way to escape the city, be surrounded by nature, snuggle up with a good book. Looking forward to next year!

Clean and comfortable space for 2 in Hanover, New Hampshire close to downtown. The accommodations were as advertised in the listing.

Our stay was lovely! We liked the privacy and the view of the VT landscape was beautiful! It had all of the amenities we needed for a nice relaxing weekend. Heather and Peter were accommodating of our late check-in and helpful and kind!

Nice place. The biggest drawback no kitchen. Basic one bedroom, small table sitting area, small bathroom. Private entrance. Neighborhood is safe. Must drive to restaurants.

Second time staying here for work, would definitely recommend to others needing a place to stay in the area!

Beautiful home and property. Even in the rain the view of the mountains was picture perfect. Easy to get to other areas of VT. Comfortable beds and roomy couch/living space.

This is an absolutely gorgeous place to stay in Vermont and we loved it!! The living room and bedrooms are all elegantly decorated and also very cozy. More importantly, Madeline and Parris are the best hosts we have ever had. We came to Vermont for a ski trip and ran into some snow-related issues on our first day. Madeline and Parris were very responsive and offered tremendous help to us. Overall, a beautiful house with great hosts for an amazing stay!

Jeff’s place was perfect for our two family ski trip. Our kids especially enjoyed the basement and there was plenty of room to spread out. Well equipped kitchen and big open dining/kitchen/living area were great for cooking and eating together. We had a great stay!

Great place, beautiful house. Easy short walk to the trail.

Stephen's place is conveniently located to Okemo and amenities are perfect for a weekend trip.

Options are limited when we travel our with two dogs so we felt very fortunate to find the home in Weston. It was perfect for the two of us and our two dogs. The home had most of what you would expect as far as extras and everyday items. We loved the area we were in and the proximity to Londonberry and southern resort mountains. I would recommend the home to anyone with a small group. We will rebook next year if the cost doesn't increase.

My daughter and I had a great stay at Rose’s place. The kitchen was clean, and we were very close to the Skyeship gondola at Killington. We enjoyed watching tv with the electric fireplace keeping us warm and cozy.

Stayed here during a summer trip with a family of 4. Amazing location - one block off of downtown and one block from Shaw's. Parking / check-in / everything was easy. Place was super clean and all appliances / equipment / linens / etc. were new / lightly used. Only potential issue was that the first level ceilings are pretty low, but If you're under 6'5", you will not have any issues. Communication with Nancy was great and all-in-all highly recommend / great value.

What a perfect little getaway spot. Spotless, well-appointed, thoughtfully designed. Close enough to all the special things that Woodstock has to offer, but sweetly tucked back from the road. Michael provided excellent communication, helpful instructions, and wonderful local recommendations. Highly recommended.