Family-friendly vacation rentals in Windsor County

Nice place thanks Mike

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.

Nice space for a group, plenty of room for dining and relaxing. Clint was very responsive and gave excellent instructions. Appreciated the hospitality!

This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!

Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!

We had a great time at David's place. The kitchen was well stocked, plenty of firewood, and the hot tub was ready to go. The house was very clean. All the bedrooms had plenty of linens, and extra blankets. We would definitely stay at David's again!

Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

Great place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend

Marinas little red cabin was perfect for our ski trip! The WiFi is a little rough but we didn’t spend much time on our phones Bring dvd’s (the collection is solid but more the better) Perfect distance to okemo, Stowe is less than two hours so it was great! The cabin felt so cozy and felt right at home! Would def book again!

We had an awesome getaway at Kevin and Lesley’s cabin! This was our last little getaway before we get married this fall and it was the perfect unplugged retreat to feel connected going into the stressful time before the wedding. The cabin is cozy, the bathroom is adequate and sort of surprisingly not as buggy as it could have been, and the porch was my favorite spot to feel connected to nature. Kevin was very communicative and the instructions in the cabin were very clear. Luce’s lookout was amazing at the top and a really great recommendation by our hosts. We would definitely go back!

Watching my first incredible sunrise, I started planning my return visit… Prior to arriving, Laura provided detailed instructions and directions and was very responsive, even providing her cell number. She met me at the apartment to welcome me to Vermont and showed me around the property and provided all the necessary instructions. She was communicative throughout my stay via cell. The apartment is absolutely perfect for a solo traveler (I also had my dog) or a couple seeking some quiet solitude in nature that is still very close to a wide range of activities and conveniences. I came to have some quiet time alone and to ski, and I had plenty of both. Okemo is maybe 15 minutes away and Killington is just under an hour. Stratton and Mt Snow are about 45 minutes south. I highly recommend Laura’s property and plan to return next year. Thank you!

We enjoyed staying in Heidi's Hancock Hideaway! We enjoyed the peaceful, quiet & comfortable place. We enjoyed taking walks, sitting on the porch during the day & star gazing at night. Kitchen had everything we needed to make & enjoy our meals. Heidi made sure we had clear directions with perfect details to arrive at the Hideaway. We even had fun staying in and doing puzzles during the rainy days. Our dog enjoyed laying in the sunshine outside & in front of the windows. Local recommendations were great.

Had a wonderful stay at the “Birdhouse on wheels.” Waking up to the stream was so peaceful. Make sure to look up at the stars on a clear night. Just a heads up (pun intended) to those on the taller side for the sloped roof.

This is a nice cozy attic apartment inside of a residence. Steep staircase. No living room. Wonderful walking area beside a river. Close to Woodstock and Dartmouth. Gracious host. Temperature a little difficult to regulate. Recommend.

What an amazing stay! Angela was amazing and she left instructions for everything which was super helpful! We loved our yurt stay!!!

The house more than met our expectations! We skied at Killington and Sugarbush and snowshoed on trails behind the house. The house was very cozy and quiet with a large kitchen and very cozy spots to read and sleep in after a long day of being outside. I highly recommend staying here!

Our family had a wonderful stay at the condo in Killington. The location could not be beat! A very short 5 minute walk to the lifts and Snowshed lodge. The complex had an amenity building with pool/hot tub that the kids loved and the condo was quite spacious and clean. Ruslana was a great host and very responsive! There is a solid chance we will be back next year!

Amazing stay. Loved how close it was to the mountain. The pool also looked amazing so sad it was winter. Definitely recommend staying there were 4 beds and can comfortably fit 5-6 people.

Nice cheaper lodging on the access road

We thoroughly enjoyed our stay with 5 adults and one dog. We walked in and immediately felt at home. This was one of the most well appointed places I have ever rented...it had everything we needed and more . The kitchen and the living space was quite comfortable. The beds were wonderful. There is a trail to the river right across the street which we used several times. I can't think of a negative thing to say.

Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.

A wonderful place situated close to the mountain. The amenities were fantastic as well. The only issue was getting the right pin to access the apartment...however Scott responded within seconds so it was minimally disruptive.

Great spot for a week of skiing! Danielle was very helpful and communicative throughout