Family-friendly vacation rentals in Windham County

Great for a group ski weekend. Plenty of space. Close to Mount snow. Has everything you need to cook a meal. Would definitely rent again!

Great place! Clean, spacious, with plenty of amenities. Owner was great. Flexible. Communicated clearly and promptly. Would definitely stay again.

“This house exceeded our expectations! It is incredibly spacious, making it perfect for families or groups. The home is well-stocked with everything you could need, from kitchen essentials to extra toiletries. The attention to detail in providing a comfortable and convenient stay is truly appreciated. Highly recommend for anyone looking for a relaxing and well-equipped home away from home!”

Great location. Beautiful views. Host was extremely responsive. Great fire place and living room.

Very beautiful home and lovely host! Would recommend!

This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.

Christopher was always in touch with us to make sure nothing was missing and that we were doing ok. We had a couple of problems with one of the heaters due to the snow but he and Jerry stayed on top of it until it was fixed. The place is really nice for an escape and to get some relaxing time in the jacuzzi. Totally recomended!

Stayed with my family of four for Christmas week. Close to Shaw’s grocery and several restaurants. We went skiing at Mt. Snow and Okemo. The club house had a pool/jacuzzi, ping pong, pool table etc. and friendly staff. The house was very cozy and comfortable. Micheal responded quickly to any questions and was easy to communicate with. Would stay again if we return to the area.

Christina was an excellent host who ALWAYS responded to any of my questions or concerns immediately and courteously. Her space was exactly as described and very spacious as well as a fantastic environment for a group to get together and have a great time! I highly recommend Christina’s place for a great time with a large group, she is the ideal host who works tirelessly to provide an amazing space for her guests!

Nice stay in a comfortable apartment. Friendly hosts in a quiet neighborhood. Close to town and local attractions.

We had a great stay at Lilac Ridge! The house was near and spacious, plenty of room for our family. We stayed in quite a bit and enjoyed the farm (including a visit with the calves!) and the house. The little farm stand had some nice things, including fresh eggs, maple syrup, honey, and soap, all local. Ross and Amanda were super responsive and took care of all our needs. Thanks so much!

Mariann has a great space in a great location. Very accommodating and friendly, made you feel very welcome . Very responsive. Really nice area. Would highly recommend.

This was a very spacious and cozy spot! A perfect place for a quiet weekend getaway with proximity to hiking and/or skiing/snowboarding. There were many books, games, and puzzles available to peruse and enjoy as well.

We recently enjoyed a lovely stay at The Carriage Barn in Guilford. Our host, Katherine, was very responsive to everything we might have needed during our visit: a very easy check in and out process, detailed instructions on how everything worked, items for our comfort (a gift of delicious chocolates, many fluffy towels, silky sheets, etc.), and was easily available via texting. The photos of her restored historic barn are very accurate - it's a beautifully designed renovation and is decorated with lovely art pieces, cozy furniture, and a huge library of books for your enjoyment. The tv works great and so does the WiFii. We traveled with our small dog and there is a baby gate available that easily snaps onto the staircase posts so I was not concerned about my dog's safety.. Best of all is the beautiful views of the gorgeous Vermont countryside. You'll see lovely sunsets here and spectacular sunrises. It's a great spot to truly relax.

Immaculate Vermont cottage built by her husband’s parents. The touches on the home, property and even down to a welcome basket made us feel at home during our time in Dover. The backyard is absolutely beautiful and I can not wait to return in the summer!

We enjoyed our stay at Domenic with 2 kids on school break! The tiny house is just as described, colorful, well organized and very comfortable. We enjoyed making a fire outside on a beautiful spring evening and checking out the peacocks!

Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!

The staff of Upper Pass lodge was super friendly and helpful! From the hotel staff, restaurant crew, and house keeping- everyone was fantastic. They really take Vermont hospitality to the next level. We hope to visit with them again soon.

Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again

We had an amazing stay at this home. The house itself is well-decorated, cozy, and equipped with everything we needed. The location was great, just a short drive to the ski slopes, yet tucked away in a peaceful and quiet setting. It was the ideal spot to relax after a day on the mountain. We loved waking up to the serene surroundings and would absolutely stay here again. We had a small hiccup checking in but Michael was very responsive and helped us out.

Husband and I had a great little ski getaway at Mt Snow. This cozy place was perfect for us! The view of the mountain is awesome. We did find the walk to the mountain (although short) with ski gear to be a bit much and highly recommend taking the Moover shuttle from the nearby parking lot.

Jenny, a superb host! We had an amazing time vacationing in Vermont. There was plenty of space and comfort for everyone. The host was always available, quickly assisting and responding to all our questions. A wonderful house, highly recommended!

We absolutely loved staying here- beautiful and laid out perfectly for 2 families, each with 2 little kids. Super convenient location to Mt. Snow. We look forward to staying here again!