Family-friendly holiday rentals in Windham County

John's home was perfect for our group of singers to have a lovely retreat together - clean, quiet, plenty of space for us all to both spread out and be together, beautiful view, cozy fireplace, relaxing hot tub - really all we could have hoped for. He thought of everything, from a well equipped kitchen, to wood and newspaper for the fire, to a supersized chess set. John was most welcoming, flexible, and clear. Highly recommended!

Wonderful stay. The location was private and relaxing. The home was well stocked with all the amenities. Having the lake and kayaks available was perfect. Summer evenings under the stars and fireflies. Host was responsive and friendly. Look forward to staying again!

Lee’s house is peaceful, clean, spacious, and had everything we needed (well-stocked kitchen, grill, reliable WiFi, games, etc.). The hot tub is the star of the show. Lee is super responsive and accommodating. 10/10 recommend!

Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.

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

We had a wonderful stay! It's such a beautiful and unusual cabin. It would be great for two couples as there are 2 equally great bedrooms that are quite separate, and a very nice sitting area around the amazing wood stove. (Which we didn't use because it's June and not necessary.) The hot tub was such a treat, and the bedroom with the boat was so cool. (OK, so maybe the bedrooms aren't quite equally great.) The kitchen is outstanding! We sat out on the porch a lot looking over the meadow, and I really liked that we were able to bring our dog. About the notes and instructions: they didn't bother us at all. There's a few non-intuitive features of the cabin, and it was useful to have clear guidance on those things. I want to make clear why I gave 4 stars for "cleanliness". I think they do an excellent job cleaning this cabin! But a rustic cabin like this is impossible to make "5-star clean". If you want or need that level of cleanliness, then "rustic" isn't for you! Go find a nice hotel.

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.

Great place to stay with wonderful amenities!

Really lovely Airbnb in a beautiful location! I came with my dogs and they were right at home. This spot was truly a dog friendly location. They even provided dog bowls and beds! There was also a ton of room to run and play with them. You really can’t beat the location and view if you want to get away. I love that there are chairs both on the patio and in the lawn to enjoy the view. My husband and I were looking for a place to truly check out and get away from work and this was the perfect spot for that. The bed and couches were really comfy, the kitchen had all the basics and I love that there was a fireplace option, even if we didn’t need it. It rained a ton while we were there and the yard gets pretty soggy, so if you’re planning for outdoor playtime on a rainy day, bring your rainboots! 10/10 stay and we’re already talking about booking another weekend there.

Our group loved staying at Lilac Ridge- what a perfect Vermont location, said a first time visitor to Vermont, and even those who live locally were impressed by the classic farmhouse vibes. Rooms were tidy and uncluttered, there was plenty of space for everyone to be comfortable. Communication was excellent, Amanda was there to orient us upon arrival, extra care was taken to make sure we had what we needed. The maple soft serve and cute farm stand were an amazing addition. The low-traffic dirt road is a great place to take an evening stroll or to ride a bike. Thank you!

We had the most lovely stay at Pincone Pond. The house is absolutely spotless and well stocked with everything you need in the kitchen, shampoo and condition in the bathrooms and throw blankets for the cool evenings. The house is so homey and comfortable and the grounds are stunning. Beautiful yard and pond which were well cared for. Catherine has thought of everything including chairs for sitting by the pond or fire pit. Just a lovely, peaceful spot.

A great spot, only a short drive from downtown Brattleboro. The host was friendly and responsive. It’s a lovely cabin and the surrounding nature is very peaceful. It’s a cozy, quiet spot.

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.

We really enjoyed our stay here. The place is incredible, you’ll have everything you’d need. Full of very thoughtful details. Very cozy, confortable and charming. The surroundings are beautiful and in a short drive you’d find anything you may need in Brattleboro. From dining to great coffee, groceries and more… I loved how simple and easy where the instructions for check-in and Out. Katherine was very friendly and responsive. Would definitely stay there again.

Mary was a super good hostess and she even left us a welcome basket full of goodies including Bogle red wine (cabernet), coffee, and other treats plus homebred brownies in the fridge! We loved the chalet and the beauty of it inside and out with the greenery of the forest and the brook which our dog, Beau, got right into it and loved it! We all enjoyed the area and the cozy home with the room to spread out and hear the rain as we were snug inside. The bed we chose to sleep in was comfy and warm and I (Carolyn) loved having coffee on the deck of a morning with Beau. We enjoyed our long walks down the road and the town of Dover was fun to visit as well as the beautiful wedding we attended over Wilmington not far away. It was a wonderful stay and we certainly love Vermont! This was our 4th stay in Vermont between the years of 2004 - now. Our first "Dog Vacation" took us to Brattleboro, Middlebury, Willoughvale with Lake Willoughby, and last summer to White River Junction and Barre. Fun!

so beautiful and cozy! private and in just the right location.

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!

Amazing experience! Everything was prepared and fully equipped for us, from towels, soaps and shampoos, even spices and oil in the kitchen! Definitely recommended, and we will be happy to visit there again! summer or winter!

We were in town for a family wedding and this was the perfect place for 20 or so of us to spend the weekend. Everything was great. We were so comfortable and had so much fun! Thank you to Meiling, Martin, Mayra, and all the folks who assist them with housekeeping and logistics. Hope to find an excuse to return, as everyone was sorry when our stay came to an end. Highly recommend without hesitation.

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.

The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

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

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.