Family-friendly vacation rentals in Windham County

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!

We loved our stay at Lee's place! The place was clean, the kitchen was well-stocked, and plenty of space for everyone. We would definitely stay there again.

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.

Absolutely stunning!!! We fell in love with this little gem. Everything was perfect. Loved being out in the hot tub and enjoying the wildlife. So nice and peaceful. Place was immaculate and had wonderful charm. We are definitely coming back again. Thank you Ben!

We had a nice getaway at Paul's place. The place fit our needs perfectly. We enjoyed the use of both the indoor and outdoor pool. You do need to reserve times online for use of the pools or other activities but we never had any issue with that. There are several great restaurants nearby and we enjoyed walking the nearby trails and shopping in Wilmington and Dover.

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.

Perfect home for a mountain escape . Beautiful kitchen, hot tub and sauna. Hope to come back again

Nicholas and Jenna are great hosts! We were beyond lucky that they shared their home with us! The views were great, so great that we eloped here! Cute cozy home pushed off the road with a beautiful view off the back deck! We would love to back to visit!

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!

Denis is a great host . What an amazing family and what an honor you let us stay! 100% will be coming back!

My family and I just returned home from a wonderful ski vacation! The home was just as pictured and the surroundings were absolutely beautiful!The house was immaculate and the ambiance was warm and welcoming. We had a great time skiing at Mt.Snow (30 minutes),exploring Brattleboro (12 minutes),preparing meals together and just spending quality time with each other! On another note….. Cat and Ed were very responsive and were always available if we had any questions! My family and I are already looking forward to returning next year ! Thank you again for EVERYTHING! Carol and Gene

We had a great experience with Erin and our stay! Erin was incredibly friendly and welcoming. She made sure to respond promptly to all our questions and requests, which really made us feel at home. Erin went above and beyond to accommodate our needs, ensuring we had everything we required for a comfortable stay. Her genuine care made our experience truly special. If you're looking for a wonderful host and a cozy place to stay, I highly recommend booking with Erin.

Place was clean, responded in a timely matter and looked exactly like the pictures! What a great experience ‼️

This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

We loved our stay at Apple Blossom. A treat to take our dog and explore the area. We enjoyed the local hiking, breakfast in the sunshine on a beautiful picnic table and walks around the property visiting the avery. Overall we had very relaxing and peaceful stay.

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!

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.

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!