Family-friendly vacation rentals in Windham

Nice place thanks Mike

Mark's High Pocket Bed and Barn was absolutely stunning and cozy. My friends and I stayed while attending a wedding nearby, and were so delighted by the home the minute we walked in. Thoughtful furniture and decoration through out the house, as well as beautiful yard and walking paths that were so nice to explore on a sunny spring day. The home was immaculately clean and well stocked. Mark was very communicative and responsive. We would all very happily stay at this home again!

Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.

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.

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.

Had an awesome weekend here with the family! The cabin had everything we needed, super comfy and well-stocked. The hot tub was a huge bonus, and the hosts were super friendly. Would definitely come back!

Tesha's place in Ludlow was exactly what I needed- the rare combination of a private, quiet space in a natural setting which also provides all the comforts of home- and some extra luxuries too! The listing photos don't do it justice and immediately upon arrival it's obvious a lot of effort was put into ensuring the place provides guests a wonderful stay. Next time I need to escape the city I will definitely be checking to see if it's available.

My family loved staying here! There was plenty of snow for activities. We went skiing at Mount Snow and ice fishing on Lake Raponda for a day. The barn is so unique and had everything we needed. There were lots of extra pillows and blankets and a big cozy couch to curl up and relax by the wood stove. Having access to the clubhouse was amazing… the kids loved swimming in the warm pool after a long day outside. Brian was super responsive and easy to talk to! We already want to go back!

Great little studio apartment attached to Emily’s house, very peaceful yet walkable to downtown Wilmington!!! Easy to get to the Hoot and Toot trail, and about a mile from the boat launch/picnic grove at the lake!! Absolutely would recommend and stay again!!

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!

Our weekend stay at the cabin was exactly what we hoped for. Denis’s place had everything for a comfortable yet low key weekend. He was very communicative, friendly and helpful before and during our stay. The location was quiet and beautiful but also close to town. We hope to stay again next time we’re in Brattleboro!

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.

Wonderful place with great family room with fireplace especially when your weather doesn’t cooperate. The house is well kept and the instructions for everything were placed all around where needed. Fenced yard was great for the dog. The bed in the master is super comfortable with great linens. Loved the house-would live in it in a heart beat. Plenty of games, air hockey table, darts and another game table…grill, firewood- even poop scoops for the dog! Well done!

Needed a home-base for the weekend and Mary’s place was once again (this was our second stay here!) fantastic. Waking up to the sound of the river in the yard from the rainstorm the day before is incredibly special.

I stayed at Angela’s yurt for Memorial Day weekend. It was exactly as described. My boyfriend and I had a very peaceful long weekend. The space was cozy and adorable and we especially loved the wood burning stove. Was a great stay, would definitely return and highly recommend.

Truly unlike anywhere I’ve ever stayed. I can’t recommend this home enough. The pictures do not do the property justice. You will not regret staying here!

A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

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

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!

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.

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

Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!

The place was great, clean, nice bathrooms. The oven seemed like it wouldn't go up to temperature at one point so I messaged the host and they responded right away to get the maintenance folks over. But it turned out that it was just set to Celsius and I was able to look up how to change it online (Hold down the broil button!). There were PLENTY of towels/linens which was nice.

Great spot near the mountain. nice community pool and hot tub.