Kid-friendly holiday rentals in Windham

Absolutely amazing place and experience. Everything about the place was great and the communication and service was the best. We received 5 inches of snow on our last night and they even had the driveway all plowed for us first thing in the morning. That was a very pleasant surprise. Highly recommend!!

We had an amazing stay at Wanderlust in Windham for our friend’s 50th birthday, with three families (6 adults, 5 kids). The house was perfectly designed for groups, giving the kids plenty of space to enjoy while the adults had their own areas to relax. The ski-in/ski-out access made getting to the mountain effortless, and after long days on the slopes, the hot tub and speakeasy were a huge hit! The house had everything we needed to unwind, celebrate, and make lasting memories. The host was incredibly responsive and helpful—when we encountered a tripped breaker and needed to troubleshoot the hot tub, they provided clear instructions within minutes, making the whole experience stress-free. Overall, this was a fantastic stay that allowed us to focus on enjoying our time together without worrying about the details. Highly recommend for anyone looking for a spacious, well-appointed, and conveniently located getaway in Windham!

It was a perfect getaway for my family - everyone enjoyed themselves, it was child friendly and very relaxing after a big ski day. It is 3 min from Windham Mountain Club, great restaurants and Markets, and we loved sitting out by the brook and having coffee on the deck. We hope to go back next year!

Beautiful home! Very convenient to Windham mountain/town. We would definitely stay again

What an excellent stay - this airbnb was incredibly well stocked with kitchen supplies, games, extra linens, really anything that one could want. Amenities were high quality and very thoughtful.

Amazing place and surroundings! Were looking for a peaceful weekend away and it was just perfect - Kitchen had everything we needed for home cooking and a closet full of board games for some great family time - The view is breathtaking and a great firepit and small creek just below.

We spent the weekend in the area and Tim’s place was fantastic. It’s loaded with charm, comfortable and very well appointed and stocked (right down to treats for the dog). The location is beautiful and the views are amazing. Can’t wait to return!

This place is truly magical - there aren’t many place that offer you a private waterfall and creek for the weekend. If you’re looking for peace and quiet near the sound of a running creek and waterfall, this is the place!

We stayed 2 nights at Bob and Jackie's place with our 2 kids. The apartment was clean and prepared for our arrival which we really appreciate (an extra bed was already made for our kids to sleep). There was enough space for the 4 of us, the kitchen is fully equipped too. Although it was raining heavily during our stay, we could enjoy our time outside because of a little covered area on the back of the building with a view to the woods and a grill that we enjoyed using as well. Thanks Bob and Jackie for a nice and peaceful stay!

Cute, cozy, clean, and super close to the bike trail! Perfect stay for a weekend exploring the towns along the trail.

We loved how quiet and peaceful the location was. We also loved the homey touches- the local books, the honor store out back, the fact that there was the cafe under the apartment. The setting was beautiful and we loved falling asleep to the sound of the brook and the spring peepers!

Wonderful stay! Beautiful home and so much to do in the area. We had a great time!

Theresa was an amazing host, she clearly communicated with us along the way, and made sure we had our privacy & provided the upmost comfort. Her space was well kept and full of considerate touches to facilitate a relaxing stay, the subtleties go a long way. We enjoyed the hot tub in the snow, shared a few stories of skiing adventures & loved the friendly visits from Ben. The views were picturesque to boot, we definitely plan to come stay in other seasons.

Absolutely loved my stay at this amazing place! Anna was incredibly kind, responsive, and made sure everything was perfect during my stay. The location and comfort of the place made my trip unforgettable. I will definitely come back if I ever get the chance to visit again. Highly recommend this place to anyone looking for a wonderful experience!

We had a great time at the Catskills and enjoyed our stay comfortably at the Catskills Village. We didn't bring a car and were able to explore the town by walking and Ubering to Hudson (with a wait time, as expected). Tommy and Jenna gave us some recommendations, which made planning for the trip easier. The space was perfect for two, with the bathroom on the second floor and the bedroom on the third floor. Everything was as described (we loved the interior design!) and perfect for a weekend getaway. Great location for a peaceful time away from the big city. Thank you Tommy and Jenna!

Very convenient stay traveling with an infant. Interior was very chic and simple. Great location on the main strip and easy access to a lot of beautiful hikes.

This condo is absolutely beautiful and comfy! We especially love the bed and pillows.

Luiza was a wonderful host. She provided detailed check in and out instructions, as well as local recommendations for our stay. Her place was exactly as pictured and cleaned wonderfully for our arrival. We hope to be back for another ski trip!

My husband and I attended a wedding and stayed here for 3 nights. It’s was such a lovely stay! A quiet street (with a street light right across the street), and a warm welcome as we entered the door. The place looked exactly as described and was a cozy place to land after the long days out. The shower pressure was also awesome and helped soak away the day. Anna was the perfect host! She made sure to let us know that we may not have service up there and that we should take down all the information in advance and was super proactive in all communication. We truly enjoyed our stay and would definitely stay here again if we’re in the area.

Cozy apartment, walking distance from the water front. Had a great weekend getaway.

Mary’s place is nice and clean, right in the center of town. Walkable to restaurants and coffee shops. Without going into details, I’m touched by her responsiveness to me during my stay – a true life champion! Very best wishes to you, Mary :D Thank you for the recommendations and great hospitality. Cheers~

first of all, Million Dollars view. You have beautiful mountain right in front of this property. I stayed at this place for a weekend get together with family, and wished we had stayed longer. The place came equipped with all the pots and pans you'd expect from AB&B plus coffee maker and pods. we enjoyed their collection of movies. There are grocery stores within minutes from this place and nice restaurants a short drive. we also enjoyed nearby hiking trails. overall, we had a great time and would definitely come back.

Great host, responsive and accommodating! Place was clean and felt right at home away from home! Check in and check out was easy, parking on site, nice neighborhood, cozy place, will definitely be staying here again!

Just a short stay but all was seamless. Beds comfy, bathrooms clean and updated. I would stay again.