Kid-friendly holiday rentals in Windham

This Airbnb is completely amazing. It is beautiful. It is spacious. It is great for a group. It comes fully stocked with most of the basic things you need like a fully functional kitchen with things like syrup and jam and all of that in there. The host was completely responsive. If you are planning to go to ski, it is close to the mountain. I completely enjoyed our stay.

We stayed as a family of 4, including a 1 year old and 3.5 year old. The place was extremely comfortable and had everything we would need for our stay. The kids enjoyed the playroom and kids room with lot of toys and books. Kitchen was fully stocked with plates, utensils, cooking ware, and a high chair. Place could easily accommodate more people, very clean, comfy beds. Property manager was very responsive. Short drive to downtown area. Lastly, great outdoor area, we’d love to plan a trip there when warmer as well!

Cozy and practical, the Elliot house was perfect for a family stay. Our hosts made the small conveniences available in their kitchen - items such as condiments, coffee, and tea which were very comforting after a long day of travel or hiking. We also greatly appreciated and enjoyed the thoughtful s'mores goodie basket that our hosts provided. What a treat!

This home was perfect in many ways. The home itself is bright with sunshine, has a beautifully-updated persona while keeping its mountain cabin charm. The kitchen was well supplied and we were able to cook meals easily. We also enjoyed the selection of books and games during the evening hours. If we still had young children around, they would have loved the fun kid's room upstairs! Plenty of available hiking nearby with a good selection of local restaurants for various libations and meals. Working with Julie was super easy - communications were quick and simple. No problems at all - a very excellent place for a relaxing holiday!

Lola's place was clean, quiet, comfy and well situated for our needs. The house is well equipped, including butter, milk and eggs in the refrigerator (nice touch). Lola is very responsive, answering any question we had in a timely manner. We would definitely recommend and stay here again.

My daughter and I spent a lovely weekend at Chelsey and Dominic’s house. It was the perfect place for reading, laughing and lots of conversation. Easy to get almost anywhere in Hudson Valley. We enjoyed walks around the property and seeing quite a lot of wildlife. The setting is truly magical.

We had a lovely stay! The place was very relaxing, peaceful, and surrounded by nature, yet still close to Woodstock. One of the highlights was seeing a family of deer right outside our window — such a special moment. The hosts were also incredibly accommodating, providing a highchair and pack ’n play for our infant, which made our stay so much easier. We truly appreciated their thoughtfulness and hospitality. Highly recommend to anyone looking for a quiet getaway close to town.

This is the first time a listing with "kid friendly" has truly fit the description! We have two littles and Neesha's home did not disappoint with safety guards, toys, books, games, crib and small beds. Everything was available down to the highchair, noise machines and monitors. Anyone who travels with kids can appreciate having all of these necessities available and ready to use. It's a whole suitcase less for the trip! The home itself is beautiful, pristine, spacious yet still very cozy. It felt like a quiet family retreat with our own jungle gym in the backyard and a fire pit for smores. The town of Kingston was not far away - we rode the Polar Express. And for more adventures, Woodstock is super close and has great shops and restaurants too. But we didn't have much desire to leave Neesha's home. We loved the chef's kitchen (fully equipped) and had many family meals in the dinning room. Our host was very responsive and accommodating. We will definitely be back.

We have stayed here more times that I can count. Bob and Jacki's place is a great get-away. Comfortable, cozy and so clean and well stocked for a longer stay. If you see how many times I left a glowing review you will see I mean it since we keep coming back. It is our go to spot when staying in the Catskills. Thank you as always, Bob and Jacki!!

My family had the best stay! Loved the funky decor, comfy sheets, and the amenities. Felt right at home! Couldn't have asked for a better spot!

We had an awesome experience! I would recommend staying here! The place was clean and looked just like the photos. It was super comfortable and had a nice ski cabin feel. John was super communicative and helpful throughout our stay.

My family and I loved staying at Tj’s place in Hudson. The apartment was beautiful and exactly as described. Four of us stayed there for a week and we were very comfortable. Tj was very responsive when we had questions or issues (which we didn’t have many of since instructions were super clear). I also enjoyed the multiple yoga classes and spa sessions I participated in at their spa downstairs. The instructors and providers were all super friendly! The town of Hudson is incredible for anyone who loves to shop, look at art, and eat good food. It’s small, but there’s so much to see and eat! Everyone in town was genuinely friendly and welcoming. This was exactly what my family and I were hoping for for our vacation. We’re grateful we found Tj’s place!

My daughter and I had plenty of space to spread out. John’s place is very comfortable, clean, and charming. Thoughtful touches like extra hooks, suitcase stand, and bench at the entry to take off our wet shoes after a rainy Spring day in Hudson. Easy walk to great coffee shop and restaurants. Would definitely return!

Orna was so welcoming and easy to communicate with. The apartment is cozy and well appointed. We were visiting our daughter and family for Thanksgiving. They recently moved to Kingston . Great location! This would not affect most people, but my 90 year “young” dad was with us, so the old fashioned tub/shower was a bit of a hazard for him. Really a gem of a place if you are traveling through or visiting loved ones in Kingston.

Great place to stay. The hosts are great and very communicative. Close to a bunch of food spots as well!

Wonderful place. On Warren, there’s gallery, and next to it, doors. You enter on floor 1 of a townhouse, dark wood banisters, lovely, decor and art…you head up two flights of stairs passing charming accessories. Top of the stairs, 2 doors - one to the bowler and another to the top hat I believe. enter the bowler and you’re wowed. it’s high ceilings, lovely creaking floors. glorious top floor of a townhouse feeling. spacious. even more than the pics suggest.

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

Pristine clean, cozy, one bedroom condo unit located in Windham with seasonal access to tennis courts and a pool. Walking distance to the beautiful Windham Path. Slept better than at home in the comfy bed. Went for two days of midweek remote work. Agnieszka, the host, was gracious and responsive. The host obviously put some genuine TLC into this place and it shows. Browsed for books at Briars & Brambles, an indie bookstore in Windham adjacent to Windham Pharmacy. Purchased groceries and firewood down the road at Hickory Hill Market . Ate in area at Higher Grounds and Windham Diner. Living room has a fireplace with large screen TV just above. Great for all seasons. Thanks Agnieszka!

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!

Cullen was an exceptional host. The space was exactly as described, with plenty of supplies. Communication was stellar. The condo had plenty of extras like clean linens and blankets, there were even additional chargers set up and toiletries if we needed. The beds are comfortable. The bathrooms very clean and updated. Parking right in front. We felt safe and comfortable. This AirBnB is 5 minutes to Windham mountain and minutes from Town. Plenty of places to eat and shop. I highly recommend this Host and property. If we ever go back, we will try to re-book with Cullen.

I highly recommend Suzanne's place for anyone visiting Windham! She was incredibly responsive and helpful throughout the booking process and my stay. As someone who travels constantly for work, my schedule can be quite unpredictable, and Suzanne was unbelievably accommodating and flexible with my changing needs. I truly appreciated her understanding and willingness to work with me. The location is fantastic, right in the heart of Windham, and the view of the ski resort from the back deck was an unexpected bonus! I only wish I could have stayed longer. I'm already looking forward to my next visit, not just for winter skiing, but also to explore the beautiful surroundings throughout the year.

Great people great location I would definitely recommend others and a great price

The place was exactly as described and she was really attentive if I had sent a message and it was extremely clean and cozy.

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