Kid-friendly holiday rentals in Windham

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!

Great spot for a group of friends for a weekend! We loved the easy and close proximity to Hunter Mountain for skiing + tubing, we were able to walk right from the Airbnb. The amenities like the sauna and pool were a great addition, too, and it was a large amount of space for hanging out! Would recommend!!

My adult daughters and I came up for Presidents Day weekend. There was a winter storm and very cold and windy- even closed the mountain where we were going to cross country ski at. We spent a lot of time in the house. It is clean and very warm and very nicely furnished. The kitchen has everything needed with quality cookware. Beds were comfortable with nice linens and plenty of clean towels. Overall a very nice place to stay.

Despite booking my stay with three other friends for my birthday during February, it was the absolute best decision. Everything was as described, lot of great in-home amenities including games (i.e. ping pong, pool, tons of table-top entertainment.) Scott was absolutely one of the best hosts I have coordinated and communicated with. He would check-in to ensure we had what we needed and when there was a heavy snowfall the evening prior to our departure date- he immediately checked in and had the walkway and driveway cleared of snow. Lot of great, beautiful hikes in the snowfall and do hope to have the opportunity to return during the warmer season. Thank you, again, for the wonderful accommodations and for being such a proactive and communicative host!

Second time we stay at Chelsey & Dominic’s place. They have a gorgeous home, with beautiful surroundings. The house is tastefully decorated, the rooms are very comfortable, and the kitchen is very well equipped. Both hosts are incredibly responsive and they made us feel right at home — thank you!

We stayed at Natalia’s house with another family with kids. The house had everything you could imagine for babies/children. It was beautiful, very nicely and thoughtfully decorated. In fact, it was nicer than the photos. Natalia was responsive and accommodating. We were so happy with the house, the location and hope to stay there again.

John and Kelly’s house was simply wonderful! Their home is absolutely perfect for a family getaway. You will find both peace and excitement given the nature surrounding the home. The view is amazing! Our children had a fabulous time playing in the snow given the landscape of the property. It’s also so very close to town may you need to step out. Kelly and John are quick communicators from the moment you book to the moment you leave their home, they are available for any questions or concerns. We were incredibly sad to leave as we felt right at home. We would definitely love to book this home again soon.

Perfect getaway! This serene house exceeded our expectations. Ideally located for college tours (just 1hr from SUNY Binghamton and 1hr from SUNY New Paltz). We explored nearby both colleges gems: Walkway Over the Hudson Bridge, Minnewaska State Park, and enjoyed dinner at Courtside Bar/Grill in Binghamton and “El Paso” in Highland. The house has everything needed for cooking; we loved using the indoor chimney and outdoor stove for grilling. The private creek and outdoor space are breathtaking - can't wait to return in summer! Don't hesitate to book; you won't regret it!

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!!

This place is fabulous! I was looking for a place for a long weekend retreat and was delighted to find this listing. The apartment is large, well appointed, and very clean. Below is a gorgeous spa/yoga center, where I treated myself to two treatments over the long weekend. All around are great restaurants and shops. I didn’t get in my car once after parking because I just wanted to soak up the serenity of this apartment, the spa below, and the historic street in Hudson. I envision returning with my husband, with friends, and alone for another personal retreat. Thank you for such a great stay!

We had an amazing stay! The Airbnb is in a great location, right on Warren Street and within walking distance to everything. The decoration was charming and quaint, giving the space a cozy and unique feel. John, the host, was incredible—he was always on top of things and provided excellent recommendations that were all on target. Highly recommend this spot for anyone visiting the area!

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.

Lovely place with the essential and for a nice weekend. I didn't mind 2 flight of stairs but just so everyone is aware

Super clean and well-appointed studio apartment. Cool compact kitchen. Very helpful, responsive host. A nice stay.

We had a wonderful stay in Hudson at this AirBNB. Anthony is a great host. The apartment is bigger than appears in the photos. This visit to Hudson was to celebrate a 60th birthday, and was perfect for a ladies overnight. After parking the car upon arrival, we didn't use it during our stay. We walked everywhere. We will be back for sure! Highly recommend if you love to eat, drink and shop!

We had a wonderful stay at The Hudson Milner. The Bowler Hat was exactly as we expected, the location was ideal for exploring everything that Warren Street has to offer. We’d definitely book again!

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

The condo met all of my expectations and was exactly as described. I appreciated the clean, uncluttered decor as well as the lovely fireplace that the owner took care to make sure was well stocked with wood and ready for our use. We happened to be there during a particularly cold and windy February break and really appreciated it. I cannot thank our host enough for her hospitality - you get a 10+.

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.

⭐️⭐️⭐️⭐️⭐️ Amazing Stay! This Airbnb was perfect! The space was spotless, beautifully decorated, and had all the amenities we needed. The host was incredibly friendly and responsive, making check-in and our entire stay seamless. The location was right next to the slopes but still peaceful. Would absolutely stay here again. Highly recommend!

Great spot for a night in Kingston! Good location to get anywhere in the town and very clean!

Hannah was extremely responsive at all times. She even provided us with Oat Milk for our coffee! The water does have a sulphur odor but no worries there is a big water dispensing for drinking if so desire. Place was clean, quiet and perfect for our stay in the Hudson Valley.