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!

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 was a great house in a lovely spot, can’t wait to come back. It was very comfortable for 4 adults and 2 toddlers. Plenty of room to cook, eat, do puzzles, play, read and relax. The house has a charming, cozy feel and is clean and well maintained. Hosts were kind, helpful and great communicators. Thanks Julie and Pierre - we’ll be back!

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.

Scott's place was great. We were so relaxed and felt right at home. We will be going back which is the best compliment I can give an AirBnB. The views were beautiful!

We had a wonderful stay at Stony Hill in Pine Plains. The house was beautifully designed and well equipped for a winter jaunt with cooking at home and sitting by a warm fire. The hosts were very responsive and helpful throughout the process. Would love to come back again!

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.

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!!

The apartment was very cozy, well equipped and the furnishings had a fun vibe so it was perfect for a weekend stay. We loved being right in town so easy to wander the cute shops and go to restaurants. We would book it again if coming to Hudson.

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.

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.

Loved this spot in Catskill — super clean, bright, and the living room was so nice to hang out in with an amazing view. Great walkable location, definitely worth the trip. Also wonderful linens. Thanks for a great stay!

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.

Convenient, sweet stay minutes away from windham. Agnieszka was super responsive and the house was perfect for a couple

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!

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.

This was probably my favorite rental to date. I had to travel over a hard situation and it was the serenity that I needed at the end of the day It feels so cozy and really represents an escape away from home Jasmin and Ryan are wonderful easy to work with helpful and even helped me with recommendations close to the unit Plenty of blankets and amenities to enjoy thank you Jasmin and Ryan. I will be definitely contacting you again. The next time I come to that area.

Great condo, comfortable and upgraded amenities! Great location and easy to get to. very communicatelive host!

Could not recommend this place enough! Darla and Matthew are extremely communicative, sent lots of great recommendations, the house is very cozy and well-stocked, the neighborhood is walkable to lots of great shops and food, and the check in and check out process was a breeze! Would definitely stay again. An amazing value for the price.

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.