Kid-friendly vacation rentals in Windham

Susanna, Sarah, and James were great co-hosts for our trip to the Catskills. We enjoyed the house, the outdoor space, and the proximity to Woodstock and other areas in the Catskills. We enjoyed our stay and would stay at the house again in the future.

This house was absolutely perfect for two couples and three kids! The outdoor space is gorgeous and we got to enjoy a lovely snowfall on Thanksgiving morning! The house had everything we needed and we only wish we could have stayed longer. The location is also ideal as it feels private and in the woods, but is just a few minutes away from the town center of Woodstock with all of its cute shops and restaurants. Highly recommend!

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!

We had a beautiful Christmas thanks to Julie and Pierre! Gorgeous surroundings and a lovely house - so comfortable and warm. Everyone (including our newborn and family pets) was able to relax and have a good time. And we loved the Ashokan Rail Trail for a snowy hike!

I had a wonderful stay at John’s and Kelly’s home. The surroundings were beautiful, the house was just lovely, and everything was sparkling clean! I hope to come back soon!

Beautiful space inside & out ! Thoughtfully designed and sturdy built new house with stunning views of Catskills and cute neighbor's cows in back field. Chef's kitchen was a welcome perk -- 5 ways to make coffee, all the pots & knives, if you bake bring a muffin/loaf pan. Georgeous sunlight, strong wifi, good heat, weak water pressure but we arrived right after storm and power had been off in subzero temps so that may have affected pressure. Place has 1Q, 1K in bedrooms, sleeping on not-a-sofabed couch was not a thing. Welcomed the intense quiet, thanks for a great holiday 🙌 Thought the $50/ day cleaning surcharge was a little heavy, but it was impeccably clean so worth it -- I am severly allergic to dog dander but did not even know owners have a dog till we saw crate in the closet 😄

Excellent home to gather the family to celebrate the Christmas holiday. The great room is lovely and inviting. This home gets kudos for also having a great selection of cooking equipment, utensils, serving dishes and plates so cooking multiple holiday meals was no problem. The beds were comfortable and living room and game room were nice spots for relaxing. While the road the house is on is not a place for walking there is a quiet road across the way that is perfect for a stroll or run. Everything in the home is well labeled for use which I also appreciated. Highly recommend this home aptly named the Gathering House. Thank you Tommy for a great holiday!

kimberly was great, she gives us events to attend around town and we had a great time. I will definitely go again.

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!!

Jenny’s place was an amazing home away from home in Hudson. The apartment is super quiet and clean, close to everything. Amazing restaurants, bars, and shopping all close by and in walking distance. Definitely will be back to stay again. Comes with a fully equipped kitchen and comfortable beds.

We stayed here for a long weekend getaway and it was the perfect, relaxing retreat! The space was comfortable, clean, and easily accessible. John was responsive and very polite. It is also super close to Hunter Mt so we would love to come back during ski season!

if you are looking for a modern updated place. look elsewhere. Susie's place is at least 200 years old, it is a farmhouse. creaky floors. and antique decors. it was very clean, had everything you need ( no TV, ok with us) and feeding the animals from the kitchen window made our trip worthwhile. Susie was a gem with a big heart who loves all her rescue animals and it showed. bring your boots, enjoy what this place has to offer, memories of a lifetime! we will be back!

This is the perfect location for a girl’s getaway. Being above a spa allows for convenient pampering, and we were pampered! We were celebrating a 60th birthday. Everyone loved our experiences at the Bodhi Spa, and downtown Hudson has so much fun that is all just a short walk away. Lots of great restaurants and lots of unique shops to enjoy! This was my third stay, and I’ll be back! The apartment is beautiful and the beds are cozy and the bathrooms are stocked with the Spa’s luxurious products! Treat yourself and your friends! ♥️

Super clean, beautiful space, and in the heart of Catskill main street! We were traveling with a toddler and the space worked well for us. Please note, you have to go up two flights of stairs to enter the unit.

We had a lovely stay at this charming townhouse in Hudson! The space is flooded with natural light, creating such a warm and inviting atmosphere throughout. It's impeccably clean, with every corner thoughtfully maintained. The bright, colorful art adds so much character and personality to the space! The amenities were top-notch, with everything we needed and more, including plenty of fresh linens. The location was also perfect, close to everything Hudson has to offer. Highly recommend this spot for anyone looking for a cozy, stylish, and comfortable getaway!

Our second lovely stay with Diana and Mark. Super clean place and great area. Only good things to say and can’t wait to go back.

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

I had an amazing stay! The home was spotless, beautifully decorated, and had everything I needed for a comfortable visit. The location was perfect—so close to Windham Ski Resort! Agnieszka was incredibly friendly and an excellent host. Highly recommend!

"Condo in Hunter" was a nice quiet getaway for my husband and me. Luiza was a good host- her place was clean, photos were accurate and it had all the listed amenities. She provided recommendations and communication was timely.

Cullen’s place was perfect for what we needed. We were in town for 2 nights, and we enjoyed our stay. The place was very clean, and the kitchen had everything you would need to use for meals. We would definitely book again!

Great 3rd floor walk up with Views of the mountain. The Room is in a historic building built by the Carnegy's in the 1800's if I remember correctly. It was perfect for what I needed. I got in late and they were very flexible with check out

Place was just as described and very cozy. It was also decorated for Christmas which was a nice touch. Kitchen fully stocked with all amenities you need and bed provided a nice sleep. While the unit is just steps away from ski in/out this was not the case for our trip in mid Dec as not all trails were open. This was not a huge inconvenience as the drive to park at the ski lodge is less than 5 mins.

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~

We had a lovely last minute stay. Perfect for our family, 8 and 5 year old kids. Lots of games and puzzles. Comfortable beds, and kitchen well stocked. Clean and great location.