
Kid-friendly vacation rentals in Windham
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Top-rated kid-friendly rentals in Windham
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Windham kid-friendly rentals
Kid-friendly house rentals

Catskills Retreat: Hot Tub | Fireplace | Firepit
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!!

Big Red Retreat 3 min to Windham Mountain & Golf!
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!

Zen Cottage retreat to nature
We stayed for a few days at the zen cottage and it was the most relaxing and peaceful weekend. The cottage is exactly has described and super clean. Alma and James were very helpful and welcoming. Overall had an extremely enjoyable weekend and hope to come back soon

“Spectacular Mountain Views with Tranquility”
Beautiful home! Very convenient to Windham mountain/town. We would definitely stay again

Modern Ski-Home With Views Near Hunter & Windham
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.

Mountain and tree view cabin on 12 private acres
The view is everything!! A great weekend getaway

Bluff House
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!

Private Waterfall Retreat on 10 acres
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!
Kid-friendly apartment rentals

Mountain View Apartment
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!

"Your Country Getaway at Beulah Land Farm."
We had a lovely stay here. The apartment was spotless, well stocked and comfortable. It suited our needs for a location in the Catskills.

Susie's Climax Creations
I truly enjoyed my stay at Susie's place. She was extremely welcoming, warm, and friendly. I loved having a place to stay right on the farm. My dog loved exploring and smelling all around the property. The rooms were spotless and very comfortable. I slept really well. All the animals were wonderful and I loved hearing their stories and having a change of scene from what I do day-to-day. This place and this stay was just what I needed. Easy access to nearby cute towns like Coxsackie, Hudson, and Catskill. I would love to come back again in the future. And I would definitely recommend this place to others.

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

Burnt Knob Mountain Escape
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.

Catskill Village House - The Loft
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!

Cozy Retreat in the Catskills
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!

Newly Renovated Apt. Mins from Warren St.
The apartment was very cozy and homey, plus very clean. It's perfect for a weekend getaway in Hudson. Great access to all the best restaurants and shops that Hudson has to offer.
Kid-friendly condo rentals

Trailside At Hunter-Phase II-Hunter NY
This condo is absolutely beautiful and comfy! We especially love the bed and pillows.

Mountainside Haven
The location was very peaceful and comfortable. It has a great view of the mountains in the background. The place had everything you needed and was very clean and had cabin like qualities. Very beautiful inside and outside as well. The host was very kind and responded right away to any questions I had.

Mint*Cozy*Ski In/Out*Hunter Mt Condo w/Fireplace
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!

Cozy condo in Windham - Near Everything!
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.

Studio 3 BEDS-SLEEP 4
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.

Cozy & walking distance to cafés *spring avails*
Cozy apartment, walking distance from the water front. Had a great weekend getaway.

4.Special long term prices - escape the City!
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 Reviews* Hunter Mtn. Cozy Clean Close Condo
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!
Quick stats about vacation rentals that are kid-friendly in Windham
Total rentals
60 properties
Nightly prices starting at
ﺩ.ﺇ404 before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- Glimmerglass State Park
- John Boyd Thacher State Park
- Windham Mountain
- Resorts World Catskills
- Albany Center Gallery
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Walkway Over the Hudson State Historic Park
- Zoom Flume
- Hunter Mountain Resort
- Norman Rockwell Museum
- Hancock Shaker Village
- Opus 40
- Naumkeag
- Pineridge Cross Country Ski Area
- Thaddeus Hait Farm
- Butternut Ski Area and Tubing Center
- Berkshire Botanical Garden