Kid-friendly vacation rentals in Windham

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Windham kid-friendly rentals

Kid-friendly house rentals

Guest favorite
Home in Saugerties
4.94 out of 5 average rating, 68 reviews

Perfect Family Retreat•Pool•Volleyball•Firepit

YuliaRating, 5 stars2 months ago
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!
Guest favorite
A wooden playset is situated in a grassy area, featuring a slide, climbing wall, and a shaded awning. Sunlight filters through the surrounding trees, creating a bright and inviting space for outdoor play.
Home in Cornwallville
4.93 out of 5 average rating, 44 reviews

LOW Cleaning Fee! Family friendly with swing set

StephenRating, 5 stars6 months ago
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!
Guest favorite
Home in Phoenicia
4.96 out of 5 average rating, 154 reviews

Hiking and Breweries! Mountain and river views!

DallasRating, 5 stars1 week ago
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!
Superhost
Home in Ulster Park
4.88 out of 5 average rating, 227 reviews

Entire lake house to yourself. Great for groups

Maggie FuentesRating, 5 stars5 days ago
Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!
Guest favorite
The exterior of a renovated farmhouse is featured, surrounded by vibrant flower gardens. A stone wall borders the property, and the light green facade of the house is complemented by blooming red and yellow flowers, creating a serene countryside atmosphere.
Home in Pine Plains
5 out of 5 average rating, 15 reviews

Stony Hill Haus in Pine Plains

StaceyRating, 5 stars3 days ago
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.
Top guest favorite
A wooden playground structure is equipped with a blue slide, climbing wall, and two swings. The setting features a grassy area surrounded by trees with autumn leaves, providing a serene outdoor space for children to play.
Home in Saugerties
4.98 out of 5 average rating, 48 reviews

A Perfect Upstate Family Getaway with a Pool

DanaRating, 5 stars2 months ago
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.
Top guest favorite
A living room features a leather sofa and a wooden coffee table, surrounded by colorful artwork on the walls. Natural light fills the space through two windows, revealing a warm wood ceiling. A rocking chair and patterned rug add comfort to the inviting atmosphere.
Home in Woodstock
4.98 out of 5 average rating, 219 reviews

Sweeping mountain views in Woodstock, NY

DanielRating, 5 stars1 month ago
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.
Guest favorite
An open-plan kitchen and dining area is presented, featuring a large wooden dining table surrounded by turquoise chairs. Natural light filters through multiple windows, illuminating the space. The kitchen, equipped with modern appliances, complements the inviting, wood-paneled design.
Home in Livingston Manor
4.96 out of 5 average rating, 229 reviews

Wooded Livingston Manor Oasis With Stream & Deck

EmilsisRating, 5 stars5 months ago
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!

Kid-friendly apartment rentals

Guest favorite
A gravel driveway winds through a well-maintained yard, leading towards distant mountains under a clear blue sky. Sparse trees and an American flag add to the serene landscape, indicating a peaceful outdoor setting.
Apartment in Halcott Center
4.97 out of 5 average rating, 140 reviews

Mountain View Apartment

EricaRating, 5 stars3 months ago
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!!
Top guest favorite
A vibrant green sofa is adorned with a variety of colorful cushions, creating an engaging seating area. A modern lamp provides soft illumination, while a circular dining table with orange chairs is positioned nearby. Unique wall art pieces add character to the space.
Apartment in Hudson
4.98 out of 5 average rating, 175 reviews

Lower Warren Street Picture-Perfect 2-Bedroom Apt

LaurenRating, 5 stars1 week ago
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!
Guest favorite
A bright and airy bedroom is showcased, featuring a spacious bed with soft white linens. Two large windows with light curtains allow natural light to fill the room. A mirrored wall decor adds depth, while a stylish chair complements the cozy ambiance.
Apartment in Hudson
4.93 out of 5 average rating, 286 reviews

Chic Hudson Apartment - In the heart of Hudson, NY

DyeemahRating, 5 stars2 weeks ago
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!
Guest favorite
A bright and inviting living area features a gray sofa adorned with patterned throw pillows. A colorful wall sign adds character, while two orange lamp stands provide warm lighting. The space is framed by an open entryway leading to a visible hallway.
Apartment in Hudson
4.9 out of 5 average rating, 167 reviews

Private 1BR Apartment 1 Block from Warren St.

JamieRating, 5 stars1 week ago
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!
Superhost
The backyard features a landscaped area with green grass, equipped with comfortable seating and a picnic table shaded by umbrellas. Surrounding plants and sunflowers add color, while a garden area showcases fresh greenery. A rustic fence borders the space for added privacy.
Apartment in Kingston
4.82 out of 5 average rating, 108 reviews

2 bedroom / Office - HEPA Air Purifier

SarahRating, 5 stars4 months ago
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.
Guest favorite
A dining area showcases a round wooden table set with dishes and glasses, accompanied by green chairs. A cozy sofa and an armchair are positioned against the wall, while light streams through large windows, illuminating the warm wood flooring.
Apartment in Catskill
4.96 out of 5 average rating, 256 reviews

Above SpringRise

LizRating, 5 stars6 days ago
Perfect spot for a weekend in Catskill. I loved the ability to walk to local spots. So many things to do in the area if you like good food, drinks and a nice hike.
Top guest favorite
A comfortable seating area is highlighted by a modern chair beside a small side table. A decorative lamp illuminates the space, while artwork depicting greenery adorns the wall. Natural light filters in through the window, offering a view of the peaceful woods outside.
Apartment in Tillson
4.97 out of 5 average rating, 115 reviews

Woodland Neighborhood Retreat

YilinRating, 5 stars6 days ago
Great place to stay for exploring the New Paltz / Kingston area, loved how clean everything was! Lisa is a great host and provided super clear instructions.
Superhost
An eat-in kitchen is displayed with a large wooden dining table surrounded by four wooden chairs. The kitchen features white cabinets, a vintage clock, and large windows allowing natural light. Original beams support the 14-foot ceiling, and decorative tiles adorn the floor.
Apartment in Hudson
4.92 out of 5 average rating, 103 reviews

Sunny, Spacious & Central: Bowler

JacquelineRating, 5 stars1 week ago
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.

Kid-friendly condo rentals

Guest favorite
A multi-level chalet-style building features a blend of wood and stone exteriors. Large windows enhance natural light, and several balconies overlook a lush green landscape. A wooden bridge leads across a small waterway, connecting seamlessly to the surrounding nature.
Condo in West Kill
4.86 out of 5 average rating, 138 reviews

Trailside At Hunter-Phase II-Hunter NY

MengqiRating, 5 stars6 months ago
This condo is absolutely beautiful and comfy! We especially love the bed and pillows.
Guest favorite
A cozy living area features a light-colored sofa facing a decorative coffee table. A round rug with a nature motif complements the hardwood flooring. Large windows provide access to natural light, and a balcony can be glimpsed through the sliding glass door.
Condo in Windham
4.88 out of 5 average rating, 191 reviews

Cozy Mountain hideaway Windham, Hunter

RandolphRating, 5 stars2 weeks ago
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!
Top guest favorite
A cozy living room area features a dark leather sofa adorned with decorative pillows. Two lamps light the space, complemented by an ornate side table and a marble coffee table. A large piece of wall art enhances the inviting atmosphere, while a rich area rug covers the wooden floor.
Condo in Hunter
4.96 out of 5 average rating, 251 reviews

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

CaitlinRating, 5 stars2 months ago
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!
Guest favorite
A welcoming living area features a brown leather sofa with decorative pillows, a wooden coffee table, and a comfortable armchair. Soft lighting is provided by a floor lamp and a wall-mounted lamp. A sliding glass door leads to an outdoor deck surrounded by trees.
Condo in Windham
4.83 out of 5 average rating, 12 reviews

Windham-Hunter Lodge

MariaRating, 5 stars3 months ago
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.
Superhost
A wooden balcony features two adirondack chairs in bright green and blue, positioned for views of the surrounding mountains and tree-filled landscape. The clear sky and vibrant greenery create a serene outdoor space, perfect for relaxation.
Condo in Windham
4.81 out of 5 average rating, 138 reviews

Studio 3 BEDS-SLEEP 4

JeffRating, 5 stars2 months ago
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.
Superhost
The exterior of a two-story, wooden condo is visible, featuring a warm brown facade. A covered entrance with an American flag hangs beside the stairs leads up to the unit. Lush greenery and decorative shrubs enhance the inviting surroundings.
Condo in Windham
4.72 out of 5 average rating, 275 reviews

Summer Retreat w/ Balcony & inground Pool

RachelRating, 5 stars1 week ago
We loved staying here for the second time! thank you!
Top guest favorite
A modern living area features a dark blue sofa and a coffee table with decorative items. The open kitchen showcases stainless steel appliances and a dining area with four bar stools. Warm lighting enhances the inviting space, while wall art adds character.
Condo in Lanesville
4.97 out of 5 average rating, 630 reviews

Stylish Condo Hunter Mountain

Tianna JoanneRating, 5 stars1 week ago
The place was exactly as described and she was really attentive if I had sent a message and it was extremely clean and cozy.
Superhost
An open kitchen and living area is highlighted by natural light from large windows. A compact dining table for four is situated under a pendant light. Red cabinets offer a pop of color against yellow accents in the kitchen, with a cozy seating area featuring a textured rug.
Condo in Kingston
4.92 out of 5 average rating, 141 reviews

Cozy & walking distance to cafés *spring avails*

CateRating, 5 stars1 month ago
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.

Quick stats about vacation rentals that are kid-friendly in Windham

  • Total rentals

    60 properties

  • Nightly prices starting at

    $110 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

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Greene County
  5. Windham
  6. Kid-friendly rentals