Kid-friendly vacation rentals in Windham

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Popular amenities for Windham kid-friendly rentals

Kid-friendly house rentals

Guest favorite
A cozy living room features a stone fireplace as the focal point, complemented by large windows that offer views of the outdoor deck. A wooden coffee table is surrounded by wicker chairs, and a decorative plant adds a touch of greenery.
Home in Windham
4.88 out of 5 average rating, 136 reviews

Catskills Retreat: Hot Tub | Fireplace | Firepit

LukeRating, 5 stars3 months ago
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!!
Top guest favorite
The image displays a charming red house with two stories, featuring a welcoming front porch with white railings. A snow-covered yard surrounds the home, while a large tree is positioned to the left. The clear blue sky adds to the serene atmosphere.
Home in Windham
4.95 out of 5 average rating, 112 reviews

Big Red Retreat 3 min to Windham Mountain & Golf!

NancyRating, 5 stars2 months ago
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!
Guest favorite
The cottage features a white exterior with green shutters and a metal roof. A pathway lined with flowers leads to the entrance. A white picket fence surrounds the front yard, enhancing the cottage's inviting curb appeal.
Home in Phoenicia
4.94 out of 5 average rating, 583 reviews

Zen Cottage retreat to nature

AvaRating, 5 stars1 week ago
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
Top guest favorite
A spacious great room features large windows allowing natural light to fill the space, offering views of surrounding trees. A comfortable sofa and leather chair provide seating, while a wooden coffee table sits at the center. A stone fireplace adds a focal point to the room.
Home in Windham
4.99 out of 5 average rating, 107 reviews

“Spectacular Mountain Views with Tranquility”

DanielleRating, 5 stars3 months ago
Beautiful home! Very convenient to Windham mountain/town. We would definitely stay again
Guest favorite
An open living space features a modern design with skylights and large windows providing natural light. A stone fireplace is situated near the seating area, which is complemented by a dining table and chairs. Warm wooden flooring adds to the inviting ambiance.
Home in East Jewett
4.98 out of 5 average rating, 240 reviews

Modern Ski-Home With Views Near Hunter & Windham

CaroRating, 5 stars4 weeks ago
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.
Top guest favorite
The rustic cabin features a sloped green metal roof and a spacious wooden deck, surrounded by well-maintained gardens with colorful flowers. Lush trees provide a natural backdrop, enhancing the peaceful setting of the 12-acre property.
Home in Roxbury
4.97 out of 5 average rating, 126 reviews

Mountain and tree view cabin on 12 private acres

LinmarieRating, 5 stars2 weeks ago
The view is everything!! A great weekend getaway
Guest favorite
The spacious living and dining area features a fieldstone fireplace as a focal point. Exposed beams add character, while colorful hanging lamps brighten the space. A large wooden dining table is surrounded by sleek chairs, and cozy seating areas are arranged for relaxation.
Home in East Durham
4.93 out of 5 average rating, 248 reviews

Bluff House

ChuckRating, 5 stars2 weeks ago
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!
Top guest favorite
A modern kitchen features natural wood cabinetry and shelves adorned with an array of dishes and glassware. A window above the sink offers a view of the outdoors, while warm wood paneling accentuates the ceiling.
Home in Cornwallville
4.99 out of 5 average rating, 144 reviews

Private Waterfall Retreat on 10 acres

AlannaRating, 5 stars3 weeks ago
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

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, 141 reviews

Mountain View Apartment

IrynaRating, 5 stars2 weeks ago
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!
Top guest favorite
The exterior of a charming farmhouse is captured, showcasing a green facade with white trim and a red roof. A spacious porch can be seen, providing an inviting entrance. Surrounding grassy areas and trees complement the rural setting, illuminated by natural sunlight.
Apartment in Roxbury
4.94 out of 5 average rating, 289 reviews

"Your Country Getaway at Beulah Land Farm."

LisaRating, 5 stars2 weeks ago
We had a lovely stay here. The apartment was spotless, well stocked and comfortable. It suited our needs for a location in the Catskills.
Top guest favorite
A friendly horse leans through an open window, with soft curtains framing its gentle face. The horse's striking black and white markings are visible, while light filters softly into the room, highlighting the welcoming ambiance.
Apartment in Coxsackie
4.97 out of 5 average rating, 148 reviews

Susie's Climax Creations

TeaganRating, 5 stars3 weeks ago
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.
Superhost
An airy interior showcases exposed wooden beams and a blend of modern and rustic decor. A kitchen counter with stools is positioned towards the left, complemented by a dining table with chairs in the center. A cozy bedroom is visible through the doorway on the right.
Apartment in Philmont
4.9 out of 5 average rating, 118 reviews

Beautiful space in the heart of Philmont

JessicaRating, 5 stars7 months ago
Wonderful stay! Beautiful home and so much to do in the area. We had a great time!
Top guest favorite
A vibrant sunrise casts shades of orange and yellow across the sky, illuminating the lush green landscape below. A serene pond is nestled within the meadow, surrounded by trees that display autumn colors, providing a tranquil setting for outdoor relaxation.
Apartment in Acra
4.99 out of 5 average rating, 157 reviews

Burnt Knob Mountain Escape

MatthewRating, 5 stars4 months ago
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.
Guest favorite
A cozy bedroom features a spacious bed with elegant grey bedding, complemented by unique wall art that mimics tree branches. Natural light filters in through wide windows under a slanted ceiling, while a stylish chair and nightstands add to the room's charm.
Apartment in Catskill
4.88 out of 5 average rating, 179 reviews

Catskill Village House - The Loft

GloRating, 5 stars3 weeks ago
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!
Guest favorite
A cozy living room is presented, featuring a classic patterned couch and a rocking chair. Natural light enters through two windows adorned with sheer curtains. A small writing desk is positioned near the entrance, and a vibrant area rug adds warmth to the hardwood floor.
Apartment in Jewett
4.8 out of 5 average rating, 188 reviews

Cozy Retreat in the Catskills

XuyangRating, 5 stars4 months ago
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!
Guest favorite
A spacious living area is highlighted by natural light entering through large windows. A deep blue sofa is centered, complemented by two armchairs and a wood console with a television. A small desk and potted plants add to the inviting ambiance.
Apartment in Hudson
4.95 out of 5 average rating, 204 reviews

Newly Renovated Apt. Mins from Warren St.

JackRating, 5 stars3 months ago
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

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 Hunter
4.86 out of 5 average rating, 138 reviews

Trailside At Hunter-Phase II-Hunter NY

MengqiRating, 5 stars7 months ago
This condo is absolutely beautiful and comfy! We especially love the bed and pillows.
Guest favorite
A living area features warm wood paneling and a comfortable leather couch. A flat-screen TV is positioned on a low wooden console. Soft lighting is provided by a standing lamp, while a door leads outside to a stone patio area, enhancing natural light in the space.
Condo in Hunter
4.96 out of 5 average rating, 23 reviews

Mountainside Haven

AndreaRating, 5 stars1 month ago
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.
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 stars3 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 comfortable living area is presented with a light-colored couch and armchair. A wooden coffee table is situated in front of the seating. A television is mounted on the wall, while natural light enters through the front door and window, enhancing the warm ambiance.
Condo in Hensonville
4.88 out of 5 average rating, 73 reviews

Cozy condo in Windham - Near Everything!

CarolynRating, 5 stars2 weeks ago
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.
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 stars3 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
A well-lit bedroom features a spacious bed with white linens and an accent pillow. Bright light streams in through two windows adorned with sheer curtains. A side table with a small lamp adds a touch of warmth to the inviting space.
Condo in Kingston
4.91 out of 5 average rating, 144 reviews

Cozy & walking distance to cafés *spring avails*

JananiRating, 5 stars2 months ago
Cozy apartment, walking distance from the water front. Had a great weekend getaway.
Guest favorite
A spacious living room is highlighted by two comfortable sofas and a lounge chair, arranged around a coffee table. A dining table for four is positioned near large windows, allowing natural light to fill the area. A flat-screen TV is mounted on the wall.
Condo in Windham
4.76 out of 5 average rating, 67 reviews

4.Special long term prices - escape the City!

ParmjitRating, 5 stars8 months ago
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.
Guest favorite
A studio condo features a cozy sleeping area with a patchwork quilt covering a spacious bed. A TV is positioned on a wooden dresser, while a red sectional couch is adorned with various patterned pillows. Ambient light enters through a window, creating a welcoming atmosphere.
Condo in Hunter
4.96 out of 5 average rating, 502 reviews

*Great Reviews* Hunter Mtn. Cozy Clean Close Condo

GerardoRating, 5 stars2 weeks ago
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

Destinations to explore

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