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Kid-friendly vacation rentals in Windham

Find and book unique kid-friendly rentals on Airbnb

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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Top guest favorite

An open floor plan living area features vaulted wooden ceilings and large windows offering views of the outdoors. Comfortable seating areas include a tan couch, black chairs, and a decorative coffee table. A dining space with a large table and an island kitchen is also visible.

Chalet in Windham

4.98 out of 5 average rating, 138 reviews

Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing

Plan your all-seasons escape to this gorgeous new mid-century modern chalet with can't-beat direct views of Windham Mtn, less than a 5 minute drive away. Situated between state land and an active creek, enjoy this mountain getaway's hot tub, firepit, game room, open floor plan and other luxury amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

The open living area features elevated ceilings with wooden beams and large windows flooding the space with natural light. A wood-burning fireplace is positioned beneath a wall-mounted TV, flanked by two rocking chairs and a circular coffee table set on a textured area rug.

Townhouse in Windham

4.95 out of 5 average rating, 101 reviews

Lothbrok - the "B" side - 2 mile slopes & town

5 min to Windham Mountain / easy 15-19 min to Hunter! 1 mile to Windham's Main Street - restaurants, pubs, movie theatre & shopping. Remodeled with luxury vinyl flooring, low VOC paint, LED lighting, Culligan water treatment, excellent cell phone service & FREE WiFi means no issues making calls/texts/internet. We kept some of the groovy charm of the 1970's (spiral stairs) and brought the house into this century looking brand new again. NOT SAFE for babies, children under 12 or pets. No smoking.

A peaceful outdoor setting features several white Adirondack chairs arranged around a campfire-style fire pit. Lush green grass and trees frame the scene, while distant mountains and a blue sky with clouds create a serene backdrop.

4.96 out of 5 average rating, 134 reviews

Wow! Panoramic Mountain View, Minutes to Windham!

This pristinely-kept vacation home has endless mountain views on rolling country acres. Come and stay just to get away, enjoy both the sunrise and sunset views from the expansive deck. Curl up by the wood burning fireplace or the outdoor fire-pit, or take a sunset plunge in our backyard hottub and enjoy the picturesque views of Windham, NY from across the valley. A serene 8 mile drive will take you into the historic Town of Windham, NY to enjoy a day of skiing, site-seeing, hiking or dining

Top guest favorite

The log-built chalet is surrounded by lush greenery and rolling hills. A spacious porch wraps around the house, and a fire pit with seating is visible in the foreground, providing a welcoming outdoor space amidst the natural landscape.

Chalet in Gilboa

4.98 out of 5 average rating, 162 reviews

Secluded Chalet w/ Unforgettable Views on 22 Acres

A nature-lover's oasis, this 3-bedroom/4-bed/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 22+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

A cozy bedroom features a spacious bed with a patterned quilt. Bright natural light fills the room through large windows, complemented by soft window treatments. A comfortable chair, wooden dresser, and wall-mounted television add to the inviting space's functionality and warmth.

Townhouse in Windham

4.89 out of 5 average rating, 150 reviews

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

Top guest favorite

The exterior of a charming A-frame house is depicted under a dusk sky, adorned with warm lights that outline the roof. A welcome sign is displayed beside a green front door, which is enhanced by a decorative wreath. Soft landscaping and pathway lighting create a cozy ambiance.

Home in Windham

4.99 out of 5 average rating, 368 reviews

Custom Catskills private retreat

This is a 2 bedroom 1 bath house located just 7 minutes from the Windham ski mountain. The house is surrounded by scenic land with few neighbors to be seen. Skiing, fall foliage, swimming holes, hiking, golf, antiquing, horseback riding, local farms are just a few things to name that this area has to offer. The house itself is a true retreat, you will leave totally re-charged - sweet air, bird chirping, star gazing, grilling, bong fire or simply enjoy a few days of not seeing another soul :)

An outdoor pool is surrounded by a spacious deck with multiple lounge chairs positioned for relaxation. Lush greenery forms a serene backdrop, while a set of steps leads into the clear water. A shaded area is visible to the side, enhancing the tranquil setting.

Condo in Windham

4.89 out of 5 average rating, 202 reviews

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.

4.96 out of 5 average rating, 156 reviews

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Top guest favorite

The chalet stands amidst vibrant autumn foliage, showcasing a green exterior and a spacious deck. The well-maintained yard features a lush green lawn, with a variety of trees surrounding the property that enhance the natural setting.

Guesthouse in Windham

4.99 out of 5 average rating, 167 reviews

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

Top guest favorite

The two-story black house is surrounded by trees, showcasing a spacious outdoor deck lit with string lights. A hot tub is visible to the side, with stairs leading up to the entrance. The serene landscape offers a calming retreat atmosphere.

Cabin in Windham

4.97 out of 5 average rating, 124 reviews

Casa Magda - Designer Home near Hiking + Swimming

Relax and recharge at Casa Magda—a design-inspiring home on 9 acres in Windham, NY—just 2.5 hrs north of NYC! For design lovers and nature seekers, this 1980s gem has been redesigned with modern flair and offers serene solitude. Relax by the hot tub, cozy up by the fireplace with a record and lounge around the campfire to view stellar constellations and the Milky Way. Explore nearby eateries and hikes. Ski the Windham slopes within a 7 min drive, or head to Hunter in 15 mins.

The cabin is set in a lush green landscape, surrounded by trees. A spacious deck features outdoor seating, while a fire pit is situated within a circle of chairs, inviting gatherings. The facade displays large windows, enhancing the connection to nature.

Cabin in Windham

4.95 out of 5 average rating, 138 reviews

The Creekside Cabin - 5 mins to Windham Mt!

Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.

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, 283 reviews

Summer Retreat w/ Balcony & inground Pool

Leave your worries at home and come relax in our newly renovated, one bedroom condo in the heart of the Catskills. welcome to our end unit,features wood burning fireplace, king size bed, balcony overlooking the grounds and into the woods, includes 2 tennis courts, WiFi and is only minutes away from Windham and Hunter Mountain! Come enjoy all year round with hiking, mountain biking, kayaking, zip lining, snowboarding and skiing! **POOL OPENS MEMORIAL DAY 2023!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for Windham kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

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

Top guest favorite

A striking mountain retreat is framed by snow-covered landscaping and wooden railings. The entrance features a stone facade and a charming balcony, with the warm wooden roofline extending above. Tall trees provide a natural backdrop, creating a serene winter scene.

Home in Windham

4.94 out of 5 average rating, 101 reviews

Stay on Windham Mt- Mins to Main St + Hot Tub

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

4.93 out of 5 average rating, 118 reviews

Big Red Retreat 3 min to Windham Mountain & Golf!

Top guest favorite

The farmhouse exterior features a spacious porch with steps leading down to a grassy area. The surrounding landscape includes trees, providing a natural setting. Large windows allow for plenty of natural light, enhancing the home's open feel.

Home in Saugerties

4.92 out of 5 average rating, 256 reviews

Beautiful farmhouse with Mountain View- HITS- AC

A charming gray house is set against a lush green landscape, featuring an inviting front door. A serene pond reflects the blue sky and surrounding trees, creating a peaceful atmosphere. Comfortable seating arrangements are visible near a hot tub, offering a space for relaxation while enjoying the outdoors.

Home in Prattsville

4.94 out of 5 average rating, 134 reviews

10acres Catskill Mntn vws, hot tub, fire pit, pond

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, 243 reviews

Modern Ski-Home With Views Near Hunter & Windham

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

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, 249 reviews

Bluff House

Kid-friendly apartment rentals

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, 143 reviews

Mountain View Apartment

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, 297 reviews

"Your Country Getaway at Beulah Land Farm."

The living room features a light-colored sofa adorned with assorted pillows, positioned next to large windows that invite natural light. A vibrant area rug adds warmth to the wooden floor. Decorative plants and a framed piece of art contribute to the inviting atmosphere.

Apartment in Hudson

4.98 out of 5 average rating, 257 reviews

Serving Sexy Historic Hudson Realness Steps from Warren St

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, 153 reviews

Susie's Climax Creations

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

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, 182 reviews

Catskill Village House - The Loft

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

4.81 out of 5 average rating, 190 reviews

Cozy Retreat in the Catskills

Top guest favorite

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

5 out of 5 average rating, 121 reviews

Hudson River Beach House

Kid-friendly condo rentals

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

A spacious outdoor deck is visible, furnished with a round table surrounded by several chairs and a lantern on top. A comfortable seating area with a couch is positioned nearby, set against a backdrop of lush greenery.

Condo in Windham

4.67 out of 5 average rating, 117 reviews

Windham Condo

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, 252 reviews

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

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!

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, 139 reviews

Studio 3 BEDS-SLEEP 4

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, 643 reviews

Stylish Condo Hunter Mountain

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, 148 reviews

Cozy & walking distance to town *summer/fall dates

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, 508 reviews

*Great Reviews* Hunter Mtn. Clean Close Cozy Condo

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
3K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

Destinations to explore