Family-friendly holiday rentals in Windham

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Windham

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Home in Durham

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 favourite

Home in Windham

4.99 out of 5 average rating, 371 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 :)

Guest favourite

Condo in Windham

4.89 out of 5 average rating, 206 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.

Top Guest favourite

Home in Windham

4.94 out of 5 average rating, 101 reviews

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

A unique blend of architectural and design features, this home is one of a kind and perfect for your mountain getaway. The expansive 3800+ sq ft mountain retreat features 5 bedrooms, 5.5 bathrooms, and two large living areas, providing plenty of space to accommodate family & friends. There is also a brand new speakeasy bar to enjoy. Steps to the ski trail (or mountain biking) and hiking, golf, restaurants, and wedding venues, the location is ideal for all seasons. @AlpineLookout on IG

Guest favourite

Home in Hunter

4.96 out of 5 average rating, 159 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 favourite

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 favourite

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.

Guest favourite

Cabin in Windham

4.95 out of 5 average rating, 139 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.

Top Guest favourite

Townhouse in Windham

4.9 out of 5 average rating, 122 reviews

Windham Mountain Village 2 bedroom townhouse

This 2 bedroom, 2 bath Townhouse with loft that sleeps 8 (max 6 adults) is located at the top of Windham Mt Village a very short walking distance from the Windham ski lodge and beginner lifts. Fully equipped kitchen, dining area, living area with fireplace including firewood. TV with cable and free high speed wifi. Outdoor deck with gas grill. Washer and Dryer. 2 parking spots in front. Access to community pool and hot tub when open. Air Conditioning in summer.

Superhost

Condo in Windham

4.73 out of 5 average rating, 285 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!

Top Guest favourite

Cabin in Windham

4.97 out of 5 average rating, 107 reviews

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing pond and a deck offering panoramic resort views, it's a perfect outdoor retreat. Inside, enjoy a pool table, Pac-Man arcade, and shuffleboard for endless fun. A 2-minute drive to town makes dining and shopping convenient. The cabin's modern amenities, cozy fireplace, outdoor firepit, and hot tub guarantee a comfortable and relaxing stay.

Top Guest favourite

Home in Windham

4.93 out of 5 average rating, 119 reviews

Big Red Retreat 3 min to Windham Mountain & Golf!

Welcome to Big Red – Your Ultimate Mountain Retreat! Nestled in the heart of the scenic Windham area, Big Red invites you to experience the perfect blend of comfort, convenience, and adventure. Whether you're here to hit the slopes at Windham Mountain, explore the tranquil Windham Path, or tee off at the nearby golf course, our spacious 6-bedroom, 2.5-bath home is your ideal basecamp for an unforgettable getaway.