We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Family-friendly vacation 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.

0 of 0 items showing

1 of 3 pages

Cabin in Maplecrest

4.95 out of 5 average rating, 202 reviews

The Cabin - Ski House near Windham

The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

Townhouse in Windham

4.93 out of 5 average rating, 113 reviews

1 minute to skiing,hot tub firepit cornhole & pond

Red FoxTownhouse & amazing Alpine Hot Tub Spa Bathrobes & slippers provided Beautiful 2 bedroom & 2 full bathroom townhome Well-stocked kitchen & appliances FREE Coffee provided for the MR. Coffee unit Large screen Smart TV in living room Large Rock Fire-pit-firewood provided Weber BBQ grill-tools & propane tank On property walking trail to the pond with 2 kayaks (seasonal) Walking distance to the Chicken Run Restaurant & Bar The homeowners reside on the premises in the adjacent townhouse

Home in Windham

4.99 out of 5 average rating, 347 reviews

Custom-built Catskills 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 :)

Townhouse in Windham

4.83 out of 5 average rating, 189 reviews

Redwood Retreat in Windham - Minutes to Mntn!

True mountain getaway, just 2.5 hours from NYC!! Spacious 2 bedroom 2 bathroom townhouse minutes to Windham Mountain. Enjoy beautiful wood-burning fireplace, Roku TV and high speed Wi-Fi perfect for remote work. Amenities include outdoor pool (open from Memorial through Labor Day), pickleball, basketball and tennis courts, as well as a fire pit with Adirondack chairs. Very close to town and the amazing escarpment hiking and Elm Ridge mountain bike trails. NOW OPEN FOR 2024/25 SKI SEASON!!

Cabin in Windham

4.93 out of 5 average rating, 406 reviews

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)

At face value, IG: @cozycatskillchalet appears to be just a humble little getaway tucked in the Catksill Mountains of Windham, NY. But even the most discerning guests will be quickly spirited away by the rustic charm and postcard-eqsue surroundings all around. At night, can't-be-beat stargazing on the back deck (or while soaking in the hot tub) will have you convinced this humble hideaway is a lot more illustrious than it lets on. Disclaimer: The chalet is not a luxury hotel or property.

Chalet in Windham

4.96 out of 5 average rating, 119 reviews

Beautiful Windham Chalet 2 minutes to the Mountain

Beautiful Chalet close to Skiing, snowboarding, sledding, snowshoeing, mountain biking, hiking, golfing, wine tasting, zip lining, Windham and Hunter Mountain festivals, great restaurants, and more. Relax on the beautiful deck while taking in the mountain views or cozy up to the fire pit. Enjoy a Gorgeous modern kitchen, fireplace and wood burning stove. All amenities including washer, dryer, dishwasher, microwave, coffeemaker, BBQ, and paper products. Free WiFi. Sleeps 11. Pet friendly.

Condo in Windham

4.84 out of 5 average rating, 122 reviews

Studio 3 BEDS-SLEEP 4

Light-filled studio in downtown Windham. Beautiful mountain views from your balcony; at night gaze at the moon & stars If you want solitude, this is the place to be! Daytime, take a walk down to the river & enjoy! Walking distance to restaurants & small grocery. Studio is big, with closet, full bathroom, well-stocked coffee area with microwave and refrigerator. Maximum 3 people; 1 double & 2 twins. Check-in: From 4PM off-street parking, Free Wifi /Basic Cable /Linens/Coffee

Cabin in Gilboa

4.86 out of 5 average rating, 165 reviews

🌟Cozy Cabin-Catskills secluded Mountain retreat🌟

A true Catskill mountain private cabin experience. Tucked away in the woods w/ everything you need Wifi, Fireplace,Full kitchen, Plush Queen bed in the master and another queen and futon in the loft, Bluetooth speakers in & out, , A/C and heat unit. BBQ grill and outdoor fire pit, Smart TV, Google Home, Vehicle with AWD may be needed to get down driveway in the winter or late fall. Firewood avail. Pets welcome with a fee. 25 min to Windham mountain ski.

Home in Jewett

4.96 out of 5 average rating, 164 reviews

Mountain house w/ Scandinavian BBQ hut Spa & more!

Private yet 5 minutes away from the quaint town of Windham and eight minutes to Hunter our house sits on 5 acres of beautiful land. Recently renovated with fully equipped kitchen that awaits your magical chef touch, comfortable bedrooms provide restful sleep , sparkling and airy bathrooms and cozy , relaxing living room. Wake up to the song of birds, sip a coffee on the deck take a hike and leave your worries behind.

Cabin in Jefferson

5 out of 5 average rating, 462 reviews

"Far from the Madding Crowd" Cozy Cabin Retreat

Cabin Clack is a quiet, stream-side retreat bordering 1000 acres of wild trails in NY State Forest. The cabin is a historic hunting cabin from circa 1935. The cabin is good for a couple, solo adventurers, or families (with kids). We welcome pets, and they will love exploring the secluded forest and the freedom of our virtually traffic-free dead-end road. There is a spring fed pond you can swim in.

Cabin in Cornwallville

4.97 out of 5 average rating, 535 reviews

The Log Cabin in the Catskills

"This Catskills log cabin is a true upstate beauty, a seamless blend of rusticity and modernity" - Time Out Magazine "Best Cabins to Rent Across the Country" Offering a retreat to the forests of The Great Northern Catskills, encouraging a return to Nature. Visit our site, Catskill & Co dot com to learn more about us, to see suggestions on all that is Nearby, and to shop The Cabin Collection!

Rental unit in Jewett

4.8 out of 5 average rating, 184 reviews

Cozy Retreat in the Catskills

Cozy walk-in one bedroom apartment in the lower level of our home. Full kitchen, full size bed in bedroom, living room w/ pullout couch, WiFi, and private bathroom. Great location between Hunter and Windham Mountains, just 5 miles to either resort. Beautiful secluded location surrounded by mountains and forest.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Chalets

Adventure-ready homes with après-ski style

Hotels

Stylish accommodations and amenities

Popular amenities for Windham family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Windham

4.88 out of 5 average rating, 129 reviews

Live the Slow Life at an All-Season Mountain Escape

Home in Craryville

4.98 out of 5 average rating, 205 reviews

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson

Chalet in Jewett

4.97 out of 5 average rating, 173 reviews

Private Catskills Home w. Hot Tub, near Ski Mnt

Cabin in Mount Tremper

4.92 out of 5 average rating, 132 reviews

Luxury Woodstock Cabin in the Woods!

Cabin in Durham

4.91 out of 5 average rating, 181 reviews

Coziest Catskills Cabin new huge trex deck+hottub

Home in Windham

4.95 out of 5 average rating, 110 reviews

Charming Home Lg/Mod Kit Hot Tub on Stream FirePit

Cottage in Greenville

4.92 out of 5 average rating, 211 reviews

Historic farmhouse escape on 14 scenic acres

Home in Roxbury

4.99 out of 5 average rating, 233 reviews

Charming Cottage on 12 Secluded Acres + Hot Tub

Family- and pet-friendly home rentals

Cabin in Boiceville

4.98 out of 5 average rating, 475 reviews

Winston's Place - Woodland Cozy Catskills Cabin

Barn in Woodstock

4.83 out of 5 average rating, 187 reviews

The Woodstock Barn Studio

Home in Palenville

4.95 out of 5 average rating, 125 reviews

Serenity Retreat: Mountains, Waterfalls, Comfort

Home in West Fulton

4.9 out of 5 average rating, 126 reviews

Beautiful Farm Cottage & Majestic Waterfall

Cabin in Arkville

4.97 out of 5 average rating, 312 reviews

Solace: perfect for all seasons; near Belleayre Mt

Cottage in Halcott Center

4.97 out of 5 average rating, 291 reviews

Cozy Cottage with Stunning Mountain Views

Cabin in Woodstock

4.93 out of 5 average rating, 688 reviews

Byrdcliffe Artist Studio (27.1-1-70)

Home in Hunter

4.96 out of 5 average rating, 242 reviews

View Hunter mountain House

Family-friendly home rentals with a pool

Home in Woodstock

4.89 out of 5 average rating, 157 reviews

The Shula | Farmhouse | Fire pit, Hot tub, Pool

Home in Mount Tremper

4.93 out of 5 average rating, 200 reviews

Zen, Modern, Glass - Indoors meets Outdoors

Rental unit in Earlton

4.93 out of 5 average rating, 290 reviews

Sweet Farm Stay

Home in Ghent

4.88 out of 5 average rating, 302 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Home in Saugerties

4.96 out of 5 average rating, 160 reviews

Lux 1800's renovated farmhouse w/hot tub+pool

Cabin in Red Hook

4.96 out of 5 average rating, 337 reviews

Modern Upstate Cabin, near Rhinebeck NY

Home in woodstock

4.86 out of 5 average rating, 504 reviews

CABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN

Cabin in Prattsville

4.82 out of 5 average rating, 165 reviews

Private 6 acre w/Mountain Views; POND & HOT TUB!

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

Total rentals
140 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
4.9K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Destinations to explore