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.

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Guest favourite

Cottage in Lanesville

4.94 out of 5 average rating, 165 reviews

Creekfront Cottage between Phoenicia & Hunter Mtn.

Built in the Summer of 1929, Stony Clove Cottage is nestled in the woods on a beautiful mountain stream, the Stony Clove Creek. It is a magical place suited for folks ready to turn their phones off. In 2021, wifi was added to this once landline-locked retreat so guests can remotely work or study in the woods. Bluetooth speakers are outside, and a turntable, with albums ranging from Rodgers & Hammerstein to Laura Nyro to Ralph Stanley, is available inside. And a wall of movies. And books....

Nov. 14 – 21

$223 CAD per night

Superhost

Cabin in Maplecrest

4.95 out of 5 average rating, 173 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.

Oct. 10 – 17

$625 CAD per night

Guest favourite

Home in Windham

4.95 out of 5 average rating, 105 reviews

Charming Home Lg/Mod Kit Hot Tub on Stream FirePit

Beautiful Country setting, Large fire pit across bridge next to beautiful stream w 6 Adirondack chairs,new stream side bluestone patio.2.6 miles from Ski Windham. Modern spacious kitchen Wolf &Sub Zero , Breville Barista espresso machine, comfy living rm with pellet stove and 1906 antique player piano, flat screen smart TV. Large deck with stream view ,outdoor flat screen tv. Newly installed 6 Person Hot Tub w waterfall,2 person shower for relaxation after a hike. Gas fire table on deck also.

Nov. 2 – 9

$516 CAD per night

Guest favourite

Loft in Windham

4.97 out of 5 average rating, 101 reviews

The Windham Loft

This is a unique, modern, open-air loft apartment in Windham, NY conveniently located 1 mile from Windham Mountain Resort, seconds from the Wylder event venue, minutes from great mountain biking and across the street from the Windham Country Club golf course. The loft is spotlessly clean, welcoming and fun. You can't help but smile when you enter the space!! The Windham Loft is walking distance from several restaurants and bars and upstairs from a fabulous ski/bike shop and adjoining cafe.

Nov. 3 – 10

$282 CAD per night

Guest favourite

Chalet in Windham

4.97 out of 5 average rating, 115 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 w/Netflix. Sleeps 11. Pets ok.

Nov. 18 – 25

$486 CAD per night

Guest favourite

Townhouse in Hunter

4.91 out of 5 average rating, 136 reviews

Spring into a Dynamic Stay at an Ideal Hunter Home

Classic Townhome- w/ Classic feel. SPRING SPECIALS Centrally located spacious getaway with simple contemporary style with classic comfort w/ amazing views owned and operated by AIRBNB Super Host and NY Native. 2 min drive or a 15 min walk to Hunter Mtn. Next to the boutique Scribner Lodge and their amazing restaurant. Hiking, biking, BBQ & breathe in the views and enjoy 2 stone fireplaces OR the outdoor fire pit Bedroom A/C's. Great for a family getaway or few days out of town w/ friends.

May 6 – 13

$142 CAD per night

Guest favourite

Condo in Hunter

4.97 out of 5 average rating, 427 reviews

*Great Reviews* Hunter Mtn. Clean/Close/Cozy Condo

*Clean, cozy studio condo in the Village of Hunter featuring vintage decor. Short walk to the Ski Slopes, Snowtubing Park, Scenic Skyride, Dolan's Lake/Beach, Schoharie Creek, Fly Fishing, Hiking, Disc Golf, Stores, Eateries & Trailways Bus Stop. A Murphy bed w/ full size comfy Casper Mattress, a sectional couch, kitchen, microwave, electric wood stove, dinette, full bath, strong WiFi, Smart TV (no cable) w/Netflix, HBOGO, Pandora. No Pets/No Smoking or vaping in or on the property. Thanks

Jul. 15 – 22

$140 CAD per night

Guest favourite

Cabin in Windham

4.94 out of 5 average rating, 358 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.

Aug. 6 – 13

$783 CAD per night

Superhost

Condo in Windham

4.84 out of 5 average rating, 112 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

Jan. 17 – 24

$225 CAD per night

Guest favourite

Cabin in Chichester

4.99 out of 5 average rating, 514 reviews

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek

Aug. 19 – 26

$188 CAD per night

Guest favourite

Condo in Hunter

4.98 out of 5 average rating, 536 reviews

Hunter Mtn Liftside Ski In/Out, Slopeside!

Fantastic location! Liftside! Beautifully renovated SLOPESIDE ski on/ski off condo . Spacious one bedroom condo with fully stocked kitchen, luxurious bathroom with jacuzzi tub, large bedroom with queen bed, and comfortable, cozy open concept living and dining room. Real wood burning fireplace. Private deck backs up to the ski slopes at Hunter Mountain! Seconds away from the Kaaterskill Flyer lift , main lodge, and bar. Avail for seasonal rental 11/15-4/15 $15000

Aug. 26 – Sep. 2

$192 CAD per night

Guest favourite

Home in Windham

4.99 out of 5 average rating, 318 reviews

Custom-built Catskills retreat, 7 mins from skiing

Located 7 mins from Windham mountain, the house is surrounded by scenic land. Skiing in the winter, foliage in the fall, swimming holes in the summer, sweet air in the spring. Mountain biking, hiking, golf, antiquing, horseback riding, local farms and so much more! The house itself is a true retreat, you will leave totally re-charged. Bird chirping, star gazing, grilling, baking, pancakes, yoga or simply enjoy a few days of not seeing another soul :)

Oct. 13 – 20

$506 CAD per night