Family-friendly vacation rentals in Windham

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.

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 :)

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.

Cozy Cottage with Stunning Mountain Views

Welcome to Solheim Cottage! Featuring gorgeous mountain views, less than two and a half hours from NYC, and ten minutes from Belleayre Ski Center, this cozy and private cottage is perfect for a romantic couples retreat, two couples, a small family, or a group of friends looking for a relaxing and quiet escape in the historic Catskills. The cottage is a short drive to Phoenicia, Woodstock, Andes, and Margaretville for shopping, dining, antiquing, skiing and exploring.

Redwood Retreat in Windham - Pool! Tennis!

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.

Cozy mountain hideaway - Catskills Windham

Escape to a private Catskill Mountain cabin surrounded by woods and comfort. Video available at vimeo: vimeo/1090353214 Enjoy Wi-Fi, a cozy fireplace, full kitchen, plush Queen bed in the master, plus a loft with another Queen and futon. Bluetooth speakers, Smart TV, A/C & heat, BBQ grill, and outdoor fire pit. Firewood available. Just 25 mins to Windham Mountain. Pet-friendly. Perfect for a peaceful, modern mountain retreat!.

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 that provide restful sleep , sparkling and airy bathrooms and cozy , relaxing living room.

2BDR- Cozy Windham/Hunter Escape

The Windham Escape is a cozy 2 bedroom apartment nestled in the northern Catskill Mountains. It is close to restaurants and dining, great views, family-friendly activities, Hiking, Skiing, Golf and other outdoor activities. Our place is great for friends traveling together, couples, and families (with kids).

Small house, Windham, NY

Our rental house is located in the center of Windham, NY in a walking distance to restaurants, pubs, stores, and only 5 min from the Windham Mountain. It is fully furnished. Inside the house: two bedrooms, living room, kitchen and bathroom with a washing machine and dryer.