Compare Vacation Rentals & Airbnb in Windham, NY

Big Hollow, a five-bedroom, two-bathroom duplex near Windham, New York, is located approximately 8km from Windham's shops and restaurants, offering easy access to Hunter, Tannersville, Kaaterskill Falls, North-South Lake, and Colgate Lake.
This spacious property boasts two fully equipped kitchens, a hot tub, a wood-burning fireplace, a pool table, and a large outdoor area with a deck, grill, and fire pit, accommodating large groups or families and providing ample entertainment options.

This apartment is located on a Catskill foothill with views of 5 states, just a short distance from the Windham Mountain Ski Area. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment spans 325 square metres and comfortably accommodates up to 15 guests, with multiple bedrooms and three bathrooms. Enjoy a range of amenities including a fully equipped kitchen, a jacuzzi, a terrace, a garden, and parking, along with internet access and a unique ballroom/event space.

This spacious apartment is situated just 1.6 kilometres from Hunter Mountain Resort and the town centre, making it ideal for exploring the slopes and local amenities. It has received excellent ratings for user experience, location, and cleanliness.
The five-bedroom apartment spans 232 square metres and features a large, modern kitchen, a huge dining room, and two living areas, comfortably accommodating large groups or families. It boasts a range of amenities, including a private lake access, a game room, and a jacuzzi, as well as close proximity to a variety of activities, such as skiing, snowboarding, and golfing.

This Windham lodge is situated on 80 private acres near a ski resort, offering stunning views of a private pond.
Sleeping up to 16 guests, this six-bedroom, 6.5-bathroom property boasts a large kitchen with two ovens and three fridges, a games room with multiple TVs and various games, and high-speed Wi-Fi throughout.

This waterfront property is located just 2km from Dolans Lake and Hunter Mountain, with Pond and the 20th Century Ski Lift within a 15-minute drive. It has received excellent user ratings, making it a popular choice for travellers.
This 6-bedroom, 4-bathroom home spans 223 square metres and offers a range of amenities including a jacuzzi, terrace, garden, tennis court, and parking. Guests can enjoy a fully equipped kitchen, a fireplace, and a games room, as well as a family-friendly environment with a dedicated children's play area.

This secluded ground-level flat in the Northern Catskills offers a private retreat on several acres, located just 2 kilometres from Windham town centre and 3 kilometres from Windham Mountain ski resort.
This apartment provides a newly renovated kitchen, parking, internet, and a spacious yard with a firepit, accommodating up to five guests for outdoor activities.

This 7-bedroom holiday home in the Catskills is conveniently located approximately 14 kilometres from Windham Mountain and 16 kilometres from Hunter Mountain, with Woodstock and Hudson within a 64-kilometre drive.
This expansive 372 square metre property, ideal for up to 16 guests, boasts a chef's kitchen with two dishwashers, a luxurious upstairs living room with a pool table and wet bar, and extensive outdoor living space with a Weber gas grill and firepit.

This family-friendly holiday home is located in the mountains, just 3.7 kilometres from Windham Country Club and within 14.5 kilometres of both Ashland Park and Dolans Lake. The property has received excellent ratings for user experience, location, and cleanliness.
The spacious five-bedroom property, covering 372 square metres, comfortably accommodates up to 15 guests. Enjoy a relaxing stay with features including a fully equipped kitchen, a terrace, a garden, a spa, a tennis court, and a games room.

This spacious Catskills property near Windham and Hunter Mountains offers six bedrooms, four bathrooms, and sleeps sixteen guests, located approximately 2.4km from Zoom Flume water park and 24-32km from the mountains.
The dwelling boasts a private inground pool (seasonal), hot tub, outdoor shower, pool house, playground, speakeasy-style bar with games, fire pit, and ample parking; various bedroom configurations cater to large groups.

This luxurious Windham Mountain chalet, a five-minute drive from Windham Mountain and a 22.5-kilometre scenic drive from Hunter Mountain, offers easy access to several ski resorts.
Sleeping up to eight guests, this four-bedroom, two-bathroom lodge boasts an open-plan layout, a half-wrap-around deck with a stone fire pit, and modern amenities including a dishwasher and down comforters on all beds; nearby activities include hiking and exploring the Catskill Mountains.

The Windham Hilltop Chalet sits on a private 30-acre plot at the top of Windham Mountain, just a few kilometres from the village’s shops and base lodge. It has received excellent ratings for location, cleanliness and user experience.
The chalet can accommodate up to eight guests in its four bedrooms, with a spacious living area and a dedicated games room. Guests can enjoy a fully equipped kitchen, a hot tub, a garden, and a range of activities including hiking, exploring the nearby stream and waterfalls, and enjoying the games room with a pool table, shuffleboard, and foosball.

This Windham mountain lodge offers a private location with spectacular views, situated 5 minutes from Windham Mountain Resort and a short drive from Hunter Mountain.
This 3-bedroom mountain lodge accommodates up to 11 guests, featuring a 6-person outdoor hot tub, air conditioning, internet, and flexible sleeping arrangements, with nearby attractions including Zoom Flume and Mountain Top Arboretum.