Vacation rentals in Windham, NY

This family-friendly vacation home is located in the mountains of Windham, just three miles from Windham Mountain Resort and Windham Country Club, and within six miles of Ashland Park and Ashland Town Hall. The home has received excellent ratings for user experience, location, and cleanliness.
This two-bedroom, two-bathroom vacation rental offers 1,750 square feet of space, comfortably accommodating up to four guests. The property features a swimming pool, jacuzzi, terrace, garden, tennis court, and a fully equipped kitchen with modern appliances.

This Windham vacation rental is conveniently located near Windham Mountain Resort, offering easy access to Hunter Mountain, Zoom Flume, and the Mountain Top Arboretum.
This four-bedroom, two-bathroom apartment sleeps eleven guests and includes in-unit laundry, an on-site fitness center, and all necessary amenities such as hair dryers and an iron/ironing board.

This Windham vacation rental is ideally located near Windham Mountain Ski Resort and Hunter Mountain, offering easy access to both winter and summer activities including Zoom Flume Water Park and the Mountain Top Arboretum.
This 1600-square-foot apartment sleeps eight guests in three bedrooms and two bathrooms, and is pet-friendly, providing ample space for a comfortable stay near kayaking opportunities and the natural beauty of the Windham region.

This Windham townhome is located a 5-minute drive from Windham Mountain and a 1-mile walk to downtown Windham.
This 4-bedroom, 2-bathroom rental accommodates up to 8 guests and features a fireplace, a patio with mountain views, a mudroom, and a sleeping loft.

This Windham vacation home, located 13 miles from Catskill State Park and 15 miles from Hunter Mountain, offers easy access to outdoor recreation.
The 2,500-square-foot house features two bedrooms, two bathrooms, a fully equipped kitchen, a fitness center, a game room, a fire pit, and free Wi-Fi—perfect for families or small groups seeking a comfortable and convenient stay.

This Windham apartment is located in the Meadows, a short distance from the town of Windham, with views of the Windham ski trails. The apartment boasts excellent user, location, and cleanliness ratings, making it a popular choice for travelers.
The two-story home features four bedrooms and two bathrooms, accommodating up to eight guests. The apartment offers a range of amenities, including a fully equipped kitchen, a hot tub, a fire pit, and outdoor decks, providing everything you need for a comfortable and enjoyable stay.

This Windham vacation home, situated on five acres two minutes from town, boasts panoramic views of the Black Dome Mountains and Windham Mountain ski area.
The three-bedroom, two-bathroom house sleeps eight, features a custom timber-frame design with an open floor plan, a fully equipped kitchen, outdoor space with a BBQ and fire pit, and provides various indoor/outdoor games.

This vacation rental is located near Windham, offering stunning views of the surrounding mountains and a nearby horse farm. It's close to a pond and within easy reach of the Idyllic mountain range, making it a perfect spot for nature lovers. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
This spacious home features a large, open floor plan with vaulted ceilings, comfortably accommodating up to 10 guests. The home has a well-equipped kitchen, a grand stone fireplace, multiple bedrooms and bathrooms, a TV loft, and a large deck with a fire pit and fire table.

This cozy two-bedroom house is located in Windham, just minutes from Windham Mountain and Main Street, and a 20-minute drive from Hunter Mountain. The property enjoys excellent ratings for location, cleanliness, and user experience. This home offers a spacious layout with two bedrooms and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, a large yard perfect for outdoor activities, a gas fireplace, a smart TV, and convenient access to local restaurants and shops.

This Windham apartment is located just a minute's drive from Windham Mountain and within walking distance of local restaurants and shops, making it a convenient base for exploring the area. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The rental has two bedrooms, each with a king-size bed and an ensuite bathroom, comfortably accommodating up to seven guests. Enjoy modern amenities like a fully equipped kitchen, a fireplace, a hot tub, and a private patio with a fire pit, offering both indoor and outdoor relaxation and entertainment.

This charming townhome is located just a mile from the town of Windham, NY, and two miles from Windham Mountain, offering easy access to shopping, dining, and skiing. The property has received excellent ratings for location, cleanliness, and user experience.
The spacious townhome features three bedrooms and two bathrooms, comfortably accommodating up to 12 guests. Enjoy amenities like a fully equipped kitchen, two decks with mountain views, a fireplace, and a kids' playroom, perfect for families or groups of friends.

This Windham mountain home is located less than a mile from Catskill State Park and 1.8 miles from the Windham Country Club, offering easy access to hiking, skiing at Windham Mountain Resort (also within 1 mile), and golfing.
This four-bedroom vacation rental sleeps eight guests and features a fully equipped kitchen with a refrigerator, microwave, and dishwasher, a patio, free WiFi, and a fireplace.