Find short term rentals in Windham, NY at the best prices

This 1854 Victorian Inn is located in the Windham business district, offering immediate walking access to restaurants, shops, a deli, a farmers market, entertainment venues, and a bus stop for direct travel to New York City.
This self-catering accommodation offers private bedrooms with en-suite bathrooms for up to two guests, with shared access to a porch, patio, garden, game room, mini golf, and a triplex cinema, and is a short drive from skiing, hiking, and mountain biking trails.

This Windham holiday home is located minutes from Windham Mountain and within walking distance of Windham Park, offering easy access to restaurants, state parks, and hiking trails.
Sleeping up to five guests, this two-bedroom, two-bathroom property boasts a fully equipped kitchen, a wood-burning fireplace, a private deck with mountain views, and access to community amenities including a swimming pool, tennis courts, and a firepit, plus an electric vehicle charger.

This three-bedroom Windham holiday home, 15 minutes (24km) from Ski Windham, 25 minutes (40km) from Hunter Mountain, and 10 minutes (16km) from Zoom Flume, offers stunning Catskill and Helderberg mountain views.
The property boasts a spacious layout sleeping six guests, complete with a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, garden, parking, and excellent guest reviews; internet access is also provided.

This Windham Mountain retreat, situated 3.2km from the Windham Mountain Club, offers a peaceful Catskill Mountains escape near Hunter Mountain.
Sleeping up to six guests, this three-bedroom, two-bathroom property boasts a full kitchen, gas grill, fireplace, Wi-Fi, and ample outdoor deck space; pets are welcome (fee applies).

This two-bedroom apartment is located in Windham, New York, just 1.6 kilometres from Windham Mountain Resort and a short walk from the Wylder event venue, offering a convenient base for exploring the area. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is spacious and can accommodate up to five guests. It comes equipped with a modern kitchen, air conditioning, a garden, and private parking, making it ideal for a comfortable and enjoyable stay. Guests can also enjoy access to high-speed internet, satellite TV, and a range of outdoor activities nearby.

This Windham flat offers excellent walkability to Main Street's shops and restaurants, and is conveniently located 1 kilometre from Windham Mountain Ski Resort.
This 115 square metre condo accommodates up to four guests, featuring two bedrooms, two bathrooms, air conditioning, free WiFi, and an in-unit washer and dryer.

This Windham cabin, sleeping eight guests in two bedrooms and one bathroom, offers a peaceful retreat with excellent user ratings for cleanliness, location, and overall experience.
The self-catering lodge boasts internet access, air conditioning, parking, and pet-friendly accommodation, promising a comfortable stay with a fully equipped kitchen.

This Catskills lodge is conveniently located near Windham and Hunter Mountain ski resorts, offering easy access to hiking trails such as Kaaterskill Falls.
The single-storey property sleeps six guests across two bedrooms and one bathroom, boasting a fully equipped kitchen, private hot tub with mountain views, gas fireplace, wood-burning fire pit, and outdoor deck with gas grill; parking is available for three vehicles.

This four-bedroom townhouse is located just under 8 kilometres from Windham Mountain Ski Resort and Windham's Main Street, offering easy access to both outdoor activities and town amenities. The property has received very good user ratings, indicating a positive experience for previous guests.
This spacious home spans 130 square metres and comfortably accommodates up to eight guests. The property features a well-equipped kitchen, a private patio with outdoor dining, a wood fireplace, a piano, free Wi-Fi, a washer and dryer, and pet-friendly facilities.

This apartment is located just a short drive from Windham Mountain, offering easy access to skiing and hiking trails, as well as scenic attractions like the Five State Lookout and the Kaaterskill Falls Trail Head. It has consistently received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment is well-equipped with a fully fitted kitchen, providing everything you need for self-catering, and comfortably accommodates up to 6 guests. Guests can enjoy a relaxing stay with amenities like air conditioning, a garden, and parking, making it ideal for families or groups looking for a comfortable and convenient base to explore the region.

This Windham apartment, situated 4.3km from Windham Mountain Resort near Route 23 in the Catskill Mountains, offers easy access to skiing and hiking.
Sleeping five guests across two bedrooms and two bathrooms, the property boasts a well-equipped kitchen, swimming pool, garden, parking, and dedicated Wi-Fi, alongside on-site tennis courts and a fire pit.

This Windham chalet, located within 6.4 kilometres of Windham's premier skiing and hiking trails, offers easy access to outdoor activities.
The spacious three-bedroom property sleeps eight, boasting an open-plan kitchen, living, and dining area, a dedicated games room with a 75-inch TV, and multiple outdoor decks, a fire pit, and BBQ facilities.

This two-bedroom apartment is situated just a short distance from both Windham Mountain Resort and Hunter Mountain, making it ideal for those seeking a ski-centric getaway. It has received excellent ratings from previous guests.
The property comfortably accommodates up to eight guests and features a fully equipped kitchen, a swimming pool, a garden, and parking. You can enjoy stunning mountain views, explore nearby natural attractions like Kaaterskill Falls, and take advantage of the proximity to other activities like Mountain Top Arboretum and Zoom Flume.

This Windham mountain condo is conveniently located 3.4km from Windham Mountain Resort, a 15-minute walk from Catskill State Park and Windham Country Club.
The 111 square metre apartment sleeps eight guests, boasting three bedrooms, two bathrooms, in-unit laundry, free Wi-Fi, and designated parking.

This Windham mountain apartment is situated near Catskill State Park (a 15-minute walk), Windham Country Club (a 15-minute walk), and Windham Mountain Resort (3.4km).
The 74 square metre property sleeps three, boasting two bedrooms, one bathroom, in-unit laundry, free Wi-Fi, a sofa bed, and on-site parking; nearby activities include skiing at Windham Mountain and exploring Catskill State Park.

This Windham apartment, ideally situated between Hunter Mountain (19km) and Windham Mountain (11km), offers easy access to skiing and local amenities.
The two-bedroom, one-and-a-half-bathroom property sleeps five, features a fully equipped kitchen, multiple air conditioning units, a garden, parking, and board games, ensuring a comfortable self-catering stay.

This Hensonville flat offers a convenient base, situated less than 1 kilometre from Black Dome Valley and a short drive to both Hunter Mountain Resort and Windham Mountain Resort.
This 65 square metre apartment sleeps up to four guests, featuring two bedrooms, one bathroom, a well-equipped kitchen with a dishwasher, a wood-burning fireplace, and a private patio with mountain views, with pets welcome for an additional fee.

This 3-bedroom lodge in Jewett is a 6-person accommodation located a short drive from Windham Mountain Resort and Hunter Mountain, offering a convenient base for exploring the Catskills.
This self-catering property includes a fully equipped kitchen with a microwave and dishwasher, three bedrooms with one queen and two double beds, two bathrooms with tub/shower combinations, central heating, a wood-burning stove, and Wi-Fi, with a check-out time of 11:00 AM.

This renovated 1940s Catskills cottage is located by a brook, a short walk from Main Street in Windham, offering peaceful water sounds and convenient access to local shops and cafés.
This two-bedroom flat accommodates up to four guests and features a fully equipped kitchen, air conditioning, Wi-Fi, on-site parking with an EV charger, and a propane fireplace, with a brand-new washer and dryer available for guest use.

This newly renovated 2-bedroom townhouse is situated in the Catskills, offering easy access to Windham Mountain, just 5 minutes away, and Hunter Mountain, 15 minutes away.
This accommodation features heated floors, a pellet stove, complimentary Wi-Fi, a full kitchen with a coffee bar, and Smart TVs, comfortably accommodating up to 6 guests for a ski and work getaway.

This three-bedroom apartment is located just 5 kilometres from Windham Mountain, offering easy access to the slopes and a range of local amenities. Guests have consistently rated the apartment excellent for its location, cleanliness, and overall experience.
The apartment is spacious and modern, comfortably accommodating up to six guests. It features a well-equipped kitchen, a luxurious master bedroom with a Jacuzzi tub, and high-speed internet, ensuring a comfortable and enjoyable stay.

This Windham apartment is situated a 15-minute walk from both Catskill State Park and Windham Country Club, and 3.5km from Windham Mountain Resort, offering easy access to hiking, golfing, and skiing.
The self-catering flat features a fully equipped kitchen with oven, hob, microwave, and dishwasher, a private balcony, and free Wi-Fi in communal areas; it's perfect for exploring the Catskill region.

This property is located in Windham, within a mile of Windham Mountain Resort and Windham Country Club and within six miles of Ashland Park and Ashland Town Hall. It is situated in a peaceful setting, close to attractions but offering a relaxing escape from the hustle and bustle. The house has received excellent user ratings for location, cleanliness, and overall experience.
This holiday home offers two bedrooms and a sofa bed, comfortably accommodating families or groups of friends. It comes equipped with free Wi-Fi, a fully equipped kitchen, parking, and a terrace or balcony, allowing guests to enjoy the beautiful surroundings.

This Catskills Mountains holiday home, located 3.2km from Windham town centre, offers easy access to shops, restaurants, and attractions such as Hunter Mountain (19km), Kaaterskill Falls (29km), and Zoom Flume (13km).
The 203 square metre property boasts four bedrooms, two bathrooms, sleeps six guests, and includes a full kitchen, two decks, a fireplace, free Wi-Fi, a washer/dryer, and ample parking.

This two-bedroom apartment is located in Windham, New York, just 5 kilometres from Windham Mountain and 16 kilometres from Hunter Mountain. It has received very good user ratings, an excellent location rating, and a very good cleanliness rating.
The apartment is 102 square metres in size and can accommodate up to six guests. It has a fully equipped kitchen, a private yard, free Wi-Fi, and air conditioning, making it ideal for families or groups of friends who want to enjoy the beautiful scenery and activities that Windham has to offer.

This newly constructed townhome, offering 2 bedrooms and 2 bathrooms, is located in the Catskills, a mere few minutes from Windham Mountain ski resort and 15 kilometres from Hunter Mountain, with dining and entertainment options nearby.
This family-friendly accommodation provides a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a garden, parking, and free internet, making it ideal for up to 8 guests seeking a comfortable mountain getaway.

This Windham cottage is ideally situated within 5km of Catskill State Park, Windham Mountain Resort, and Windham Country Club, offering easy access to outdoor activities and local amenities.
The pet-friendly property boasts a fully equipped kitchen with a dishwasher, two bathrooms, air conditioning, free Wi-Fi in public areas, and barbecue grills, perfect for families or groups seeking a comfortable self-catering holiday home.

This Windham mountainside property is situated within 9.6km of Windham Vineyards, Windham Mountain Resort, and Windham Country Club, and within 14.5km of Zoom Flume and Tenmile Creek.
This four-bedroom, two-bathroom holiday home sleeps ten guests and boasts a fully equipped kitchen, private patio, fireplace, free Wi-Fi, and access to a spa; nearby activities include skiing at Windham Mountain Resort and waterpark fun at Zoom Flume.