Maplewood Cottage is situated in Windham, New York State, a 6.4km drive from Windham Mountain and a 27km drive from Hunter Mountain, with an 8-minute walk to Windham's Main Street. This two-bedroom self-catering property sleeps five, boasting a wood-burning fireplace, a mudroom, and a pass-through kitchen window; nearby hiking trails in the Great Northern Catskills offer further outdoor activities.
8.9 9 reviews
Windham
10/25 – 11/01
HK$1921/nighttotal: HK$13447 (7 )
Homey Windham Condo Hike And Ski The Catskill Mtns!
2 2
apartment , Windham
This two-bedroom flat is located in Windham, New York, just 13 kilometres from the Catskill State Park and 16 kilometres from Hunter Mountain, offering easy access to the region's natural beauty and outdoor activities. The property has received very good ratings for cleanliness, user experience and location. The 84 square metre flat comfortably accommodates up to four guests and comes equipped with a kitchen, a balcony, a garden, parking and free Wi-Fi. Guests can enjoy the convenience of a fully equipped kitchen with a dishwasher and microwave oven, as well as relax in the comfortable bedrooms with provided linens.
9.9 106 reviews
Windham
07/24 – 07/26
HK$2774/nighttotal: HK$5548 (2 )
Lothbrok - The "B" Side - 2 Mile Slopes & Town
1 4
house , Windham
This Windham ski house, situated in a peaceful wooded neighbourhood 1.9km from Windham's Main Street and 3.5km from Windham Mountain, offers convenient access to restaurants, pubs, shops, and the movie theatre. The three-bedroom, two-bathroom property sleeps four guests and features a recently renovated interior with a fully equipped kitchen, 50" smart TV, washer/dryer, private deck with Weber BBQ, and shared firepit; ideal for adults seeking a relaxing getaway near Hunter Mountain (a short 15-19 minute drive away).
9.9 40 reviews
Windham
07/24 – 07/26
HK$3335/nighttotal: HK$6670 (2 )
Panoramic Mountain View Townhome With Hot Tub
4 4
apartment , Windham
This apartment is located just outside of downtown Windham, offering stunning views of Windham Mountain and easy access to the town centre, shops, restaurants and attractions. It has received excellent ratings for its location, cleanliness and overall experience. The four-bedroom property can comfortably accommodate up to eight guests and features a spacious living area. Amenities include a fully equipped kitchen with a fridge, freezer, microwave oven and dishwasher, as well as air conditioning, a Jacuzzi, a private deck and a hot tub.
9.9 114 reviews
Windham
07/24 – 07/26
HK$2171/nighttotal: HK$4342 (2 )
Little Bear’s Cottage
Great Location, Cozy & Cute
2 4
house , Windham
This Windham holiday home is conveniently located near the town centre, a short walk from amenities and within 8km of Windham Mountain and 24km of Hunter Mountain. The two-bedroom, one-bathroom property sleeps four guests and boasts a fully equipped kitchen (fridge, microwave), air conditioning, parking, and excellent guest reviews; nearby attractions include restaurants, bars, shops, and a bus stop.
10 83 reviews
Windham
07/24 – 07/26
HK$3346/nighttotal: HK$6692 (2 )
Walk To Town | 2 Mins To Ski | Windham Mill House
1 4
apartment , Windham
This three-bedroom apartment is located in Windham, New York, a short 160km drive from New York City, within walking distance of the local bus stop and bars and restaurants, and a two-minute drive from the Windham Ski Resort. The apartment has been highly rated by previous guests, with excellent scores for location, cleanliness, and overall experience. The apartment has two bathrooms and comfortably sleeps six guests. It comes fully equipped with a kitchen, a Keurig coffee maker, and a smart TV, as well as a private backyard with a fire pit, BBQ grill, and outdoor dining table.
9.0 2 reviews
Windham
07/24 – 07/26
HK$3086/nighttotal: HK$6172 (2 )
Ski, Hike & Golf: Pet-friendly Windham Retreat
3 4
apartment , Windham
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.
9.5 416 reviews
Windham
10/25 – 11/01
HK$1565/nighttotal: HK$10955 (7 )
Studio 3 Beds-slp 3. Downtown Windham. Next To The Ski Resort. Close To Hunter
1 2
studio , Windham
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.
9.8 67 reviews
Windham
08/19 – 08/23
HK$1646/nighttotal: HK$6584 (4 )
Gods Country (3 Bd) Cottage
3 2
apartment , Windham
This Windham Mountain area holiday home, sleeping six guests in three bedrooms and two bathrooms, boasts stunning mountain views and is a short drive from Windham village centre and its amenities. The self-catering property offers a fully equipped kitchen (fridge, microwave, dishwasher), garden, parking, Wi-Fi, and is pet-friendly, ideal for exploring local hiking trails and enjoying nearby skiing and snowboarding at Windham Mountain Resort in winter.
Windham
10/25 – 11/01
HK$1198/nighttotal: HK$8386 (7 )
Romantic Glamping Dome In The Catskill Mountains Near Woodstock, New York
1 2
house , Windham
This unique glamping dome is located in Hensonville, 10.3 kilometres from Catskill State Park and 13 kilometres from Hunter Mountain. This 37 square metre dome offers accommodation for up to four guests, featuring a kitchen with a fridge and microwave, air conditioning, and a garden, with a patio and picnic area for outdoor enjoyment.
9.6 40 reviews
Windham
07/24 – 08/07
HK$4275/nighttotal: HK$59850 (14 )
Waterfront Secluded Log-house W/sauna, Games, More, Mins To Town & Activities
4 2
cabin , Windham
This secluded lodge is located just a short drive from Windham town centre, offering a tranquil escape in a wooded area. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The spacious 195 square metre lodge accommodates up to 10 guests across 3 bedrooms, a loft bed, and a den. Enjoy modern conveniences like a fully equipped kitchen, Wi-Fi, cable TV, and a sauna, as well as outdoor activities like exploring the property, walking along the creek, and relaxing on the wrap-around deck overlooking the pond.
9.9 497 reviews
Windham
07/24 – 07/26
HK$3577/nighttotal: HK$7154 (2 )
Cozycatskillchalet W/ Hot Tub (Catskill Mountains)
1 4
cabin , Windham
This two-bedroom cabin is located in a rural area near Windham, New York, approximately 400 kilometres from New York City and close to the Hunter and Windham Mountains. The property features a six-person hot tub, a Preway chiminea, an outdoor dining table with a fire pit, a five-burner stainless steel BBQ grill, and a full-size foosball table, a dartboard, and a record player for vinyl, CD, cassette, and Bluetooth music playback.
Best family friendly Windham holiday rentals
Among the 155 accommodations in Windham, here are the 4 best family friendly rentals
9.7 167 reviews
Windham
07/24 – 07/26
HK$3421/nighttotal: HK$6842 (2 )
The Windham Cabin W/ Hot Tub
1 4
cabin , Windham
This charming three-bedroom cabin is located just two kilometres from Ski Windham and 40 kilometres from Hunter Mountain, offering easy access to the area's best skiing and snowboarding. The cabin has received excellent ratings for its location, cleanliness, and user experience. The property sleeps six guests comfortably and has a spacious living area, a fully equipped kitchen, and two bathrooms. It also features a private jacuzzi, a working fireplace, a game room with a foosball table and dartboard, and a large deck with stunning views of the surrounding mountains.
10 9 reviews
Windham
07/24 – 08/07
HK$4632/nighttotal: HK$64848 (14 )
Luxury Ski In Ski Out Condo + Amenities
3 2
apartment , Windham
This three-bedroom apartment is located at the base of Windham Mountain, just a short walk from the ski slopes. The property has consistently received excellent reviews for its location, cleanliness, and overall experience. The apartment comfortably sleeps eight guests and offers a modern design with high-end finishes. Guests can enjoy a range of amenities, including a heated outdoor swimming pool, two hot tubs, a fitness centre, and a ski locker room with boot warmers.
The Lodge at Dancing Horse Farm is located in Windham, a rural area near a river, just a few kilometres from Windham Mountain Club and Hunter Mountain Ski and Snowboard Resort. This property has received excellent user ratings, making it a popular choice for travellers. The lodge offers a spacious 427 square metre dwelling with 9 bedrooms, 5 bathrooms, and a capacity for 30 guests. The farm provides a range of amenities for relaxation and entertainment, including a large kitchen, dining room, great room, a 75” 4K HDTV, a pool table, a dart board, a stone patio, a wooden deck with seating, a gas BBQ grill, three fire pit areas, and private walking trails.
10 78 reviews
Windham
10/25 – 11/01
HK$3457/nighttotal: HK$24199 (7 )
Timber Frame Home Only 5 Minutes From Windham Mountain - Perfect For 2 Families!
4 2
apartment , Windham
This charming chalet is located just five minutes from Windham Mountain and a short drive from the town centre, offering a peaceful retreat in a secluded wooded setting. It has consistently received excellent ratings for user experience, location, and cleanliness. The chalet spans 259 square metres and comfortably accommodates eight guests across four bedrooms and three bathrooms. It includes a fully equipped kitchen, a spacious living area with a fireplace, a private garden, a spa, and a terrace, making it ideal for families or groups looking for a relaxing getaway.
Best Windham holiday rentals with a fireplace
9.8 61 reviews
Windham
08/19 – 08/23
HK$6707/nighttotal: HK$26828 (4 )
Condo In Windham Mountain Village
4 2
apartment , Windham
This apartment is located just 0.6 miles from Windham Mountain Resort and 1.5 miles from Windham Country Club, offering a peaceful mountain setting close to all the action. It has consistently received excellent reviews for its location, cleanliness, and overall experience. The property has three bedrooms and three bathrooms, comfortably accommodating up to twelve guests. Amenities include a swimming pool, jacuzzi, terrace, garden, parking, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.
10 4 reviews
Windham
07/24 – 07/26
HK$4016/nighttotal: HK$8032 (2 )
Scenic Catskills Oasis|2 Acres|creek|sunset Views
1 4
apartment , Windham
This renovated 1800s farmhouse, offering 3 bedrooms and 2 bathrooms for up to 7 guests, is situated on 2 private acres just 3 minutes from Windham Mountain and 15 minutes from Hunter Mountain, boasting panoramic Catskill and Batavia Kill creek views. The dog-friendly holiday cottage features a wraparound deck with a barbecue, an indoor fireplace, a sunroom with a 50-inch Smart TV, and a luxurious spa soaking tub, with original 1800s log framing adding historical character.
10 18 reviews
Windham
07/24 – 08/07
HK$1672/nighttotal: HK$23408 (14 )
Cozy Cabin Condo By The Mountain, 5mins To Skiing!
2 2
apartment , Windham
This charming chalet is situated just 3 kilometres from Windham Mountain Resort and 3.2 kilometres from Windham Country Club, offering a tranquil escape in a rural setting. It boasts excellent user ratings, making it a popular choice for travellers. The two-bedroom, two-bathroom property comfortably accommodates up to four guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and Wi-Fi, ensuring a comfortable and enjoyable stay.
10 2 reviews
Windham
07/24 – 07/26
HK$5776/nighttotal: HK$11552 (2 )
3-bedroom All-season Condo At Enclave In Amazing Windham On Mountain
3 4
apartment , Windham
This Windham Mountain Resort ski-in/ski-out condo, situated within the Enclave at Windham, offers convenient access to local attractions such as Hunter Mountain and Zoom Flume. The three-bedroom, three-bathroom apartment sleeps eight guests and includes a washer/dryer, WiFi, and access to a shared pool and fitness centre; jetted bathtubs and family-friendly features add to the appeal.
Frequently asked questions about holiday rentals in Windham
What are some interesting places to visit in or near Windham, NY?
Windham itself is a charming town, but if you want to explore, head to the nearby city of Portland, Maine, which is about an hour's drive. There you can visit the Portland Museum of Art, take a walk along the Eastern Promenade, or enjoy the vibrant Old Port district.
What are the best Airbnb and vacation rentals in Windham?
Which walking or cycling routes are the best in Windham, NY?
For a leisurely stroll, try the scenic Windham Rail Trail, a 4 km paved path perfect for walking, running or cycling. If you're looking for something more challenging, the Sebago Lake Loop Trail offers stunning views of the lake and surrounding mountains.
What sports or outdoor activites can visitors enjoy in and around Windham, NY?
Windham is a great place for outdoor enthusiasts. You can go hiking in the nearby Sebago Lake State Park, try kayaking or canoeing on the lake, or go fishing for trout or bass. In the winter, you can enjoy cross-country skiing or snowshoeing.
What are the best vacation rentals with a pool in Windham?
What other towns or cities can be easily accessed from Windham, NY?
Windham is conveniently located near several other towns and cities. Portland, Maine, is just a short drive away, and you can also easily reach the charming towns of Falmouth, Yarmouth, and Gorham.
What are the best rentals for families and kids in Windham?
What amenities are commonly available in vacation rentals in Windham, NY?
Vacation rentals in Windham typically offer a range of amenities, including fully equipped kitchens, comfortable bedrooms, and often include laundry facilities, Wi-Fi, and outdoor spaces like patios or decks.
What are the best rentals or Airbnbs with a jacuzzi in Windham?
What time of year is best to rent a vacation rental Windham, NY?
The best time to visit Windham really depends on your preferences. If you enjoy warm weather and outdoor activities, summer is ideal. Fall offers beautiful foliage, while winter is perfect for snow sports. Spring is a lovely time to visit, with blooming flowers and milder temperatures.
What are the local dishes in Windham, NY region?
The region is known for its fresh seafood, so try the classic New England clam chowder, lobster rolls, or a fresh catch of the day. For something a little different, try a Maine blueberry pie or a maple-glazed donut.
Destinations nearby
Best Windham holiday rentals with jacuzzi
Windham
08/19 – 08/23
HK$5388/nighttotal: HK$21552 (4 )
Cozy Rustic Bliss Seconds From Windham Mt Resort
5 2
house , Windham
This five-bedroom Windham house, a short distance from Windham Mountain Resort, is conveniently located 17.7km from Hunter Mountain and 14.2km from Catskill State Park. The 279 square metre property boasts a fully equipped kitchen, Jacuzzi, garden, and accommodates up to 11 guests, offering free Wi-Fi, and is ideal for families or groups seeking winter sports access nearby.
This townhouse is located at the top of Windham Mountain Village, just a short walk from the ski lodge and beginner lifts. The property has received excellent ratings for location, cleanliness, and overall experience. The spacious townhouse, with a floor area of 91 square metres, can accommodate up to 8 people. It offers a fully equipped kitchen, a terrace with a gas grill, a fireplace, a community pool, a hot tub, tennis courts, a washer and dryer, and two parking spaces.
9.8 150 reviews
Windham
10/25 – 11/01
HK$3660/nighttotal: HK$25620 (7 )
The Mountain House Windham Retreat With Hot Tub!
4 2
house , Windham
The Mountain House Windham Retreat is located in Windham, just 17 kilometres from Hunter Mountain and 16 kilometres from the Catskill State Park, offering easy access to both winter sports and outdoor activities. The property has received excellent ratings for its location, cleanliness, and overall user experience. This four-bedroom house spans 201 square metres and comfortably accommodates up to eight guests. The property offers a range of amenities including a fully equipped kitchen, a jacuzzi, a terrace, a garden, a spa, a bar, and parking.
10 2 reviews
Windham
07/24 – 07/26
HK$6889/nighttotal: HK$13778 (2 )
Modern 3br/4ba Windham Chalet W/ Hot Tub, Views & Mins To Ski, Bars, Dining!
3 4
chalet , Windham
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.
Best Windham holiday rentals with parking
8.6 4 reviews
Windham
07/24 – 08/07
HK$3709/nighttotal: HK$51926 (14 )
Grand Windham Retreat W/ Fire Pit & Game Room
2 2
cabin , Windham
This Windham lodge is conveniently located within 5km of Windham Vineyards and Winery, Catskill State Park, and less than 10km from Windham Mountain Resort and Ashland Park. This 232 square metre property boasts four bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, terrace, garden, fitness centre, and parking, plus an on-site games room.
10 3 reviews
Windham
07/24 – 07/26
HK$5568/nighttotal: HK$11136 (2 )
Unwind Windham, Chalet
4 4
apartment , Windham
This four-bedroom, three-bathroom flat in Windham is located within the Catskills, offering convenient access to Windham Mountain Resort, Hunter Mountain, Zoom Flume water park, and the Mountain Top Arboretum. Accommodating up to six guests, this property provides internet access and a 11:00 AM check-out, ideal for exploring the area's outdoor activities and natural beauty.
10 3 reviews
Windham
07/24 – 07/26
HK$5438/nighttotal: HK$10876 (2 )
2 Min Walk To Windham Town | Hot Tub | Fire Pit
4 4
apartment , Windham
This four-bedroom, two-bathroom Windham holiday home is situated a short 0.8km walk from Catskill Park, a 3.2km drive from Windham Mountain Ski Resort, and a 4.8km drive from Windham Country Club. Sleeping up to eleven guests, the property offers Wi-Fi, air conditioning, a dryer, and an iron, plus essential toiletries; nearby attractions include Zoom Flume Water Park and Mountain Top Arboretum.
10 12 reviews
Windham
08/19 – 08/23
HK$3737/nighttotal: HK$14948 (4 )
New - Cozy Modern: Stunning Views,3 Mins Ski,bbq,fire Pit,game Room,walk To Town
3 2
apartment , Windham
This spacious Windham, New York holiday home is located 1.3 kilometres from Windham Mountain and within walking distance of Windham's town centre, offering easy access to restaurants, shops, and the Windham Spa. The 179-square-metre, three-bedroom, two-bathroom property sleeps eight guests and features a newly renovated two-level layout, a fully equipped kitchen with a large island, a dedicated games room, and a wraparound deck.