This family-friendly property is situated in the mountains of Windham, just 3.2km from Windham Mountain Resort and Windham Country Club. The house has received excellent ratings for its location, cleanliness, and overall user experience. The property has three bedrooms and two bathrooms, spanning 251 square metres. Guests can enjoy a range of amenities including a Jacuzzi, a terrace, a garden, a tennis court, and a fully equipped kitchen.
10 8 reviews
Windham
07/24 – 07/26
HK$2755/nighttotal: HK$5510 (2 )
The Mad Brook House | Walk To Main St, Windham
1 4
apartment , Windham
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.
9.8 12 reviews
Windham
07/24 – 08/07
HK$2182/nighttotal: HK$30548 (14 )
On The Mountain In Windham, New York In The Catskills
4 2
apartment , Windham
This Windham mountain property is situated less than 1.6km from both the Catskill State Park and Windham Mountain Resort, and 2.9km from the Windham Country Club, offering easy access to hiking, skiing, snowboarding, and mountain biking. Sleeping eight guests in four bedrooms, this holiday home boasts a fully equipped kitchen with fridge, microwave, and dishwasher, a patio, garden, parking, free Wi-Fi, and a fireplace, perfect for family getaways or group trips.
10 54 reviews
Windham
06/26 – 07/05
HK$3283/nighttotal: HK$29547 (9 )
"New Home" Idyllic Mt Views ,Pond & Horse Farm Views 2 Min To Town
3 2
apartment , Windham
This spacious holiday home is located just a short drive from the Windham Mountain Ski Resort, offering stunning views of the surrounding mountains, horse farm, and a grand pond. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers. The property has a large open floor plan with vaulted ceilings, a grand stone fireplace, and a spacious TV loft area, comfortably accommodating up to 10 guests. The home features a fully equipped kitchen, a spacious deck with an outdoor fire pit and fire table, and a peaceful and serene setting, perfect for relaxing and enjoying the beautiful surroundings.
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.
Windham
07/24 – 08/07
HK$2284/nighttotal: HK$31976 (14 )
Mountain Cabin With Scenic Views And Hot Tub
2 2
cabin , Windham
This two-bedroom lodge in Windham is situated 15 km from Catskill State Park, 47 km from the Hudson Athens Lighthouse, and 18 km from Hunter Mountain. The 167 square metre property offers a fully equipped kitchen, a hot tub, and a garden, and can comfortably accommodate up to 9 guests.
This Windham Mountains lodge is conveniently located near Windham Mountain ski resort, within driving distance of Hunter Mountain and attractions such as the Mountain Top Arboretum and Zoom Flume water park. The 23-square-metre self-catering retreat offers one bedroom, one bathroom, sleeps two guests, and includes a kitchenette, fireplace, hot tub, Wi-Fi, Smart TV, and laundry facilities.
Windham
06/26 – 07/05
HK$2900/nighttotal: HK$26100 (9 )
Cozy Windham Getaway
4 2
apartment , Windham
This Windham townhouse is situated a 5-minute drive from Windham Mountain and is 1.6 kilometres from the town centre. This spacious property offers accommodation for eight guests across three bedrooms and a sleeping loft, featuring two bathrooms, a fireplace, a rear patio with mountain views, and a practical mudroom.
This alpine chalet is located in Windham, within a short walk of the town's shops and restaurants, and mere minutes from the Windham ski slopes. Accommodating up to nine guests, this four-bedroom, three-bathroom property offers panoramic ski-slope views, a fully equipped kitchen including a dishwasher and microwave, and a garden, with Wi-Fi and parking provided.
9.9 143 reviews
Windham
07/24 – 07/26
HK$5137/nighttotal: HK$10274 (2 )
Wow! Panoramic Mountain View, Minutes To Windham!
1 4
apartment , Windham
This Windham, New York holiday home sits on a secluded 16-hectare plot, 13 kilometres from the historic town of Windham, offering expansive mountain views. The property boasts three bedrooms sleeping up to six guests, a well-equipped kitchen with dishwasher, a Jacuzzi, and a large deck with fire pit; high-speed internet and a Smart TV are also provided.
10 3 reviews
Windham
07/24 – 08/07
HK$4100/nighttotal: HK$57400 (14 )
Beautiful Windham Chalet 2 Minutes To Town And The Mountain
4 2
chalet , Windham
This Windham mountain lodge is situated within 5km of Catskill State Park and Windham Mountain Resort, offering easy access to hiking trails, skiing, and snowboarding. Sleeping up to 11 guests, this four-bedroom, two-bathroom property boasts a swimming pool, terrace, garden, and all mod cons including a fully equipped kitchen and Wi-Fi; plus, it's pet-friendly.
9.9 114 reviews
Windham
06/26 – 07/05
HK$1150/nighttotal: HK$10350 (9 )
Little Bear’s Cottage
Great Location, Cozy & Cute
2 2
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.
Best family friendly Windham holiday rentals
Among the 155 accommodations in Windham, here are the 4 best family friendly rentals
9.9 78 reviews
Windham
08/19 – 08/23
HK$3436/nighttotal: HK$13744 (4 )
Wake Up To Mountain Magic Year-round (Hot Tub)
1 2
apartment , Windham
This cosy Windham cottage, near Hunter and Windham, New York, is a 7-8 minute drive from both Windham and Hunter Mountain ski resorts. Sleeping six guests, this fully updated two-bedroom, one-bathroom property boasts a wood-burning stove, hot tub with mountain views, and a private fire pit; nearby Colgate and Silver Lake offer hiking, swimming, kayaking, and fishing opportunities.
Windham
07/24 – 07/26
HK$4829/nighttotal: HK$9658 (2 )
Ski Chalet In Windham
3 4
chalet , Windham
This Windham lodge is located 3.2 kilometres from Windham Mountain Resort and less than two hours from New York City, offering a convenient escape. This family-friendly property accommodates seven guests across three bedrooms and two bathrooms, featuring a well-equipped kitchen, a sunken great room with a fireplace, and a finished basement game room with Foosball and karaoke.
9.6 45 reviews
Windham
06/26 – 07/05
HK$1521/nighttotal: HK$13689 (9 )
Mitchell Hollow Home
1 2
apartment , Windham
This cosy house is located just a few minutes' drive from Windham Mountain and the Main Street, with Hunter Mountain 32km away. It has received excellent ratings for location, cleanliness, and user experience. The house is ideal for families, with two bedrooms and a capacity of four guests. It comes equipped with a full kitchen, a spacious living area, and a large dining area, plus a range of amenities including a gas-powered fireplace, a Smart TV, and a selection of games for all ages. The large garden offers a barbecue grill, ample parking, and a great hill for sledding.
10 9 reviews
Windham
07/24 – 07/26
HK$5592/nighttotal: HK$11184 (2 )
Luxury Ski In Ski Out Condo + Amenities
3 4
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.
Best Windham holiday rentals with a fireplace
Windham
07/24 – 07/26
HK$6305/nighttotal: HK$12610 (2 )
Cozy Rustic Bliss Seconds From Windham Mt Resort
5 4
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.
10 4 reviews
Windham
07/24 – 08/07
HK$4498/nighttotal: HK$62972 (14 )
Modern Mountain View Chalet In Windham
4 2
chalet , Windham
This Windham lodge is situated 5 minutes from Windham Mountain Resort and 15 minutes from Hunter Mountain, offering ski access and proximity to Zoom Flume water park. This spacious four-bedroom property accommodates up to 10 guests, featuring a modern open-plan layout, a gourmet kitchen, a furnished deck with a fire pit, and high-speed WiFi for a comfortable stay.
9.8 67 reviews
Windham
07/24 – 07/26
HK$2065/nighttotal: HK$4130 (2 )
Gods Country (3 Bd) Cottage
3 4
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.
9.6 82 reviews
Windham
08/19 – 08/23
HK$1736/nighttotal: HK$6944 (4 )
Catskills Home, 5 Mins To Windham Mtn Resort!
2 2
house , Windham
This charming house is situated just 5 kilometres from Windham Mountain Resort and 14 kilometres from Catskill State Park, making it an ideal base for exploring the beautiful Catskill region. It has consistently received excellent ratings for its location, cleanliness, and user experience. The property offers 102 square metres of living space, comfortably accommodating up to 6 guests in its two bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a relaxing terrace, a garden, a spa, and free Wi-Fi, making this a perfect choice for families or groups seeking a comfortable and convenient stay.
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
9.9 35 reviews
Windham
08/19 – 08/23
HK$3581/nighttotal: HK$14324 (4 )
Cozy Modern: Views, 3 Min Ski, Fire Pit, Game Room
1 2
apartment , Windham
Windy Hollow is a spacious holiday home located just 1.3 kilometres from Windham Mountain Club, a short walk from the centre of Windham, and within easy driving distance of other popular Catskill destinations. The property has excellent user, location and cleanliness ratings. The home is designed to accommodate up to 8 guests and features multiple gathering spaces, a dedicated playroom for children, a fully equipped kitchen and a wood-burning stove. Amenities include a jacuzzi, a garden, parking, internet access and a wraparound deck, perfect for enjoying the views and stargazing.
9.8 69 reviews
Windham
07/24 – 08/07
HK$2102/nighttotal: HK$29428 (14 )
Modern Windham Retreat W/ Hot Tub & Fire Pit
1 2
apartment , Windham
This modern apartment is located just a short walk from Windham town centre and a minute's drive from Windham Mountain, offering easy access to restaurants, shops and attractions. It boasts excellent user, location and cleanliness ratings. The apartment has two bedrooms, each with a king-size bed and an ensuite bathroom, comfortably accommodating up to seven guests. Amenities include a fully equipped kitchen, air conditioning, a jacuzzi, a garden, parking, and access to a stream for fishing and swimming.
9.7 40 reviews
Windham
07/24 – 07/26
HK$3001/nighttotal: HK$6002 (2 )
Cozy Mtn-view Chalet < 2 Mi To Windham Slopes
2 4
cabin , Windham
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.
9.7 136 reviews
Windham
07/24 – 08/07
HK$8488/nighttotal: HK$118832 (14 )
Ski Mountain Chalet W/ Hot Tub, Fireplace, Game Room -Windham Mountain
6 2
apartment , Windham
This six-bedroom property is situated just 2.1 kilometres from Windham Country Club and 4.3 kilometres from Windham Mountain Resort, offering easy access to both attractions. The property has received excellent ratings for location, cleanliness, and user experience. The home spans 353 square metres and features a fully equipped kitchen, four bathrooms, a spa tub, a patio, barbecue grills, and a games room. Guests can enjoy a range of amenities including internet access, air conditioning, and parking.
Best Windham holiday rentals with parking
9.0 12 reviews
Windham
07/24 – 07/26
HK$6767/nighttotal: HK$13534 (2 )
3 Bdrm/2 Bath In Windham Mountain Village Walking Distance To Mountain With View
3 4
apartment , Windham
This Windham mountain property is situated 2.4km from Windham Country Club, a 15-minute walk from both the Catskill State Park and Windham Mountain Resort. This four-bedroom, two-bathroom holiday home sleeps nine guests and boasts an indoor pool, hot tub, tennis court, BBQ grills, fully equipped kitchen, and fireplace; enjoy nearby hiking, skiing, and other outdoor activities.
9.6 29 reviews
Windham
06/26 – 07/05
HK$1759/nighttotal: HK$15831 (9 )
Vacation Rental Home ~ 2 Mi To Windham Mountain!
3 2
apartment , Windham
This spacious Windham holiday home is situated near Windham Mountain and approximately 16km from Hunter Mountain, offering convenient access to both ski resorts. Sleeping up to nine guests, this three-bedroom, one-and-a-half-bathroom property boasts a fully equipped kitchen, sunroom with mountain views, fireplace, and pet-friendly accommodation (additional charge applies); July 4th fireworks are visible from the property.
9.6 8 reviews
Windham
07/24 – 07/26
HK$6479/nighttotal: HK$12958 (2 )
Great For Families & Groups!
4 4
apartment , Windham
This family-friendly house is located in the mountains of Windham, just 3.2 kilometres from Windham Mountain Resort and Windham Country Club, and within a 19.3 kilometre radius of Zoom Flume and Mountain Top Arboretum. The property has received excellent user ratings, reflecting its comfortable and enjoyable atmosphere. This spacious house can accommodate up to 12 guests and features four bedrooms and two bathrooms. It offers a fully equipped kitchen, a relaxing garden with a terrace, and free WiFi, ensuring a comfortable and enjoyable stay for all.
9.8 27 reviews
Windham
07/24 – 07/26
HK$7105/nighttotal: HK$14210 (2 )
Beautifully Restored 6br In The Heart Of Windham
6 4
apartment , Windham
This six-bedroom apartment is situated in Windham, less than 1.6 kilometres from Windham Mountain and within walking distance of Main Street's restaurants, coffee shops, and wine bars. The property offers spacious accommodation for up to 13 guests, with a fully equipped kitchen, a large family room, and a garden.