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51 Villa rentals in Windham, NY
Windham, NY
06/19 – 06/24
$909/nighttotal: $4545 (5 )
Secluded Retreat W/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House
1 2
chalet , Windham
This chalet in Windham is conveniently located within 6 miles of Catskill State Park and Windham Mountain Resort. This cottage offers a full kitchen with a refrigerator, microwave, and dishwasher, air conditioning, free WiFi in public areas, an outdoor pool, barbecue grills, and complimentary parking.
Windham, NY
06/19 – 06/24
$1571/nighttotal: $7855 (5 )
Custom Windham Mtn Villa W/ Pool, Theater & Views!
5 2
house , Windham
This 5-bedroom vacation rental is located in Windham, a short drive from Catskill State Park, Hunter Mountain, and the Hudson Athens Lighthouse. The area is known for its natural beauty and outdoor recreation opportunities. The 3,800 square foot home can accommodate up to 16 guests and features a fully equipped kitchen, a fireplace, a balcony, a swimming pool, a garden, and parking. Amenities include air conditioning, free Wi-Fi, and a cable flat-screen TV.
Windham, NY
06/19 – 06/24
$984/nighttotal: $4920 (5 )
Secluded Retreat W/ Pool, Hot Tub, Fire Pit, Views | Windham Mountain House
4 2
chalet , Windham
This 4-bedroom, 3-bathroom mountain lodge in Windham is located just minutes from Windham Mountain Resort and Windham's Main Street, offering convenient access to skiing, dining, and attractions like Briars & Brambles Bookstore. This 2390 sq ft vacation home accommodates up to 8 guests with a spacious open-concept living area, a fully equipped kitchen, a wood-burning stove, a telescope for stargazing, and expansive outdoor living space featuring a pool, hot tub, fire pit, and grill.
9.0 1 review
Windham, NY
06/19 – 06/24
$1165/nighttotal: $5825 (5 )
Lux Windham Getaway - Views & Indoor Heated Pool
5 2
house , Windham
This Windham vacation home is located near Catskill State Park (10 miles) and the Hudson-Athens Lighthouse (30 miles), offering easy access to outdoor recreation and sightseeing. This spacious five-bedroom house boasts 3,300 square feet of living space, an indoor and outdoor heated pool, free Wi-Fi, and parking, accommodating up to 31 guests and providing a relaxing getaway with convenient self-catering amenities.
10 26 reviews
Windham, NY
06/19 – 06/24
$378/nighttotal: $1890 (5 )
Your Windham Mtn. Getaway•hot Spa•bbq•2 Mi To Main
1 2
house , Windham
This Windham Ridge Townhome, located one mile from Windham's Main Street, two miles from the Windham Mountain Club, and a 15-20 minute drive from Hunter Mountain, offers convenient access to area attractions. This two-bedroom, two-and-a-half-bathroom townhome sleeps six, features a fully equipped kitchen, in-unit laundry, a jacuzzi, and a private deck with a hot tub and grill, perfect for après-ski relaxation.
Windham, NY
06/19 – 06/24
$1772/nighttotal: $8860 (5 )
Custom Windham Mtn Villa W/ Pool, Theater & Views!
1 2
house , Windham
This house is located in Windham, just under 2 miles from Windham Mountain Resort and about 2.3 miles from Windham Country Club, offering easy access to popular attractions in the area. The property is ideal for families or groups looking for a comfortable and spacious stay. The home features 4.5 bathrooms, a fully equipped kitchen with a microwave, dishwasher, and stovetop, as well as a private indoor pool, an arcade/game room, a fireplace, and a balcony with barbecue grills. Enjoy a relaxing stay with plenty of entertainment options and amenities for a memorable vacation.
Windham, NY
06/19 – 06/24
$285/nighttotal: $1425 (5 )
2 Mi To Windham Mountain: Scenic Home W/ Fire Pit!
4 2
house , Windham
This Windham vacation home is located 2 miles from Windham Mountain and 8.2 miles from Catskill State Park, with Hunter Mountain a convenient 10 miles away. This 1500-square-foot house features four bedrooms, three bathrooms, sleeps fifteen guests, and includes a fully equipped kitchen, Wi-Fi, a fire pit, and parking.
9.6 40 reviews
Windham, NY
06/20 – 06/27
$545/nighttotal: $3815 (7 )
Waterfront Secluded Log-house W/sauna, Games, More, Mins To Town & Activities
4 2
cabin , Windham
This secluded cabin is located in Windham, just a short drive from the town center and nestled on a 5-acre wooded property near a freshwater creek. It has received excellent ratings for location, cleanliness, and overall user experience. The 2100 square foot cabin comfortably accommodates up to 10 guests in its 3 bedrooms, loft bed, and den. Enjoy modern amenities like a fully equipped kitchen, a sauna, a foosball table, a wood-burning fireplace, a wrap-around deck with pond views, and a game room filled with board games.
10 1 review
Windham, NY
06/19 – 06/24
$327/nighttotal: $1635 (5 )
Vacation Rental Home ~ 2 Mi To Windham Mountain!
1 2
cottage , Windham
This Windham, New York cottage is conveniently located within a 15-minute walk of both the Catskill State Park and Windham Country Club, and a 2-mile drive from Windham Mountain Resort. The pet-friendly cabin offers a fully equipped kitchen with a microwave and dishwasher, 1.5 bathrooms, a cozy fireplace, free Wi-Fi, and parking; nearby activities include hiking, golfing, and skiing.
Windham, NY
06/20 – 06/27
$393/nighttotal: $2751 (7 )
Ski, Hike & More: Year-round Gem In Windham
3 2
house , Windham
This Windham vacation home is conveniently located 11 miles from Hunter Mountain and 9.4 miles from Catskill State Park, offering easy access to outdoor recreation. This 1600-square-foot house features three bedrooms, two bathrooms, sleeps 15 guests, and includes a fully equipped kitchen, free Wi-Fi, on-site parking, and a washer.
10 3 reviews
Windham, NY
06/19 – 06/24
$630/nighttotal: $3150 (5 )
Beautiful Windham Chalet 2 Minutes To Town And The Mountain
4 2
chalet , Windham
This Windham mountain cabin is ideally situated within 3 miles of Catskill State Park and Windham Mountain Resort, offering easy access to hiking, skiing, snowboarding, and mountain biking. The 4-bedroom, 2-bathroom home sleeps 11 guests and boasts a fully equipped kitchen, in-ground swimming pool, and on-site water park, ensuring a comfortable and fun-filled stay.
10 6 reviews
Windham, NY
06/26 – 07/05
$266/nighttotal: $2394 (9 )
Five Ponds Mountain Retreat | 38 Acres • Trails
1 2
house , Windham
This newly built modern guest house is located on a secluded 38-acre property just minutes from Windham Mountain ski resort and Windham town amenities. This 2-bedroom, 1-bathroom guest house accommodates up to 4 guests and features a fully equipped kitchen, air conditioning, internet, garden, and parking, offering panoramic mountain views and five private ponds for a peaceful escape.
Best Windham, NY villas and beach houses with a pool
Among the 51 accommodations in Windham, NY, here are the 3 best villas and beach houses with a pool
Windham, NY
06/19 – 06/24
$955/nighttotal: $4775 (5 )
The Windham Mountain House By Avantstay
1 2
chalet , Windham
This Windham lodge offers serene mountain views in the Catskills region, situated 11 miles from Catskill State Park and 13 miles from Hunter Mountain. This 2390 square foot cabin accommodates up to 12 guests with 1 bedroom and 2 bathrooms, featuring a full kitchen, air conditioning, Wi-Fi, a swimming pool, hot tub, and a private fire pit.
Windham, NY
06/19 – 06/24
$884/nighttotal: $4420 (5 )
222 M² Chalet ∙ 4 Bedrooms ∙ 8 Guests
4 2
chalet , Windham
This house in Windham, located in the Catskill Mountains, is situated just minutes from Windham Mountain Resort and Windham's Main Street, offering convenient access to skiing, summer activities, local dining, and shopping. This spacious 2390 sq ft residence accommodates up to 8 guests across 4 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, a dining table for ten, a swimming pool, hot tub, fire pit, grill, and a wood-burning stove.
Windham, NY
06/26 – 07/05
$692/nighttotal: $6228 (9 )
297 M² Farmhouse ∙ 5 Bedrooms ∙ 14 Guests
5 2
farm , Windham
This Windham resort area vacation rental is located within walking distance of Windham Mountain slopes and offers convenient access to local wineries, eateries, and the natural beauty of the Catskill Mountains, with a bike trail running directly in front. This 3,200 sq ft home accommodates up to 14 guests with 5 bedrooms and features a private hot tub, gas grill, fire pit, and bicycles for guest use, along with a well-equipped kitchen and multiple living areas.
Best Windham, NY houses with a fireplace
9.9 106 reviews
Windham, NY
06/20 – 06/27
$219/nighttotal: $1533 (7 )
Lothbrok - The "B" Side - 2 Mile Slopes & Town
1 2
house , Windham
This 3-bedroom Windham house is located in a quiet neighborhood just one mile from Windham's Main Street, offering easy access to restaurants, pubs, a movie theater, and shops, as well as being 2.2 miles from Windham Mountain. The house features a fully equipped kitchen, a spacious living room with a wood-burning fireplace, a deck with a Weber BBQ, and a dining table, perfect for enjoying meals and relaxing with views of the slopes.
Windham, NY
06/19 – 06/24
$675/nighttotal: $3375 (5 )
Cozy Rustic Bliss Seconds From Windham Mt Resort
5 2
house , Windham
This five-bedroom Windham house, seconds from Windham Mountain Resort, is also conveniently located 11 miles from Hunter Mountain and 8.8 miles from Catskill State Park. This 3000-square-foot home boasts a fully equipped kitchen, Jacuzzi, a garden, and sleeps up to 11 guests, perfect for families or groups enjoying skiing, hiking, or other mountain activities.
10 36 reviews
Windham, NY
06/19 – 06/24
$1178/nighttotal: $5890 (5 )
New Modern Cabin 8 Mins From Skiing-hot Tub & Gym
1 2
cabin , Windham
Three Bears Lodge, a 5-bedroom, 4-bathroom luxury estate in Windham, New York, is located 8 minutes from Windham Mountain and a short drive from local restaurants and attractions. This 4,000-square-foot home boasts a modern spa, chef's kitchen, private zip line, outdoor fire pit, hot tub, expansive deck, and accommodates up to 12 guests, offering a luxurious Windham mountain getaway.
Windham, NY
06/19 – 06/24
$905/nighttotal: $4525 (5 )
New Listing! Bright & Inviting 4 Br Chalet In Windham. 2 Miles To Slopes.
4 2
chalet , Windham
This 4-bedroom, 2-bathroom chalet in Windham offers a rural mountain setting, located a 5-minute drive from Windham Ski Resort and a 10-minute walk to Catskill Park. This family-friendly mountain cabin accommodates up to 12 guests and features a full kitchen, hot tub, garden, and Wi-Fi, providing a convenient base for exploring nearby Hunter Mountain and Zoom Flume Water Park.
Frequently Asked Questions about villa rentals in Windham, NY
What is the best time to visit Windham, NY?
The best time to visit Windham depends on what you're looking for. If you're into skiing and snowboarding, then winter is the best time to visit. If you're looking for warmer weather and hiking, then summer is the best time to visit. Fall is a great time to see the leaves change color, and spring is a great time to enjoy the fresh air and the blooming flowers.
When is it easiest to book a villa rental in Windham, NY?
The easiest time to book a villa rental in Windham is during the off-season, which is typically from April to May and September to October. You'll find the best deals and have the most choices during these months. If you're planning a trip during peak season, it's best to book your villa rental as early as possible.
What are the best villa rentals with a pool in Windham, NY?
There are a lot of great hiking trails in the area, but some of the most popular ones include the Kaaterskill Falls Trail, the Overlook Mountain Trail, and the Devil's Path Trail. These trails offer stunning views of the Catskill Mountains. The Kaaterskill Falls Trail is a relatively easy hike, while the Overlook Mountain Trail and the Devil's Path Trail are more challenging.
What are the best villa rentals with a jacuzzi in Windham, NY?
What are the advantages of renting a house or a villa in Windham, NY
Renting a house or villa in Windham gives you more space and privacy than staying in a hotel. You can cook your own meals, relax in your own living room, and enjoy the outdoors without having to share with other people. It's also a great way to experience the local culture.
What are the best villa rentals for families and kids in Windham, NY?
There are many popular destinations near Windham. You can drive about an hour and a half to Albany, the state capital, which has a lot of museums and historical sites. Or, you can drive about two hours to Saratoga Springs, which is known for its mineral springs and horse racing. If you're looking for something closer, you can visit the town of Hunter, which is about 20 minutes away and has a lot of shops and restaurants.
What are the best pet friendly villa rentals in Windham, NY?
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.
Windham, NY
06/19 – 06/24
$583/nighttotal: $2915 (5 )
Grand Windham Retreat W/ Fire Pit & Game Room
1 2
cottage , Windham
This Windham, New York cottage is conveniently located 1.2 miles from Windham Vineyards and Winery, 2.2 miles from Catskill State Park, and within 6 miles of Windham Mountain Resort. The smoke-free vacation home features a fully equipped kitchen with oven, stovetop, and microwave, a patio, TV, ceiling fan, air conditioning, free Wi-Fi, and on-site amenities including a game room and barbecue grills.
8.6 4 reviews
Windham, NY
06/20 – 06/27
$485/nighttotal: $3395 (7 )
Grand Windham Retreat W/ Fire Pit & Game Room
2 2
cabin , Windham
This Windham vacation home sits within 3 miles of Windham Vineyards and Catskill State Park, and 6 miles from Windham Mountain Resort and Ashland Park, offering easy access to local attractions. The 2,500-square-foot property boasts four bedrooms, two bathrooms, and accommodates six guests, featuring a fully equipped kitchen, fitness center, terrace, and garden, plus on-site BBQ grills and an arcade/game room.
9.9 50 reviews
Windham, NY
06/26 – 07/05
$314/nighttotal: $2826 (9 )
Secluded And Scenic Large Townhouse
1 2
house , Windham
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.
Guest-Favorite Vacation Homes with a Hot Tub in Windham, NY
A soak in your own private hot tub is the ultimate luxury at these slope-side Windham, NY vacation homes.
10 2 reviews
Windham, NY
06/19 – 06/24
$678/nighttotal: $3390 (5 )
Modern 3br/4ba Windham Chalet W/ Hot Tub, Views & Mins To Ski, Bars, Dining!
3 2
chalet , Windham
This Windham chalet is located in Windham, NY, 5 minutes from Windham Mountain Resort and a short drive from Hunter Mountain, offering mountain views and proximity to Zoom Flume and Mountain Top Arboretum. This 3-bedroom, 4-bathroom accommodation sleeps 11 guests and features a 6-person outdoor hot tub, private setting, sophisticated interior, and flexible sleeping arrangements, with internet and air conditioning provided.
10 181 reviews
Windham, NY
06/20 – 06/27
$472/nighttotal: $3304 (7 )
5 Min To Skiing | Hot Tub | Fire Pit | Pool Table
1 2
cabin , Windham
This newly renovated Windham mountain lodge is a 5-minute drive from Windham Mountain ski resort and 2 minutes from Windham town, offering easy access to dining and shopping. Sleeping up to 10 guests, this two-bathroom retreat boasts a private fishing pond, hot tub, pool table, Pac-Man arcade, shuffleboard, fireplace, and firepit, plus panoramic Windham Mountain views from its deck.
Windham, NY
06/26 – 07/05
$303/nighttotal: $2727 (9 )
Mountain Cabin With Scenic Views And Hot Tub
2 2
cabin , Windham
The Mountain Cabin with Scenic Views and Hot Tub is located in Windham, New York, just 9 miles from Hunter Mountain and 29 miles from the Hudson Athens Lighthouse. This 1,800 square foot cabin features two bedrooms, two bathrooms, and a hot tub, comfortably accommodating up to nine guests with amenities like a fully equipped kitchen, a fireplace, and free Wi-Fi.