Ski Chalet Rentals in Windham Vineyards and Winery, NY: Compare 10+ Sites & Save

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33 Best Ski-Chalet Rentals in Windham Vineyards and Winery (Starting from $200)

Beautiful Windham Chalet 2 minutes to the Mountain
Beautiful Windham Chalet 2 minutes to the Mountain
Ski Chalet
Windham, NY, USA
3.7k from Windham Vineyards and Winery center

Cheap, Accommodations, Parking, Cabins, Cottages, Pet-friendly, Lodgings, Places to stay, Family

4 Bedrooms11 Guests
10.0

Exceptional

4 reviews

$361
Average price / night
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Delightful 3-bedroom chalet with WiFi in Windham
Delightful 3-bedroom chalet with WiFi in Windham
Ski Chalet
Windham, NY, 12496, United States
3.4k from Windham Vineyards and Winery center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
10.0

Exceptional

3 reviews

$200
Average price / night
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Fantastic 2 family vacation home with EV charger
Fantastic 2 family vacation home with EV charger
Ski Chalet
Windham Vineyards and Winery, Windham, New York, USA
5.4k from Windham Vineyards and Winery center

Cheap, Accommodations, Parking, Cabins, Cottages, Lodgings, Vacation rentals, Places to stay, Family

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$675
Average price / night
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NEW LISTING! Bright & Inviting 4 BR chalet in Windham. 2 miles to slopes.
NEW LISTING! Bright & Inviting 4 BR chalet in Windham. 2 miles to slopes.
Ski Chalet
Windham, NY, 12496, United States
3.4k from Windham Vineyards and Winery center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms12 Guests
New to Booking
$759
Average price / night
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Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort
Ski Chalet
Windham, NY, USA
5.7k from Windham Vineyards and Winery center

Luxury, Accommodations, Parking, Cabins, Cottages, Pet-friendly, Lodgings, Jacuzzis, Places to stay

5 Bedrooms18 Guests
New to Booking
$951
Average price / night
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Beautiful Windham Chalet 2 minutes to Town and the Mountain
Beautiful Windham Chalet 2 minutes to Town and the Mountain
Ski Chalet
Windham, NY, 12496, United States
3.7k from Windham Vineyards and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms11 Guests
10.0

Exceptional

3 reviews

$443
Average price / night
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Rustic Catskills Cabin with Hot Tub and Mountain Views
Rustic Catskills Cabin with Hot Tub and Mountain Views
Ski Chalet
Prattsville, NY, USA
7.2k from Windham Vineyards and Winery center

Cheap, Accommodations, Parking, Cabins, Cottages, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms8 Guests
9.5

Superb

2 reviews

$230
Average price / night
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Family-Friendly Windham Estate, Swimming Pond, Spa
Family-Friendly Windham Estate, Swimming Pond, Spa
Ski Chalet
Windham, NY, 12496, United States
3.8k from Windham Vineyards and Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Heater, Hot Tub

8 Bedrooms24 Guests
9.8

Exceptional

38 reviews

$2243
Average price / night
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Beautiful Chalet, mins to Hunter/Windham slopes
Beautiful Chalet, mins to Hunter/Windham slopes
Ski Chalet
Jewett, NY, USA
8.3k from Windham Vineyards and Winery center

Cheap, Accommodations, Parking, Cabins, Cottages, Lodgings, Vacation rentals, Places to stay, Family

6 Bedrooms15 Guests
9.5

Superb

10 reviews

$883
Average price / night
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7 Bedroom Luxurious Chalet In Windham, NY
7 Bedroom Luxurious Chalet In Windham, NY
Ski Chalet
Windham, NY, 12496, United States
4.3k from Windham Vineyards and Winery center

Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

7 Bedrooms14 Guests
8.0

Good

1 reviews

$1738
Average price / night
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Woodpecker House - Mountain retreat with hot tub - 10 min to skiing in Hunter & Windham
Woodpecker House - Mountain retreat with hot tub - 10 min to skiing in Hunter & Windham
Ski Chalet
Jewett, NY, USA
9.8k from Windham Vineyards and Winery center

Cheap, Accommodations, Parking, Cabins, Cottages, Lodgings, Vacation rentals, Jacuzzis, Places to stay

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$458
Average price / night
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Ski Chalet In Windham
Ski Chalet In Windham
Ski Chalet
Windham, NY, 12496, United States
4.6k from Windham Vineyards and Winery center

3 Bedrooms7 Guests
New to Booking
$552
Average price / night
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5 Minutes from Windham Mountain
5 Minutes from Windham Mountain
Ski Chalet
Windham, NY, 12496, United States
4.7k from Windham Vineyards and Winery center

Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Toys, TV

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$270
Average price / night
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Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Ski Chalet
Windham, NY, 12496, United States
4.8k from Windham Vineyards and Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms12 Guests
10.0

Exceptional

7 reviews

$1532
Average price / night
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Luxe Lodge w/ Mt View - Hot Tub, Fire Pit, Game Rm, 5 Min to Skiing
Luxe Lodge w/ Mt View - Hot Tub, Fire Pit, Game Rm, 5 Min to Skiing
Ski Chalet
Windham, NY, 12496, United States
4.9k from Windham Vineyards and Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

5 Bedrooms12 Guests
10.0

Exceptional

6 reviews

$916
Average price / night
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NEW Modern Mountain View Chalet in Windham
NEW Modern Mountain View Chalet in Windham
Ski Chalet
Windham, NY, 12496, United States
5.0k from Windham Vineyards and Winery center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$568
Average price / night
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Gorgeous Modern Lodge - Mt View, Hot Tub, Firepit, Game Rm - 5 Min to Skiing
Gorgeous Modern Lodge - Mt View, Hot Tub, Firepit, Game Rm - 5 Min to Skiing
Ski Chalet
Windham, NY, 12496, United States
5.0k from Windham Vineyards and Winery center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms12 Guests
10.0

Exceptional

13 reviews

$903
Average price / night
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Modern 3BR/4BA Windham chalet w/ hot tub, views & mins to ski, bars, dining!
Modern 3BR/4BA Windham chalet w/ hot tub, views & mins to ski, bars, dining!
Ski Chalet
Windham, NY, 12496, United States
5.1k from Windham Vineyards and Winery center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms11 Guests
10.0

Exceptional

2 reviews

$572
Average price / night
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Rustic Mountain view Cabin 5 mins to Ski Area!
Rustic Mountain view Cabin 5 mins to Ski Area!
Ski Chalet
Windham, NY, 12496, United States
5.2k from Windham Vineyards and Winery center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$239
Average price / night
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Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views | Windham Mountain House
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views | Windham Mountain House
Ski Chalet
Windham, NY, 12496, United States
5.5k from Windham Vineyards and Winery center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
New to Booking
$751
Average price / night
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Blue Spruce Chalet — Hot Tub, Pet Friendly
Blue Spruce Chalet — Hot Tub, Pet Friendly
Ski Chalet
Windham, NY, 12496, United States
5.6k from Windham Vineyards and Winery center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
10.0

Exceptional

13 reviews

$540
Average price / night
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Après Chalet|Ski|Luxury|Sauna|HotTub|Firepit|Disco
Après Chalet|Ski|Luxury|Sauna|HotTub|Firepit|Disco
Ski Chalet
Windham, NY, 12496, United States
5.7k from Windham Vineyards and Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms16 Guests
10.0

Exceptional

2 reviews

$890
Average price / night
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Entire lodge in Windham, New York on 12 acres and bordering a state park
Entire lodge in Windham, New York on 12 acres and bordering a state park
Ski Chalet
Windham, NY, 12496, United States
6.2k from Windham Vineyards and Winery center

AC, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave

5 Bedrooms16 Guests
10.0

Exceptional

4 reviews

$1242
Average price / night
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7BR Ski Cabin | HotTub, Sauna | Games | Slope View
7BR Ski Cabin | HotTub, Sauna | Games | Slope View
Ski Chalet
Windham, NY, 12496, United States
7.2k from Windham Vineyards and Winery center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

New to Booking
$749
Average price / night
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Luxurious 3BR/2BA Chalet w/ Panoramic Views Near Windham Mountain on 22+ Acres
Luxurious 3BR/2BA Chalet w/ Panoramic Views Near Windham Mountain on 22+ Acres
Ski Chalet
Gilboa, NY, 12076, United States
7.3k from Windham Vineyards and Winery center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$608
Average price / night
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Luxe Party Retreat: Theater/Karaoke/Games/Hot tub/swimming pool
Luxe Party Retreat: Theater/Karaoke/Games/Hot tub/swimming pool
Ski Chalet
Jewett, NY, 12444, United States
7.8k from Windham Vineyards and Winery center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms16 Guests
10.0

Exceptional

2 reviews

$1378
Average price / night
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Catskills Cozy Hollow - Luxurious secluded A-frame in peaceful forest.
Catskills Cozy Hollow - Luxurious secluded A-frame in peaceful forest.
Ski Chalet
Prattsville, NY, 12468, United States
8.3k from Windham Vineyards and Winery center

Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$403
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Ski-Chalet Rentals in Windham Vineyards and Winery.

Windham Vineyards and Winery Ski-Chalet Rentals on the Map

Frequently Asked Questions

You can explore 33 verified ski chalets in Windham Vineyards and Winery. These include a range of options from catered lodges to self-catered cabins suitable for different group sizes and budgets.

Ski chalet prices in Windham Vineyards and Winery vary depending on the season, location, and level of service. Rates typically start from around $200 per night, with higher prices during peak ski weeks and for premium catered properties.

A catered chalet in Windham Vineyards and Winery usually includes meals prepared by a host, while a self-catered chalet gives you the flexibility to cook your own meals or dine out. The choice depends on whether you prefer convenience or independence during your stay.

Yes, some chalets in Windham Vineyards and Winery offer ski-in/ski-out access, allowing you to reach the slopes directly from the property. Others may be located within a short walk or shuttle ride to the lifts.

Many ski chalets in Windham Vineyards and Winery include wellness amenities such as Fireplace/Heating, Wellness Facilities, and Balcony/Terrace, which are popular for relaxing after a day on the slopes.

In Windham Vineyards and Winery, some chalets can be booked by the room, while others are available for exclusive use. Shared chalets can be a good option for smaller groups, while full chalet rentals offer more privacy for larger parties.

Some chalet providers offer assistance with arranging lift passes and equipment rentals in advance. Checking the property details or contacting the host can help you organize these services before arrival.