Vacation Rentals in Windham Mountain Resort, NY: Compare 10+ Sites & Save

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471 Best Vacation Rentals in Windham Mountain Resort (Starting from $149)

Wintertime
Wintertime
House
Windham, NY, USA
0.8k from Windham Mountain Resort center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Ski resorts

8 Bedrooms22 Guests
New to Booking
$2531
Average price / night
Check Availability
On the Mountain in Windham,  New York in the Catskills
On the Mountain in Windham, New York in the Catskills
House
Windham, NY, 12496, United States
0.5k from Windham Mountain Resort center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.6

Exceptional

5 reviews

$249
Average price / night
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Fireplaces, Home Theater, Ski-In Out Windham Lodge
Fireplaces, Home Theater, Ski-In Out Windham Lodge
House
Windham, NY, USA
0.8k from Windham Mountain Resort center

Fireplace/Heating, Air Conditioner, Internet, Skiing, Pet Friendly, Security/Safety

8 Bedrooms20 Guests
New to Booking
$2362
Average price / night
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Spacious 5BR All-Season Ski-In/Ski-Out Home Modern Renovation & Smart Features
Spacious 5BR All-Season Ski-In/Ski-Out Home Modern Renovation & Smart Features
House
Windham, NY, 12496, United States
0.6k from Windham Mountain Resort center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1067
Average price / night
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Ski, Hike and More Year-Round Gem in Windham
Ski, Hike and More Year-Round Gem in Windham
House
Windham, NY, USA
1.1k from Windham Mountain Resort center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$354
Average price / night
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Luxurious ski in/out,  3-story chalet directly on the slopes of Windham Mountain
Luxurious ski in/out, 3-story chalet directly on the slopes of Windham Mountain
House
Windham, NY, 12496, United States
0.7k from Windham Mountain Resort center

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

7 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$3375
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 Mountain Resort, Windham, New York, USA
1.1k from Windham Mountain Resort 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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Contemporary Renovated Retreat with Mountain Views, Ski-In/Ski-Out,...
Contemporary Renovated Retreat with Mountain Views, Ski-In/Ski-Out,...
House
Windham, NY, 12496, United States
0.7k from Windham Mountain Resort center

Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms12 Guests
New to Booking
$1021
Average price / night
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Cozy Rustic Bliss Seconds from Windham Mt Resort
Cozy Rustic Bliss Seconds from Windham Mt Resort
House
Windham, NY, USA
1.7k from Windham Mountain Resort center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

5 Bedrooms8 Guests
New to Booking
$1062
Average price / night
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Luxury Mountain Log Home, Ski-In/Ski-Out to Windham Resort
Luxury Mountain Log Home, Ski-In/Ski-Out to Windham Resort
House
Windham, NY, 12496, United States
0.8k from Windham Mountain Resort center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms22 Guests
10.0

Exceptional

9 reviews

$4142
Average price / night
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Slope Views Luxe Windham Retreat with Hot Tub!
Slope Views Luxe Windham Retreat with Hot Tub!
House
Windham, NY, USA
1.7k from Windham Mountain Resort center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Hot tubs

5 Bedrooms17 Guests
New to Booking
$647
Average price / night
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Above & beyond.  Perfect house for family, friends & fresh air.
Above & beyond. Perfect house for family, friends & fresh air.
House
Windham, NY, 12496, United States
0.8k from Windham Mountain Resort center

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

3 Bedrooms10 Guests
9.8

Exceptional

38 reviews

$642
Average price / night
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Townhouse W Private Deck & Mt View
Townhouse W Private Deck & Mt View
Apartment
Windham Mountain Resort, Windham, New York, USA
1.9k from Windham Mountain Resort center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering, Ski resorts

4 Bedrooms14 Guests
8.0

Good

8 reviews

$180
Average price / night
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*The View* ski in/out modern luxury at Windham Mountain Resort
*The View* ski in/out modern luxury at Windham Mountain Resort
House
Windham, NY, 12496, United States
0.9k from Windham Mountain Resort center

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

5 Bedrooms14 Guests
9.8

Exceptional

10 reviews

$2511
Average price / night
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The Mountain House Windham Retreat with Hot Tub!
The Mountain House Windham Retreat with Hot Tub!
House
Windham, NY, USA
2.2k from Windham Mountain Resort center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Hot tubs

4 Bedrooms8 Guests
New to Booking
$745
Average price / night
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Luxury Ski-in Ski-Out 4 Bedroom 10 Bed Condo at Whisper Creek Windham Mountain
Luxury Ski-in Ski-Out 4 Bedroom 10 Bed Condo at Whisper Creek Windham Mountain
Apartment
Windham, NY, 12496, United States
1.0k from Windham Mountain Resort center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$710
Average price / night
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Windham Home Near Mountain Biking and Hiking Trails!
Windham Home Near Mountain Biking and Hiking Trails!
House
Windham, NY, USA
2.4k from Windham Mountain Resort center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Ski resorts

2 Bedrooms4 Guests
6.0

Review score

1 reviews

$318
Average price / night
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Red Lift Cabin - Close to town, hiking and biking
Red Lift Cabin - Close to town, hiking and biking
House
Windham, NY, 12496, United States
1.0k from Windham Mountain Resort center

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

3 Bedrooms8 Guests
New to Booking
$1002
Average price / night
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Georgian Garden
Georgian Garden
House
Windham, NY, USA
2.6k from Windham Mountain Resort center

B&bs, Luxury, Cheap, Accommodations, Parking, Guest houses, Homestays, 5-star, Lodgings

6 Bedrooms12 Guests
9.3

Superb

20 reviews

$149
Average price / night
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Fully updated townhome 200 feet from slopes of Windham Mountain
Fully updated townhome 200 feet from slopes of Windham Mountain
House
Windham, NY, 12496, United States
1.0k from Windham Mountain Resort center

Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, TV

3 Bedrooms8 Guests
New to Booking
$1110
Average price / night
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Vacation Rental Home about 2 Mi to Windham Mountain!
Vacation Rental Home about 2 Mi to Windham Mountain!
House
Windham, NY, USA
3.0k from Windham Mountain Resort center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms9 Guests
8.5

Very Good

2 reviews

$552
Average price / night
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Luxury Home on Windham Mountain! Walk to Slopes
Luxury Home on Windham Mountain! Walk to Slopes
House
Windham, NY, 12496, United States
1.0k from Windham Mountain Resort center

Balcony, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Kitchen, Laundry, Living Area

4 Bedrooms11 Guests
9.8

Exceptional

31 reviews

$1303
Average price / night
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3 BDRM/2 Bath in Windham Mountain Village Walking Distance To Mountain with view
3 BDRM/2 Bath in Windham Mountain Village Walking Distance To Mountain with view
House
Windham Mountain Village, NY, 12496, United States
1.0k from Windham Mountain Resort center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Kitchen, Laundry, Living Area

3 Bedrooms9 Guests
9.0

Fabulous

12 reviews

$601
Average price / night
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Summer at Windham Mountain! On mountain 5 bedroom Retreat!
Summer at Windham Mountain! On mountain 5 bedroom Retreat!
House
Windham, NY, 12496, United States
1.0k from Windham Mountain Resort center

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

5 Bedrooms22 Guests
New to Booking
$1099
Average price / night
Check Availability
New Custom Built Catskill Mountain Chalet with Elevator
New Custom Built Catskill Mountain Chalet with Elevator
House
Windham, NY, 12496, United States
1.0k from Windham Mountain Resort center

Dryer, Elevator, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

6 Bedrooms8 Guests
New to Booking
$1334
Average price / night
Check Availability
Ski, Hike & More: Year-Round Gem in Windham
Ski, Hike & More: Year-Round Gem in Windham
House
Windham, NY, 12496, United States
1.1k from Windham Mountain Resort center

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

3 Bedrooms8 Guests
New to Booking
$320
Average price / night
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2 Bedroom Townhouse in front of Windham Mountain Ski Resort
2 Bedroom Townhouse in front of Windham Mountain Ski Resort
House
Windham, NY, 12496, United States
1.1k from Windham Mountain Resort center

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

2 Bedrooms8 Guests
9.8

Exceptional

50 reviews

$178
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 Vacation Rentals in Windham Mountain Resort.

Windham Mountain Resort Vacation Rentals on the Map

Frequently Asked Questions

You can explore 471 verified vacation rentals in Windham Mountain Resort. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Windham Mountain Resort vary depending on the season, property size, and location. Rates typically start from around $149 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Windham Mountain Resort include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Windham Mountain Resort welcome pets. Currently, 32 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Windham Mountain Resort often include amenities such as Fireplace/Heating, Internet, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.