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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  New York

  5.  Kingston

  6.  Windham Mountain Resort

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60 Best Vacation Rentals with Pool in Windham Mountain Resort (Starting from $178)

Custom Windham Mtn Villa with Pool, Theater and Views!
Custom Windham Mtn Villa with Pool, Theater and Views!
Villa
Windham, NY, USA
3.4k from Windham Mountain Resort center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

5 Bedrooms16 Guests
New to Booking
$1722
Average price / night
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Luxury Windham Mtn Slope Side 3 BDRM Condo
Luxury Windham Mtn Slope Side 3 BDRM Condo
Condo
Windham, NY, 12496, United States
0.3k from Windham Mountain Resort center

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

3 Bedrooms8 Guests
9.4

Superb

8 reviews

$516
Average price / night
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Lux Windham Getaway - Views & Indoor Heated Pool
Lux Windham Getaway - Views & Indoor Heated Pool
House
Windham, NY, USA
3.4k from Windham Mountain Resort center

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

5 Bedrooms16 Guests
New to Booking
$999
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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Redwood Retreat in Windham - minutes to Mtn!
Redwood Retreat in Windham - minutes to Mtn!
House
Windham, NY, USA
3.8k from Windham Mountain Resort center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms6 Guests
9.3

Superb

16 reviews

$301
Average price / night
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Luxury 4BR/4BA Ski-In / Ski-Out Mountain Stay \"The Four Ski-sons\"
Luxury 4BR/4BA Ski-In / Ski-Out Mountain Stay \"The Four Ski-sons\"
Condo
Windham, NY, 12496, United States
0.8k from Windham Mountain Resort center

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

4 Bedrooms10 Guests
10.0

Exceptional

10 reviews

$766
Average price / night
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Luxury Mountain Mansion Huge Pool, Sauna, 7000sqft
Luxury Mountain Mansion Huge Pool, Sauna, 7000sqft
Villa
Windham, NY, USA
4.8k from Windham Mountain Resort center

Security/Safety, Pool, Oceanfront, Wellness Facilities, Guest Services, Parking, Sports/Activities

8 Bedrooms17 Guests
New to Booking
$1299
Average price / night
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5-Star. Luxury Condo, Heated Pool, Hot Tub, Ski in/out @ Windham
5-Star. Luxury Condo, Heated Pool, Hot Tub, Ski in/out @ Windham
Condo
Windham, NY, 124296, United States
0.9k from Windham Mountain Resort center

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

4 Bedrooms10 Guests
10.0

Exceptional

24 reviews

$693
Average price / night
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Mountain Getaway2BR Btw Hunter&WindhamSkiingHiking
Mountain Getaway2BR Btw Hunter&WindhamSkiingHiking
Apartment
Windham Mountain Resort, Windham, New York, USA
6.3k from Windham Mountain Resort center

Pool, Parking, Internet, Air Conditioner, Child Friendly

2 Bedrooms6 Guests
New to Booking
$299
Average price / night
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5-Star Lux Condo, Heated Pool, Hot Tub, Ski in/out @ Windham
5-Star Lux Condo, Heated Pool, Hot Tub, Ski in/out @ Windham
Condo
Windham, NY, 12496, United States
0.9k from Windham Mountain Resort center

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

4 Bedrooms10 Guests
9.6

Exceptional

13 reviews

$693
Average price / night
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All Season Luxury Condo in Windham/ Ski On - Ski Off
All Season Luxury Condo in Windham/ Ski On - Ski Off
Condo
Windham, NY, 12496, United States
0.9k from Windham Mountain Resort center

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

4 Bedrooms12 Guests
10.0

Exceptional

15 reviews

$802
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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2 Bed Ski-In/Out Condo
2 Bed Ski-In/Out Condo
Condo
Windham, NY, 12496, United States
0.9k from Windham Mountain Resort center

AC, Dryer, Fitness Equipment, Free Parking, Internet, Laundry, No Smoking, Pool, Washer

2 Bedrooms6 Guests
New to Booking
$709
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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Luxury Ski-in Ski-Out Condo + Amenities
Luxury Ski-in Ski-Out Condo + Amenities
Condo
Windham, NY, 12496, United States
1.0k from Windham Mountain Resort center

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

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$630
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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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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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
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Steps away from the magic carpet that brings you right to the lodge!
Steps away from the magic carpet that brings you right to the lodge!
House
Windham, NY, 12496, United States
1.1k from Windham Mountain Resort center

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

3 Bedrooms10 Guests
10.0

Exceptional

12 reviews

$1656
Average price / night
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Cozy Family-Friendly Townhouse Steps from Windham Mountain Resort - Unit 33
Cozy Family-Friendly Townhouse Steps from Windham Mountain Resort - Unit 33
House
Windham, NY, 12496, United States
1.2k from Windham Mountain Resort center

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

2 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$464
Average price / night
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Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
House
Windham, NY, 12496, United States
1.2k from Windham Mountain Resort center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$608
Average price / night
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Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo
Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo
Condo
Windham, NY, 12496, United States
1.2k from Windham Mountain Resort center

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

2 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$459
Average price / night
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Amazing Location, Steps Away from Magic Carpet to Main Lodge.
Amazing Location, Steps Away from Magic Carpet to Main Lodge.
House
Windham, NY, 12496, United States
1.3k from Windham Mountain Resort center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$438
Average price / night
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Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
House
Windham, NY, 12496, United States
1.3k from Windham Mountain Resort center

AC, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$544
Average price / night
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Ski on and Off Windham Mountain Village Townhome Unit
Ski on and Off Windham Mountain Village Townhome Unit
House
Windham, NY, 12496, United States
1.4k from Windham Mountain Resort center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
7.0

Good

6 reviews

$365
Average price / night
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3-bedroom All-Season condo at Enclave in amazing Windham ON MOUNTAIN
3-bedroom All-Season condo at Enclave in amazing Windham ON MOUNTAIN
Condo
Windham, NY, 12496, United States
1.4k from Windham Mountain Resort center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Fitness Equipment

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1490
Average price / night
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Condo on Windham Mountain - Greene County
Condo on Windham Mountain - Greene County
Condo
Windham, NY, 12496, United States
1.5k from Windham Mountain Resort center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Kitchen, Laundry

3 Bedrooms8 Guests
New to Booking
$1772
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 with Pool in Windham Mountain Resort.

Windham Mountain Resort Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 60 verified vacation rentals with a pool in Windham Mountain Resort. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Windham Mountain Resort vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $178 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Windham Mountain Resort offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Windham Mountain Resort welcome pets. Currently, 20 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Windham Mountain Resort often include additional outdoor features such as Pool, Fireplace/Heating, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Windham Mountain Resort offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.