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

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47 Best Vacation Rentals with Pool in Windham (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
1.9k from Windham center

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

5 Bedrooms16 Guests
New to Booking
$1722
Average price / night
Check Availability
Windham Private heated indoor pool.
Windham Private heated indoor pool.
House
Windham, NY, 12496, United States
0.7k from Windham center

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

5 Bedrooms12 Guests
10.0

Exceptional

28 reviews

$1348
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
1.9k from Windham center

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

5 Bedrooms16 Guests
New to Booking
$999
Average price / night
Check Availability
Majestic Villa in Windham - XL Pool, Movie Room, Hot tub, 6 Bedrooms, Gardens
Majestic Villa in Windham - XL Pool, Movie Room, Hot tub, 6 Bedrooms, Gardens
House
Windham, NY, 12496, United States
1.5k from Windham center

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

6 Bedrooms14 Guests
10.0

Exceptional

8 reviews

$791
Average price / night
Check Availability
Luxury Mountain Mansion Huge Pool, Sauna, 7000sqft
Luxury Mountain Mansion Huge Pool, Sauna, 7000sqft
Villa
Windham, NY, USA
5.0k from Windham center

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

8 Bedrooms17 Guests
New to Booking
$1299
Average price / night
Check Availability
Custom Windham Mtn Villa w/ Pool, Theater & Views!
Custom Windham Mtn Villa w/ Pool, Theater & Views!
Villa
Windham, NY, 12496, United States
1.9k from Windham center

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

5 Bedrooms16 Guests
6.0

Review score

2 reviews

$1369
Average price / night
Check Availability
Redwood Retreat in Windham - minutes to Mtn!
Redwood Retreat in Windham - minutes to Mtn!
House
Windham, NY, USA
5.7k from Windham 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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Spacious 5-bedroom house in delightful Windham with Stunning View of Ski Area
Spacious 5-bedroom house in delightful Windham with Stunning View of Ski Area
House
Windham, NY, 12496, United States
2.1k from Windham center

AC, Balcony, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

6 Bedrooms12 Guests
7.8

Good

6 reviews

$877
Average price / night
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All Year-Round Retreat Near Windham Mountain
All Year-Round Retreat Near Windham Mountain
House
NY, USA
7.3k from Windham center

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

5 Bedrooms10 Guests
New to Booking
$706
Average price / night
Check Availability
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
2.8k from Windham 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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Mountain Getaway2BR Btw Hunter&WindhamSkiingHiking
Mountain Getaway2BR Btw Hunter&WindhamSkiingHiking
Apartment
Windham, New York, USA
10.0k from Windham center

Pool, Parking, Internet, Air Conditioner, Child Friendly

2 Bedrooms6 Guests
New to Booking
$299
Average price / night
Check Availability
Ski on and Off Windham Mountain Village Townhome Unit
Ski on and Off Windham Mountain Village Townhome Unit
House
Windham, NY, 12496, United States
2.9k from Windham 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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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
2.9k from Windham 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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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
3.0k from Windham 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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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
3.0k from Windham 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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Condo on Windham Mountain - Greene County
Condo on Windham Mountain - Greene County
Condo
Windham, NY, 12496, United States
3.0k from Windham 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
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
3.1k from Windham 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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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
3.1k from Windham 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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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
3.1k from Windham 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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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
3.2k from Windham 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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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
3.3k from Windham 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
3.3k from Windham 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
3.3k from Windham center

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

3 Bedrooms8 Guests
New to Booking
$1002
Average price / night
Check Availability
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
3.3k from Windham 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
Check Availability
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
3.4k from Windham center

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

4 Bedrooms10 Guests
10.0

Exceptional

24 reviews

$693
Average price / night
Check Availability
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
3.4k from Windham center

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

4 Bedrooms10 Guests
9.6

Exceptional

13 reviews

$693
Average price / night
Check Availability
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
3.4k from Windham 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
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.

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Windham Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 47 verified vacation rentals with a pool in Windham. 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 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 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 welcome pets. Currently, 12 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 often include additional outdoor features such as Pool, Fireplace/Heating, and Balcony/Terrace. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Windham 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.