Windham, New York

Vacation Rentals in Windham, New York

Discover 89 vacation rental properties in Windham. From 1 to 9 bedrooms. Average $643/night. 100% have pools.

89 verified listings Book securely on VRBO Prices updated March 2026

89 properties available

High Peak Heaven: Cozy Log Cabin on 1 Acre!

High Peak Heaven: Cozy Log Cabin on 1 Acre!

2 beds 1 bath
PoolA/CWiFiBalcony
$135/night
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Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!

Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!

4 beds 4 baths
PoolA/CWiFiBalcony
$470/night
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NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

1 bed 1 bath
PoolA/CWiFiBalcony
$273/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

2 beds 2 baths
PoolA/CWiFiBalcony
$135/night
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Windham ski in-out condo, luxury 2000+ sf modern 5BR, hot tub, pool, boot room++

Windham ski in-out condo, luxury 2000+ sf modern 5BR, hot tub, pool, boot room++

5 beds 4 baths
PoolA/CWiFiBalcony
$1,502/night
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Fantastic 2 family vacation home with EV charger

Fantastic 2 family vacation home with EV charger

3 beds 2 baths
PoolA/CWiFiBalcony
$187/night
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Condo in Windham Mountain Village

Condo in Windham Mountain Village

3 beds 3 baths
PoolA/CWiFiBalcony
$568/night
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Welcome to our home in the mountains, 2 hrs from NYC. 6BR, sleeps 12. Ski in/out

Welcome to our home in the mountains, 2 hrs from NYC. 6BR, sleeps 12. Ski in/out

6 beds 5 baths
PoolA/CWiFiBalcony
$951/night
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Charming 3 bedroom, 2 bathroom chalet on the mountain!

Charming 3 bedroom, 2 bathroom chalet on the mountain!

3 beds 2 baths
PoolA/CWiFiBalcony
$225/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

4 beds 4 baths
PoolA/CWiFiBalcony
$601/night
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Luxury Windham Mtn Slope Side 3 BDRM Condo

Luxury Windham Mtn Slope Side 3 BDRM Condo

3 beds 3 baths
PoolA/CWiFiBalcony
$451/night
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****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!

****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!

4 beds 3 baths
PoolA/CWiFiBalcony
$495/night
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CONVENIENT!Walk 1000ft. to Windham Mtn! Fully furnished 2BR/2Bth Condo w/WiFi

CONVENIENT!Walk 1000ft. to Windham Mtn! Fully furnished 2BR/2Bth Condo w/WiFi

2 beds 2 baths
PoolA/CWiFiBalcony
$371/night
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ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!

ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!

4 beds 3 baths
PoolA/CWiFiBalcony
$1,058/night
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Luxury Ski-in Ski-Out Condo @ Windham Mountain

Luxury Ski-in Ski-Out Condo @ Windham Mountain

3 beds 3 baths
PoolA/CWiFiBalcony
$400/night
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Chalet nestled right in Windham Mountain's quiet beauty-private access to trails

Chalet nestled right in Windham Mountain's quiet beauty-private access to trails

6 beds 5 baths
PoolA/CWiFiBalcony
$640/night
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Ski house just steps from slopes nestled in cute Catskills town of Windham

Ski house just steps from slopes nestled in cute Catskills town of Windham

4 beds 3 baths
PoolA/CWiFiBalcony
$429/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

7 beds 5 baths
PoolA/CWiFiBalcony
$1,800/night
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Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too.

Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too.

3 beds 2 baths
PoolA/CWiFiBalcony
$179/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!

3 beds 3 baths
PoolA/CWiFiBalcony
$1,219/night
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Luxury Home on Windham Mountain! Walk to Slopes

Luxury Home on Windham Mountain! Walk to Slopes

4 beds 4 baths
PoolA/CWiFiBalcony
$767/night
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Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub

Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub

3 beds 2 baths
PoolA/CWiFiBalcony
$367/night
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Luxury Home w/ Deck: Explore the Catskill Mtns!

Luxury Home w/ Deck: Explore the Catskill Mtns!

4 beds 2 baths
PoolA/CWiFiBalcony
$446/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

2 beds 2 baths
PoolA/CWiFiBalcony
$438/night
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Windham Townhouse - Base of Mountain

Windham Townhouse - Base of Mountain

3 beds 3 baths
PoolA/CWiFiBalcony
$424/night
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On the Mountain in Windham, New York in the Catskills

On the Mountain in Windham, New York in the Catskills

4 beds 3 baths
PoolA/CWiFiBalcony
$170/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

4 beds 4 baths
PoolA/CWiFiBalcony
$701/night
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Rare Ski-In/Ski-Out Townhome! Windham Mountain at your back door!

Rare Ski-In/Ski-Out Townhome! Windham Mountain at your back door!

4 beds 4 baths
PoolA/CWiFiBalcony
$902/night
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Cozy townhouse steps away from Windham Mountain- zip code 12496

Cozy townhouse steps away from Windham Mountain- zip code 12496

2 beds 2 baths
PoolA/CWiFiBalcony
$357/night
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Condo on Windham Mountain - Greene County

Condo on Windham Mountain - Greene County

3 beds 3 baths
PoolA/CWiFiBalcony
$630/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

4 beds 4 baths
PoolA/CWiFiBalcony
$612/night
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Ski In Ski Out 2 Bed 2 Bath Condo - Excellent Location

Ski In Ski Out 2 Bed 2 Bath Condo - Excellent Location

2 beds 2 baths
PoolA/CWiFiBalcony
$267/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

7 beds 6 baths
PoolA/CWiFiBalcony
$3,104/night
View Details → Book on VRBO
Comfortable Catskills family home, walking distance to Windham mountain biking

Comfortable Catskills family home, walking distance to Windham mountain biking

3 beds 2 baths
PoolA/CWiFiBalcony
$249/night
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Ski on and Off Windham Mountain Village Townhome Unit

Ski on and Off Windham Mountain Village Townhome Unit

3 beds 3 baths
PoolA/CWiFiBalcony
$225/night
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Windham Mountain Village Condo

Windham Mountain Village Condo

2 beds 2 baths
PoolA/CWiFiBalcony
$224/night
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Luxury Condo w/Views of Windham Mountain

Luxury Condo w/Views of Windham Mountain

2 beds 2 baths
PoolA/CWiFiBalcony
$439/night
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Serenity Summit Luxury Retreat

Serenity Summit Luxury Retreat

5 beds 4 baths
PoolA/CWiFiBalcony
$1,194/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"

4 beds 4 baths
PoolA/CWiFiBalcony
$626/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

5 beds 6 baths
PoolA/CWiFiBalcony
$3,755/night
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Contemporary Renovated Retreat with Mountain Views, Spacious Living Spaces...

Contemporary Renovated Retreat with Mountain Views, Spacious Living Spaces...

5 beds 3 baths
PoolA/CWiFiBalcony
$1,233/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

4 beds 4 baths
PoolA/CWiFiBalcony
$601/night
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New Custom Built Catskill Mountain Chalet with Elevator

New Custom Built Catskill Mountain Chalet with Elevator

6 beds 4 baths
PoolA/CWiFiBalcony
$1,201/night
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WM Village walking distance to Windham Mt Hot Tub Pool 3b, 3Bath SKI

WM Village walking distance to Windham Mt Hot Tub Pool 3b, 3Bath SKI

3 beds 3 baths
PoolA/CWiFiBalcony
$500/night
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Summer at Windham Mountain! On mountain 5 bedroom Retreat!

Summer at Windham Mountain! On mountain 5 bedroom Retreat!

5 beds 3 baths
PoolA/CWiFiBalcony
$992/night
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Windham Moutain Ski House: Walk on & off Slopes - Families Only!

Windham Moutain Ski House: Walk on & off Slopes - Families Only!

4 beds 4 baths
PoolA/CWiFiBalcony
$660/night
View Details → Book on VRBO
2 Bed Ski-In/Out Condo

2 Bed Ski-In/Out Condo

2 beds 2 baths
PoolA/CWiFiBalcony
$658/night
View Details → Book on VRBO
Windham Mountain Village Townhouse

Windham Mountain Village Townhouse

2 beds 2 baths
PoolA/CWiFiBalcony
$1,002/night
View Details → Book on VRBO

Showing 48 of 89 properties

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