Search Windham pet friendly vacation rentals

Our top choices for a great stay

Restored Firehouse One Minute to Skiing on Main St

Restored Firehouse One Minute to Skiing on Main St

Book a stay at this family-friendly vacation home in Windham. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions Windham Mountain Resort ...
10/10 Exceptional! (5 reviews)
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Restored Firehouse One Minute to Skiing on Main St
Cozy Cabin Condo by the Mountain, 5mins to skiing!

Cozy Cabin Condo by the Mountain, 5mins to skiing!

Stay at this vacation home in Windham. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Windham Mountain Resort and Windham Country Club ...
10/10 Exceptional! (5 reviews)
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Cozy Cabin Condo by the Mountain, 5mins to skiing!
Magical Home Located in Windham and Catskills

Magical Home Located in Windham and Catskills

2 out of 5
Stay at this vacation home in Windham. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Windham Mountain Resort and Ashland Park are located ...
10/10 Exceptional! (9 reviews)
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Magical Home Located in Windham and Catskills
5 Bedrooms 5 1/2 Bath Ski Area Views, Walk to Skiing, Huge Common Space & Decks!

5 Bedrooms 5 1/2 Bath Ski Area Views, Walk to Skiing, Huge Common Space & Decks!

Stay at this vacation home in Windham. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Windham Mountain Resort and Windham Country Club ...
9.6/10 Exceptional! (16 reviews)
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5 Bedrooms 5 1/2 Bath Ski Area Views, Walk to Skiing, Huge Common Space & Decks!
In the Heart of Windham - Best Location

In the Heart of Windham - Best Location

Stay at this vacation home in Windham. Enjoy laundry facilities, in-room jetted tubs, and air conditioning. Popular attractions Windham Mountain Resort and Windham ...
9/10 Wonderful! (2 reviews)
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In the Heart of Windham - Best Location
A'Neils Windham Ski Lodge & Family Retreat

A'Neils Windham Ski Lodge & Family Retreat

Book a stay at this ski vacation home in Windham. Enjoy free WiFi, a water park, and a garden. Popular attractions Windham Mountain Resort and Ashland Park are ...
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A'Neils Windham Ski Lodge & Family Retreat
Serendipity Lake House on Lake Heloise. Beautiful private 4000 sq ft lodge

Serendipity Lake House on Lake Heloise. Beautiful private 4000 sq ft lodge

Stay at this vacation home in Windham. Enjoy air conditioning. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
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Serendipity Lake House on Lake Heloise. Beautiful private 4000 sq ft lodge
NEW 5 Bed 5 1/2 Bath Townhouse Walk To Skiing! 900 sq ft Of Mountan View Decks!

NEW 5 Bed 5 1/2 Bath Townhouse Walk To Skiing! 900 sq ft Of Mountan View Decks!

Stay at this vacation home in Windham. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Windham Mountain Resort and Windham ...
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NEW 5 Bed 5 1/2 Bath Townhouse Walk To Skiing! 900 sq ft Of Mountan View Decks!
CLARKS NEST

CLARKS NEST

Stay at this vacation home in Windham. Enjoy free WiFi, laundry facilities, and in-room fireplaces. Popular attractions Windham Mountain Resort and Windham Vineyards ...
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CLARKS NEST
Elegant Catskill Retreat: 8BR Windham Getaway with Hot Tub & Vineyard Views

Elegant Catskill Retreat: 8BR Windham Getaway with Hot Tub & Vineyard Views

Book a stay at this family-friendly vacation home in Windham. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Windham Mountain Resort ...
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Elegant Catskill Retreat: 8BR Windham Getaway with Hot Tub & Vineyard Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.