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Windham Vacation Rentals

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Our Favorite Vacation Rentals in Windham

  • ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***
    ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***
    Excellent2br Home/Apartment
    HolidayLettingsFrom $289
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  • The Presidential Suite at Brie & Bordeaux
    The Presidential Suite at Brie & Bordeaux
    Excellent3br Home/Apartment
    HolidayLettingsFrom $487
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  • Amazing 4 BR on Windham
    Amazing 4 BR on Windham
    Excellent4br Country House
    HolidayLettingsFrom $658
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  • Windham Mountain Ski House with Great Views
    Windham Mountain Ski House with Great Views
     3br Home/Apartment
    HolidayLettingsFrom $530
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  • Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.
    Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.
     4br Chalet
    HolidayLettingsFrom $779
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  • NEW! Windham Condo w/ Pool & Balcony Near Hiking!
    NEW! Windham Condo w/ Pool & Balcony Near Hiking!
     1br Home/Apartment
    HolidayLettingsFrom $251
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  • Modern Home w/ Deck, 5 Minutes to Windham Resort!
    Modern Home w/ Deck, 5 Minutes to Windham Resort!
     3br Home/Apartment
    HolidayLettingsFrom $316
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  • *4SeasonNirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw
    *4SeasonNirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw
    Excellent4br Home/Apartment
    HolidayLettingsFrom $358
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See all 400 deals in Windham

Windham Vacation Rentals with a Pool

  • Your home for outdoor fun!
    Your home for outdoor fun!
    Excellent2br Home/Apartment
    AirbnbFrom $238
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  • Mountain View Retreat ✦ Picturesque & Peaceful
    Mountain View Retreat ✦ Picturesque & Peaceful
    Excellent2br Home/Apartment
    AirbnbFrom $232
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See all deals in Windham with a pool

Windham Vacation Rentals with Wi-Fi

  • Brand New Windham Ski/Summer House
    Brand New Windham Ski/Summer House
    Excellent4br Home/Apartment
    AirbnbFrom $670
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  • Ideal mountainview suite, 5 minutes to ski area!
    Ideal mountainview suite, 5 minutes to ski area!
    ExcellentBedroom
    AirbnbFrom $87
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  • The Windham Loft
    The Windham Loft
    Excellent2br Home/Apartment
    AirbnbFrom $285
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  • Mountainside Ski Deluxe Windham Apt - 1Br 1Bath
    Mountainside Ski Deluxe Windham Apt - 1Br 1Bath
    Excellent1br Home/Apartment
    AirbnbFrom $242
    View Deal
See all deals in Windham with WiFis

Windham Pet-Friendly Vacation Rentals

  • Mountain House Retreat
    Mountain House Retreat
    Excellent5br Home/Apartment
    HolidayLettingsFrom $547
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  • Family Fun Catskill Mountain Retreat
    Family Fun Catskill Mountain Retreat
    Nice4br Home/Apartment
    HolidayLettingsFrom $630
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  • Historic Catskill Mountain House close to Windham
    Historic Catskill Mountain House close to Windham
     7br Home/Apartment
    HolidayLettingsFrom $887
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  • Hunter Mt-REDUCED~Amazing Views-Big House! 5 min to SLOPES!
    Hunter Mt-REDUCED~Amazing Views-Big House! 5 min to SLOPES!
    Good5br Home/Apartment
    HolidayLettingsFrom $676
    View Deal
See all deals in Windham that allow pets

Windham New York Travel Guide

In New York's Catskill Mountain region, Windham is the perfect spot to venture to escape the busy city vibes of the Big Apple for a day or two, and enjoy getting back to basics among nature.

Things to Do in Windham New York

Windham is known as the home of the Windham Mountain Resort -- a popular vacation spot for avid skiers and snowboarders. The less nimble can opt to hang out at the snow-themed amusement park where kids and families can try their hand at ice skating and tubing. In the fall and spring months, visitors can sample the fresh produce and concoctions conjured up by the Windham wineries and vineyards.

Best Time to Visit Windham New York

Windham is a year-round travel destination. Those hoping to visit the Windham mountain resort are best to visit Windham in the winter months (December to February) when conditions are optimum for snow sports. Those hoping to go wine tasting or walking will enjoy the crisp, fresh temperatures of spring and fall.

Price and Availability in Windham

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The most expensive month to stay in a vacation rental in Windham is in January, while the cheapest month is in April. The most popular time to book a vacation rental in Windham is in the high season in February. Windham has its low season in April, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Windham tends to be Monday, while the most expensive day tends to be Friday. Vacation homes in Windham tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Windham

97º 51º
4.72
96º 57º
4.2
94º 43º
5.62
83º 27º
3.77
64º 4º
5.59
62º 13º
3.04
63º -10º
2.39
73º 2º
3.08
56º 7º
3.06
70º 19º
4.17
90º 41º
1.64
97º 48º
3
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Rainy days
This climate histogram shows you the weather patterns in Windham. The hottest month in Windham is June, when temperatures peak at 97 ˚F. The coolest month is January, when temperatures drop to -10 ˚F. The wettest month in Windham is September with 5.62 inches of rain, while the driest month is May with 1.64 inches of rain.

What Expert Travelers Think

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