We use cookies to provide you with the best browsing experience. The data collected by cookies is used to optimise the website for our users and deliver an appropriate service and relevant information to you. By using our site we assume you’re aware and agree to use the cookies for this purpose.

OKLearn more
Destination Photo

Windham Vacation Rentals

Search

Our Favorite Vacation Rentals in Windham

  • PENTHOUSE w/ SunRoom, deck, Mt view
    PENTHOUSE w/ SunRoom, deck, Mt view
     
    Booking.comFrom $150
    View Deal
  • ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***
    ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***
    Excellent
    HolidayLettingsFrom $289
    View Deal
  • Hunter near Ski Slopes, Catskills Amazing Views!
    Hunter near Ski Slopes, Catskills Amazing Views!
     
    Booking.comFrom $396
    View Deal
  • 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.
     
    HolidayLettingsFrom810 $779
    View Deal
  • Lakefront Cabin
    Lakefront Cabin
     
    Booking.comFrom $1700
    View Deal
  • Beautiful apartment with great views!
    Beautiful apartment with great views!
    Excellent
    HolidayLettingsFrom $231
    View Deal
  • Apple Hill
    Apple Hill
     
    Booking.comFrom $800
    View Deal
  • Ukroatian Mountain Kucha 4 beds, 2 baths, Sleeps 12
    Ukroatian Mountain Kucha 4 beds, 2 baths, Sleeps 12
     
    HolidayLettingsFrom $384
    View Deal
See all 404 vacation rentals in Windham

Windham Vacation Rentals with a Pool

  • Cozy Condo- Windham, NY
    Cozy Condo- Windham, NY
    Excellent
    AirbnbFrom $125
    View Deal
  • ⭐Mountain View Retreat⭐
    ⭐Mountain View Retreat⭐
    Excellent
    AirbnbFrom $213
    View Deal
See all vacation rentals in Windham with a pool

Windham Vacation Rentals with Wi-Fi

  • Brand New Windham Ski/Summer House
    Brand New Windham Ski/Summer House
    Excellent
    AirbnbFrom $934
    View Deal
  • Luxury Log Home with Ski Windham Views
    Luxury Log Home with Ski Windham Views
    Excellent
    AirbnbFrom $1166
    View Deal
  • The Windham Loft
    The Windham Loft
    Excellent
    AirbnbFrom $283
    View Deal
  • Great Windham Contemporary Getaway House !!!
    Great Windham Contemporary Getaway House !!!
    Excellent
    AirbnbFrom $582
    View Deal
See all vacation rentals in Windham with WiFis

Windham Pet-Friendly Vacation Rentals

  • Mountain House Retreat:Let It Snow! Book Now! Over 1 Foot Of Fresh Powdered Snow
    Mountain House Retreat:Let It Snow! Book Now! Over 1 Foot Of Fresh Powdered Snow
    Excellent
    HolidayLettingsFrom $532
    View Deal
  • Family Fun Catskill Mountain Retreat
    Family Fun Catskill Mountain Retreat
    Nice
    HolidayLettingsFrom $630
    View Deal
  • SIX BEDROOMS SIX BATHS
    SIX BEDROOMS SIX BATHS
     
    FlipkeyFrom $716
    View Deal
  • Lakefront Windham Area Home w/ Boat & Dock!
    Lakefront Windham Area Home w/ Boat & Dock!
     
    HolidayLettingsFrom $496
    View Deal
See all vacation rentals 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

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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

90º 41º
1.64
97º 48º
3
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
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
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

Vacation Rentals in Windham

Find the perfect vacation rental for your trip at AllTheRooms.com. We compare Airbnb, Homeaway, VRBO and many more. AllTheRooms has 404 vacation rentals, hotels and other great places to stay while you enjoy Windham, with everything from budget hostels and homestays to luxury Airbnbs and hotels. For those wanting to keep costs down, the cheapest place to stay in Windham is only $50 a night. An average accommodation in Windham costs on average $361 a night.

If you need to stay connected during your vacation, then you can choose from over 221 accommodations in Windham that have WiFi. 11 of our accommodations come with breakfast in the price. Fitness fanatics can get a workout in during their stay by choosing from 8 accommodations that have gyms. Driving to Windham? Then choose one of the 227 places to stay that comes with a parking spot included. 16 places to stay have a a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in any of 65 accommodations that are designated as pet-friendly.

We combine a wide variety of Windham accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 159 places to stay from Airbnb, 40 accommodations from Homeaway and 39 places to stay from VRBO.

283 accommodations in Windham have been reviewed; 73% are rated highly. 126 accommodations allow instant booking.

Destinations near Windham

  1. Vacation Rental Search
  2. United States of America
  3. New York
  4. Windham