Windham Vacation Rentals

Our Favorite Vacation Rentals in Windham

  • PENTHOUSE w/ SunRoom, deck, Mt view
    ExcellentHome/Apartment
    Booking.com
    From
    $150
  • ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $278
  • Tentrr - Pleasant Valley Maplecroft Camp
     Country House
    Booking.com
    From
    $150
  • Secluded Charming Water Front Log Home
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $457
  • Mountain Cottage on the Creek
     Country House
    Booking.com
    From
    $231
  • Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.
     4br Chalet
    HolidayLettings
    From
    $721
  • Hunter near Ski Slopes, Catskills Amazing Views!
     Country House
    Booking.com
    From
    $458
  • Ukroatian Mountain Kucha 4 beds, 2 baths, Sleeps 12
     4br Home/Apartment
    HolidayLettings
    From
    $384

Check prices for these upcoming dates

Windham Vacation Rentals with a Pool

  • Windham Twnhse-MAKE LASTING MEMORIES
    Excellent2br Home/Apartment
    Airbnb
    From
    $364
  • Serene Family Retreat w/Indoor Pool majestic views
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,178
  • Snuggle up by the Crackling Fire at a Welcoming Ski House
    Excellent4br Home/Apartment
    Airbnb
    From
    $466
  • Mountain View Retreat ✦ Picturesque and Peaceful
    Excellent2br Home/Apartment
    Airbnb
    From
    $192

Windham Vacation Rentals with Wi-Fi

  • Brand New Windham Ski/Summer House
    Excellent4br Home/Apartment
    Airbnb
    From
    $836
  • Luxury Log Home with Ski Windham Views
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,017
  • The Windham Loft
    Excellent2br Home/Apartment
    Airbnb
    From
    $246
  • Mountainside Ski Deluxe Windham Apt - 1Br 1Bath
    ExcellentHome/Apartment
    Airbnb
    From
    $242

Windham Pet-Friendly Vacation Rentals

  • Mountain House Retreat
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $532
  • Family Fun Catskill Mountain Retreat
    Nice4br Home/Apartment
    HolidayLettings
    From
    $630
  • Historic Catskill Mountain House close to Windham
     7br Home/Apartment
    HolidayLettings
    From
    $887
  • Lakefront Windham Area Home w/ Pool, Boat & Dock!
     4br Home/Apartment
    HolidayLettings
    From
    $447

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
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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 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 Weather in Windham

Rainy days
94 º43
6
83 º27
4
64 º4
6
62 º13
3
63 º-10
2
73 º2
3
56 º7
3
70 º19
4
90 º41
2
97 º48
3
97 º51
5
96 º57
4
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Windham. The warmest months in Windham are July and June, when temperatures reach 97 ˚F. The coolest month is December, when temperatures drop to -10 ˚F. The wettest month in Windham is April with 5.62 inches of rain, while the driest month is August with 1.64 inches of rain.

What Expert Travelers Think

  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

    Monica
    MonicaNYCTechMommy
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker

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