Windham Vacation Rentals

Our Favorite Vacation Rentals in Windham

  • PENTHOUSE w/ SunRoom, deck, Mt view
     Home/Apartment
    Booking.com
    From
    $325
  • Secluded Charming Water Front Log Home
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $859
  • Tentrr - Pleasant Valley Maplecroft Camp
     Country House
    Booking.com
    From
    $163
  • Beautiful apartment with great views!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $231
  • Hunter near Ski Slopes, Catskills Amazing Views!
     Country House
    Booking.com
    From
    $588
  • Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental
    ExcellentHome/Apartment
    HolidayLettings
    From
    $137
  • Tentrr - Moon Song Farm
     Country House
    Booking.com
    From
    $124
  • Mountain House Retreat
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $618

Check prices for these upcoming dates

Windham Vacation Rentals with a Pool

  • Windham Condo
    Good2br Home/Apartment
    Airbnb
    From
    $283
  • Caracas Top neighborhood Apartment
     3br Home/Apartment
    Airbnb
    From
    $58

Windham Vacation Rentals with Wi-Fi

  • Knollwood Acres, Windham, NY
    ExcellentHome/Apartment
    Airbnb
    From
    $107
  • Mountainside Ski Deluxe Windham Apt - 1Br 1Bath
    ExcellentHome/Apartment
    Airbnb
    From
    $311
  • Stargazers paradise
    Excellent2br Home/Apartment
    Airbnb
    From
    $325
  • Windham Mountain Retreat
    Excellent2br Home/Apartment
    Airbnb
    From
    $297

Windham Pet-Friendly Vacation Rentals

  • Historic Catskill Mountain House close to Windham
     7br Home/Apartment
    HolidayLettings
    From
    $887
  • Entire House Mountain Getaway Windham / Hunter / Belleayre / Lexington
     3br Home/Apartment
    HolidayLettings
    From
    $174
  • On A Road Less Traveled -Catskill Mountain Retreat
    Good3br Home/Apartment
    HolidayLettings
    From
    $303
  • Downtown Tannersville Apt - 3 Mi to Hunter Mtn
     3br Home/Apartment
    HolidayLettings
    From
    $366

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 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
64°
6
62° 13°
3
63° -10°
2
73°
3
56°
3
70° 19°
4
90° 41°
2
97° 48°
3
97° 51°
5
96° 57°
4
94° 43°
6
83° 27°
4
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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 use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa
  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen

Destinations near Windham

  • New York18,543 Properties
  • Brooklyn10,638 Properties
  • Niagara Falls4,945 Properties
  • Queens2,987 Properties
  • Lake Placid1,591 Properties
  • Ithaca1,574 Properties
  • Montauk1,491 Properties
  • Rochester924 Properties
  • Sag Harbor892 Properties
  • Lake George Village824 Properties
  • Amagansett792 Properties
  • Hampton Bays727 Properties
  • Southampton709 Properties
  • Springs666 Properties
  • Albany636 Properties
  • Hudson613 Properties
  • Ellicottville598 Properties
  • Lake George592 Properties
  • Woodstock589 Properties
  • Saugerties580 Properties
  • Cooperstown573 Properties
  • Village of East Hampton563 Properties
  • Hunter560 Properties
  • Canandaigua504 Properties
  • Ocean Beach451 Properties
  • Geneva444 Properties
  • Saranac Lake443 Properties
  • Kingston420 Properties
  • Bridgehampton416 Properties
  • Beacon399 Properties
  • Penn Yan387 Properties
  • Watkins Glen375 Properties
  • Chautauqua369 Properties
  • Wilmington368 Properties
  • Staten Island363 Properties
  • Hammondsport357 Properties
  • Noyack349 Properties
  • Syracuse348 Properties
  • Cherry Grove345 Properties
  • Yonkers338 Properties
  • New Paltz326 Properties
  • Watermill325 Properties
  • Buffalo318 Properties
  • East Quogue313 Properties
  • Alexandria Bay307 Properties
  • Southold299 Properties
  • Greenport299 Properties
  • Chestertown290 Properties
  • Queensbury286 Properties
  • Bolton Landing281 Properties
  • Long Beach280 Properties
  • Cortland278 Properties
  • Wainscott277 Properties
  • Warrensburg277 Properties
  • Plattsburgh274 Properties
  • Binghamton265 Properties
  • White Plains257 Properties
  • Auburn250 Properties
  • Amherst242 Properties
  • Rhinebeck241 Properties
  • Shelter Island241 Properties
  • Old Forge238 Properties
  • Poughkeepsie228 Properties
  • Catskill227 Properties
  • Westhampton Beach226 Properties
  • North Creek223 Properties
  • Skaneateles212 Properties
  • Westhampton208 Properties
  • Trumansburg208 Properties
  • Pulaski203 Properties
  • Saratoga Springs202 Properties
  • Dundee196 Properties
  • Schroon Lake191 Properties
  • Clayton169 Properties
  • Quogue157 Properties
  • Newburgh153 Properties
  • Fishkill140 Properties
  • Fire Island123 Properties
  • Mount Vernon121 Properties
  • Tupper Lake114 Properties
  • Fleischmanns94 Properties
  • Diamond Point86 Properties
  • Millbrook75 Properties
  • Riverhead67 Properties
  • Ellenville57 Properties
  • Chatham54 Properties
  • City of Gloversville53 Properties
  • Port Jefferson44 Properties
  • Findley Lake39 Properties
  • Croton-on-Hudson39 Properties
  • Adirondack30 Properties
  • Sodus Point27 Properties
  • Washingtonville22 Properties
  • Star Lake8 Properties