Windham Vacation Rentals

Our Favorite Vacation Rentals in Windham

  • PENTHOUSE w/ SunRoom, deck, Mt view
     Home/Apartment
    Booking.com
    From
    $225
  • Spacious House - 1 Mi. to Windham Ski Resort!
     5br Home/Apartment
    HolidayLettings
    From
    $773
  • Tentrr - Pleasant Valley Maplecroft Camp
     Country House
    Booking.com
    From
    $157
  • NEW! Condo w/Loft: 2 Miles to Windham Mountain Ski
     3br Home/Apartment
    HolidayLettings
    From
    $315
  • Hunter near Ski Slopes, Catskills Amazing Views!
     Country House
    Booking.com
    From
    $535
  • Beautiful apartment with great views!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $231
  • Tentrr - Moon Song Farm
     Country House
    Booking.com
    From
    $119
  • Secluded Charming Water Front Log Home
    Good4br Home/Apartment
    HolidayLettings
    From
    $658

Check prices for these upcoming dates

Windham Vacation Rentals with a Pool

  • Cozy Condo- Windham, NY
    ExcellentHome/Apartment
    Airbnb
    From
    $167
  • Mountain View Retreat ✦ Picturesque and Peaceful
    Excellent2br Home/Apartment
    Airbnb
    From
    $249
  • Caracas Top neighborhood Apartment
     Home/Apartment
    Airbnb
    From
    $58

Windham Vacation Rentals with Wi-Fi

  • Luxury Log Home with Ski Windham Views
    Excellent5br Home/Apartment
    Airbnb
    From
    $1,694
  • Mountainside Ski Deluxe Windham Apt - 1Br 1Bath
    ExcellentHome/Apartment
    Airbnb
    From
    $276
  • Panarama House at Windham Mountain
    Excellent4br Home/Apartment
    Airbnb
    From
    $832
  • Beautiful home, mt views, hot tub, sleeps 14+, 2mi
    Excellent5br Home/Apartment
    Airbnb
    From
    $904

Windham Pet-Friendly Vacation Rentals

  • Historic Catskill Mountain House close to Windham
     7br Home/Apartment
    HolidayLettings
    From
    $887
  • NEW! Catskills Mountain Escape w/ 2 Viewing Decks
     3br Home/Apartment
    HolidayLettings
    From
    $313
  • Your Catskills basecamp
     4br Home/Apartment
    HolidayLettings
    From
    $301
  • Lovely country home in the Catskills
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $440

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
53° -7°
4
57° -8°
3
72°
1
77° 22°
4
86° 40°
3
91° 44°
5
95° 57°
4
88° 52°
4
87° 42°
2
78° 34°
7
70° 14°
3
52°
5
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Windham. The hottest month in Windham is June, when temperatures peak at 95 ˚F. The coolest month is November, when temperatures drop to -8 ˚F. The wettest month in Windham is March with 7.48 inches of rain, while the driest month is October with 1.35 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
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit

Destinations near Windham

  • New York14,494 Properties
  • Brooklyn9,337 Properties
  • Niagara Falls3,926 Properties
  • Queens2,639 Properties
  • Lake Placid1,415 Properties
  • Montauk1,410 Properties
  • Ithaca1,372 Properties
  • Sag Harbor804 Properties
  • Rochester790 Properties
  • Amagansett763 Properties
  • Lake George Village762 Properties
  • Hampton Bays664 Properties
  • Southampton660 Properties
  • Springs641 Properties
  • Ellicottville586 Properties
  • Albany551 Properties
  • Hunter547 Properties
  • Hudson540 Properties
  • Village of East Hampton525 Properties
  • Saugerties515 Properties
  • Woodstock510 Properties
  • Cooperstown473 Properties
  • Ocean Beach429 Properties
  • Canandaigua420 Properties
  • Lake George418 Properties
  • Geneva407 Properties
  • Bridgehampton391 Properties
  • Saranac Lake390 Properties
  • Beacon365 Properties
  • Kingston354 Properties
  • Penn Yan348 Properties
  • Wilmington344 Properties
  • Hammondsport337 Properties
  • Watkins Glen332 Properties
  • Cherry Grove330 Properties
  • Noyack329 Properties
  • Syracuse320 Properties
  • Staten Island319 Properties
  • Buffalo304 Properties
  • Watermill299 Properties
  • Yonkers299 Properties
  • Chestertown286 Properties
  • Alexandria Bay284 Properties
  • New Paltz277 Properties
  • East Quogue272 Properties
  • Greenport272 Properties
  • Southold262 Properties
  • Bolton Landing250 Properties
  • Long Beach245 Properties
  • Chautauqua242 Properties
  • Wainscott239 Properties
  • Warrensburg238 Properties
  • Queensbury232 Properties
  • Cortland231 Properties
  • Old Forge229 Properties
  • North Creek229 Properties
  • Binghamton220 Properties
  • White Plains214 Properties
  • Shelter Island214 Properties
  • Auburn213 Properties
  • Plattsburgh213 Properties
  • Catskill211 Properties
  • Rhinebeck211 Properties
  • Westhampton Beach202 Properties
  • Westhampton197 Properties
  • Poughkeepsie195 Properties
  • Pulaski194 Properties
  • Trumansburg194 Properties
  • Skaneateles191 Properties
  • Saratoga Springs182 Properties
  • Schroon Lake162 Properties
  • Dundee160 Properties
  • Clayton152 Properties
  • Amherst149 Properties
  • Quogue145 Properties
  • Newburgh132 Properties
  • Mount Vernon116 Properties
  • Fire Island115 Properties
  • Tupper Lake102 Properties
  • Diamond Point91 Properties
  • Fishkill88 Properties
  • Fleischmanns86 Properties
  • Millbrook61 Properties
  • Riverhead58 Properties
  • Ellenville56 Properties
  • Chatham55 Properties
  • City of Gloversville51 Properties
  • Port Jefferson39 Properties
  • Croton-on-Hudson36 Properties
  • Findley Lake33 Properties
  • Adirondack32 Properties
  • Sodus Point29 Properties
  • Washingtonville19 Properties
  • Star Lake8 Properties