Windham holiday rentals

We found 718 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Find the perfect place for you stay in Windham by choosing from 153 houses, 35 flats and other holiday rentals. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include air conditioning and a pool. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The relaxing city of Windham awaits you

Enjoy the wineries and other features of Windham. This relaxing city is known for its skiing, hiking and mountain views. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Windham

Are you looking for attractions to visit while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Windham a one-of-a-kind holiday spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Windham Mountain Resort (1.2 mi / 1.9 km)
  • Zoom Flume (7.4 mi / 11.9 km)
  • Hunter Mountain (7.4 mi / 12 km)
  • Kaaterskill Falls (12.5 mi / 20.1 km)
  • Belleayre Mountain Ski Center (17.8 mi / 28.6 km)
  • Belleayre Mountain Ski Center (18.4 mi / 29.6 km)

Exploring the natural landscape of Windham

Whether you're an active traveller or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Windham. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Kaaterskill Falls (12.5 mi / 20.1 km)
  • Belleayre Beach at Pine Hill Lake (16.8 mi / 27.1 km)
  • Overlook Mountain Trailhead (17.6 mi / 28.4 km)
  • Catskill Mountains (21.6 mi / 34.8 km)
  • Mountain Top Arboretum (8.4 mi / 13.5 km)
  • Platte Clove Preserve - Catskill Center (14.9 mi / 23.9 km)

Seasonal weather in Windham

Travellers enjoy Windham for its skiing. To make the most of the cold weather activities, you might consider visiting in March, January, December or November, when snowfall averages 27 cm and temperatures average -3°C.

Travelling to and around Windham

The nearest airport is in Hudson, NY (HCC-Columbia County), located 27.6 mi (44.4 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Windham?

The most sought-after types of holiday homes in Windham are houses. Hoping for something different? Vrbo has plenty of options to match our guests' diverse needs, so you'll see holiday properties in all sizes, and for all budgets. The ideal fit is waiting for you — find yours today.

How much does it cost to rent a holiday home in Windham?

Season, property type and length of stay are some factors that can affect the price of a holiday home. Simply add your dates of travel to find the ultimate escape. From comfy cottages to sprawling villas, all Vrbo holiday homes provide incredible value.

How much does it cost to rent a beach house in Windham?

Prices for beach houses in Windham may vary depending on the type and size of the property and when you're travelling. All you have to do is enter your travel dates into Vrbo and the number of guests to view holiday home options and prices. From there you can use our filters to narrow your search by nearby activities, amenities, ratings and more.

Are there pet-friendly holiday homes in Windham?

With 34 holiday homes that allow pets, your furry friend can join in the fun on your Windham break. Use the filter tool to search our pet-friendly holiday homes and find a stay that's pawfect on Vrbo.

Can I rent a house with a pool in Windham?

Tick the "pool" box in our filter tool and you can choose from 20 houses with private pools in Windham on Vrbo. Morning swim, afternoon splash or midnight soak? How you spend your free time is up to you when your holiday property boasts its own swimming pool.

What are popular home amenities in Windham?

A sauna, a barbecue grill and a lake view rank as the most popular home amenities in Windham. Whether you plan to travel as a party of one, with your other half or a bunch of friends, Vrbo will help you find a holiday home that matches your tastes with all the features you need.

Are there large group holiday homes in Windham?

Windham has 17 holiday homes that can cater to 10 or more people. These properties come with plenty of space to enjoy good times with your nearest and dearest.

Are there holiday homes in Windham that welcome kids?

Windham has 34 family-friendly holiday homes. And finding a stay that welcomes kids is easy with Vrbo's "Properties good for families" filter. In addition to having the whole place to yourselves, you'll get access to perks and conveniences like extra bedrooms, pools and kitchens.

What are the top attractions for families in Windham?

Keeping the kids happy during your holiday in Windham is a breeze with these family-friendly attractions:

  • Zoom Flume
  • Mountain Top Arboretum
  • Hunter Mountain

Can I find two-bedroom holiday homes in Windham?

Take off with your besties and enjoy total privacy and comfort in one of the eight two-bedroom holiday homes Windham has to offer.

Are there holiday homes with WiFi in Windham?

Whether you want to keep up with the headlines, send some emails or post a pic to social media, there are 15 holiday homes with WiFi in Windham. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.

How can I find holiday homes with air conditioning in Windham?

Windham has 16 holiday homes where you can kick back in air-conditioned comfort. To find a stay on Vrbo with this amenity, enter your dates of travel and use the filters to select the "air conditioning" box.

More Holiday Rentals ideas