Windham holiday lettings

We found 779 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Windham by choosing from 148 houses, 33 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.

Holiday rentals with weekly discounts - Windham

Showing deals for:17 Oct - 24 Oct

Why visit Windham

  • Thrilling Skiing: Experience the exhilarating slopes of Windham Mountain, a top destination for skiing and snowboarding enthusiasts.
  • Scenic Waterfalls: Discover picturesque waterfalls that showcase the area’s natural beauty, perfect for photography and relaxation.
  • Cultural Experiences: Explore local cultural attractions, including the charming Windham Town Hall and the historic Windham Country Club.
  • Outdoor Adventures: Engage in various outdoor activities, from hiking in the nearby national state park to exploring friendly neighbourhoods.
  • Diverse Accommodation: Choose from a range of holiday rentals, including cosy cabins and charming cottages, to suit every traveller's needs.

Popular types of accommodation in Windham

Discover an array of holiday rentals in Windham, where you can choose from charming houses, cosy cabins, and delightful cottages. Whether you're seeking a spacious house rental for a family getaway or a snug apartment for a romantic retreat, Windham has the perfect accommodation for every traveller. Enjoy the convenience of our transparent listings, ensuring you find the ideal holiday lettings to suit your needs.

  • Houses: The top choice for visitors to Windham, these homes offer the perfect setting for families, couples, or groups seeking comfort and privacy.
  • Cabins: A popular option for those who love the outdoors, these rustic retreats provide a peaceful escape amidst nature.
  • Cottages: Ideal for a snug getaway, these charming properties exude character and warmth.
  • Chalets: These picturesque lodgings offer a touch of alpine elegance and stunning views.
  • Apartments: A convenient choice for shorter stays, providing all the essential amenities for a self-catering experience.**

Top attractions in and around Windham

Windham, New York, is an ideal destination for skiing and adventure sports enthusiasts. Visitors can explore local highlights such as ski resorts, picturesque waterfalls, and the nearby national state park. The area also offers cultural experiences and outdoor activities, with additional points of interest like the Windham Country Club and Windham Town Hall. Whether you're seeking thrilling adventures or serene landscapes, Windham has something for every traveller.

  • Windham Mountain Resort: A premier ski resort boasting a range of winter sports, scenic slopes, and outdoor activities. Whether skiing, snowboarding, or enjoying summer mountain biking, the resort offers thrilling adventures amidst stunning landscapes.
  • Kaaterskill Falls: A majestic waterfall located 7.5km from Windham, renowned for its natural beauty and romantic setting. Ideal for hiking enthusiasts, it provides breathtaking views and a sense of adventure in a tranquil atmosphere.
  • Mountain Top Arboretum: Situated 5.0km away, this beautiful arboretum is perfect for families, featuring diverse plant collections and serene walking paths. It's an excellent spot for nature lovers to explore and enjoy the outdoors.

Things to do recommended for couples

For a romantic getaway in Windham, indulge in skiing at Windham Mountain Resort, explore the charm of Windham Vineyards and Winery, or take a scenic ride on the Kaatskill Flyer Ski Lift, just 4.3km away. Each offers delightful outdoor experiences perfect for couples.

Things to do recommended for families

Families will have a splashing good time at Zoom Flume, a waterpark located 4.3km from Windham. With thrilling rides and family-friendly attractions, it promises a day full of adventure and entertainment for all ages.

Things to do recommended for groups

Groups visiting Windham can enjoy a round of golf at Windham Country Club or the nearby Blackhead Mountain Country Club. For a cultural experience, catch a performance at Mount Tremper Arts, perfect for family outings and romantic evenings.

Booking with Vrbo is simple

Are you hoping to make your next trip more affordable? Consider being flexible with your travel dates, as this can often lead to better pricing. Additionally, you may enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, please utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Windham

Windham, New York, is a charming destination perfect for skiing and outdoor adventures, offering a relaxing atmosphere amidst stunning scenery. Explore the friendly neighbourhoods and secluded spots nearby, where family-friendly vibes abound. Don't miss the exhilarating slopes of Windham Mountain or the picturesque homes in the area. Whether you seek thrill or tranquility, Windham promises a delightful escape for all types of travellers.

  • Hunter: Situated approximately 4.3km from Windham, Hunter is renowned for its exhilarating outdoor activities, particularly skiing. Nestled in the stunning Catskill Mountains, this charming city offers adventure seekers a plethora of options, from ski resorts to expansive ski fields. In addition to winter sports, visitors can explore the picturesque landscapes featuring mountains, tranquil lakes, and stunning waterfalls. Whether you’re carving down the slopes or enjoying a scenic hike, Hunter is a perfect destination for thrill-seekers and nature lovers alike.
  • Hensonville: Hensonville lies a mere 1.2km from Windham, making it an easily accessible haven for those seeking an active getaway. Like its neighbours, Hensonville is famed for its skiing and adventure sports, with numerous ski resorts and fields available. The surrounding natural beauty is captivating, featuring majestic mountains, serene lakes, and breathtaking waterfalls. This small city is an ideal spot for outdoor enthusiasts looking to indulge in winter sports or simply enjoy the stunning scenery that the Catskills have to offer.
  • Jewett: Just 2.5km from Windham, Jewett is another delightful destination for those eager to embrace the outdoors. With a strong emphasis on skiing and adventure sports, this city boasts easy access to ski resorts and fields. The area is rich in natural attractions, including spectacular mountains, peaceful lakes, and stunning waterfalls. Jewett is perfect for anyone looking to experience the thrill of winter sports or explore the serene beauty of the Catskill region throughout the year.

Best time to go to Windham

If you're planning a trip to Windham, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from December to February, while off-peak times, like May to June and October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.1°F (-5.5°C)Light RainMostly CloudySlightly HighSlightly High
February24.1°F (-4.4°C)Light RainMostly CloudySlightly HighSlightly High
March31.6°F (-0.2°C)Light RainMostly CloudyAverageSlightly Low
April43.3°F (6.3°C)Light RainMostly CloudyAverageSlightly Low
May55.6°F (13.1°C)Light RainMostly SunnySlightly LowSlightly Low
June63.0°F (17.2°C)Light RainMostly SunnySlightly LowAverage
July68.7°F (20.4°C)Light RainMostly SunnyAverageAverage
August66.7°F (19.3°C)Light RainMostly SunnyAverageAverage
September59.9°F (15.5°C)Light RainMostly SunnyAverageAverage
October48.9°F (9.4°C)Light RainMostly SunnySlightly LowAverage
November36.7°F (2.6°C)Light RainMostly SunnyAverageAverage
December28.8°F (-1.8°C)Light RainMostly CloudySlightly HighSlightly High

What do I need to keep in mind when booking a vacation in 'Windham

When planning your trip, whether you're travelling with a group, family, or pets, or if you're seeking longer stays, be sure to use the appropriate filters to meet your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Windham with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Windham with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, as well as seek out facilities that cater to their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windham: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Windham: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or even a private pool in your search.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you last stopped, and keep your travel arrangements well-organised. You'll find your saved or booked properties neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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:

  • Hunter Mountain (7.4 mi / 12 km)
  • Windham Mountain Resort (1.2 mi / 1.9 km)
  • Windham Vineyards and Winery (3.4 mi / 5.4 km)
  • Zoom Flume (7.4 mi / 11.9 km)
  • Kaaterskill Falls (12.5 mi / 20.1 km)
  • Indian Head Mountain (14.2 mi / 22.9 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:

  • Catskill Mountains (21.6 mi / 34.8 km)
  • Mountain Top Arboretum (8.4 mi / 13.5 km)
  • 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)
  • East Branch Delaware River (23 mi / 37.1 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 January, March, December or November, when snowfall averages 18 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 rental accommodation in Windham?
The most sought-after types of holiday rentals 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 rental 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 rentals 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 rental 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 rentals in Windham?
With 34 holiday rentals 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 rentals 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 rental amenities in Windham?
A sauna, a barbecue grill and a lake view rank as the most popular rental 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 rental that matches your tastes with all the features you need.
Are there large group holiday rentals in Windham?
Windham has 17 holiday rentals 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 rentals in Windham that welcome kids?
Windham has 34 family-friendly holiday rentals. 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 rentals in Windham?
Take off with your besties and enjoy total privacy and comfort in one of the eight two-bedroom holiday rentals Windham has to offer.
Are there holiday rentals 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 rentals with air conditioning in Windham?
Windham has 16 holiday rentals 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.
How old do you have to be to rent a holiday rental in Windham?
We advise checking with the Windham holiday property you want on Vrbo as the minimum age differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Windham for?
It all depends on the Windham property. To view a list of options offering extended stays, just enter your travel dates and number of people into Vrbo's search page. Look forward to having the whole place to yourself, as well as amenities such as a full kitchen, air conditioning and outdoor spaces to play in. Be on the lookout for long-term stays that offer discounted weekly or monthly prices.

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