Windham holiday lettings

We found 790 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Windham by choosing from 148 houses, 32 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:2 Jan - 9 Jan

Image gallery for Outdoor Movie Screen, Pond, Fire Pit, and Lux Hot Tub

Morning view from the top deck!
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Outdoor Movie Screen, Pond, Fire Pit, and Lux Hot Tub

Medusa, NY

18% off
Price is £4,634
for 7 nights, 1 cabin
£662 per night
includes taxes & fees
Outdoor Movie Screen, Pond, Fire Pit, and Lux Hot Tub

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Find out more about Windham

Find out more about Windham

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.

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.

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

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.

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 Country Club (1 mi / 1.6 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)

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 (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 best area to stay in Windham when booking a holiday rental?
When considering a holiday rental in Windham, New York, the best area to stay is the charming downtown district. This vibrant neighbourhood offers a delightful blend of local shops, eateries, and an inviting space that captures the essence of the Catskills. Staying here places you within easy reach of the Windham Mountain Resort, an excellent spot for skiing in the winter and hiking in the warmer months. The scenic beauty of the surrounding area is truly breathtaking, making it an ideal backdrop for outdoor activities.

Another appealing option is the area surrounding the Windham Path, a picturesque trail that winds through stunning landscapes. This neighbourhood provides a tranquil setting while still being conveniently close to the heart of Windham. You'll find a variety of holiday rentals here, with properties often boasting lovely views and easy access to nature.
How much does it cost to rent a holiday home in Windham?
Prices for holiday rentals in Windham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windham to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windham holiday house rentals?
You can find great discounts on house rentals in Windham on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Windham ski resort rentals?
For the best ski resort rentals in Windham, New York, travellers should consider properties in the vicinity of Windham Mountain, which is known for its excellent skiing conditions. The area around the mountain offers a range of holiday rentals, including cosy chalets and spacious cabins that are superb for families or groups. Many of these properties come equipped with amenities such as fireplaces, hot tubs, and fully equipped kitchens, allowing guests to unwind in comfort after a day on the slopes.

In Windham village itself, you'll find charming lodges and boutique rentals that provide easy access to local shops and restaurants, enhancing the overall experience. Some accommodations even feature ski-in/ski-out access, making it convenient for guests to hit the slopes early in the morning. Additionally, properties in the surrounding region often offer stunning mountain views and outdoor spaces, superb for enjoying the natural beauty of the Catskills.
What is the most popular type of holiday rental accomodation in Windham?
In Windham, holiday houses are the most prevalent type of rental accommodation, with approximately 125 available throughout the area. These properties often feature spacious layouts with multiple bedrooms, fully equipped kitchens, and large living areas, making them ideal for families or groups. Many holiday houses also come with outdoor spaces, such as decks or patios, where guests can relax and enjoy the scenic views of the surrounding mountains.
Are there any family house rentals in Windham?
In Windham, New York, travellers will find a substantial selection of family-friendly holiday rentals, with around 156 options available. This picturesque area is renowned for its outdoor activities and scenic beauty, making it an excellent choice for families. Many properties in the vicinity feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces superb for children to enjoy.

Particularly, neighbourhoods close to the Windham Mountain resort offer convenient access to skiing in the winter and hiking trails during the warmer months. Additionally, visitors can expect amenities such as Wi-Fi, laundry facilities, and sometimes even game rooms or fire pits for evening gatherings.
Can I rent a holiday home with a pool or hot tub in Windham?
In Windham, New York, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 43 options to choose from. This picturesque town, located in the Catskill Mountains, is popular for both summer and winter activities. Visitors can find rentals in various neighbourhoods, including the vibrant Windham Village, where properties offer convenient access to local shops and restaurants, as well as the nearby ski slopes.
Can I find long-stay holiday rentals in Windham?
A long-stay holiday rental in Windham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Windham?
In Windham, there are numerous pet-friendly house rentals available, with around 92 options to choose from. Many of these properties feature amenities that cater to both humans and their furry companions, such as spacious backyards, outdoor patios, and easy access to nearby trails. Travellers can expect comfortable living spaces, fully equipped kitchens, and sometimes even additional features like hot tubs or fireplaces, superb for unwinding after a day of exploring the beautiful surroundings.
Are there any remote work holiday rentals in Windham?
In Windham, New York, there is a substantial selection of remote work holiday rentals, with around 208 available options. This charming mountain town is ideal for those looking to combine work and leisure, especially with its stunning natural scenery and outdoor activities. Many properties come equipped with dedicated workspaces, including desks and ergonomic chairs, ensuring a comfortable environment for productivity. High-speed Wi-Fi is commonly available, along with additional amenities such as monitors and safe storage for your equipment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windham holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Windham with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Windham?
In Windham, popular rental amenities primarily include kitchens equipped with essential appliances such as microwaves, dishwashers, and cookware. Many of the holiday rentals are designed to provide a comfortable and self-sufficient stay, allowing guests to prepare their own meals and enjoy home-like conveniences.
When is the best time to visit Windham for a holiday rental?
January is the most popular month to visit Windham, New York, drawing winter enthusiasts eager to hit the slopes at the local ski resorts. This is part of the peak season, which runs from December through February, when the area transforms into a winter wonderland with excellent opportunities for skiing, snowboarding, and snowshoeing.

During this period, visitors can enjoy crisp temperatures averaging around -5 to 0 degrees Celsius, creating ideal conditions for outdoor activities. The picturesque landscapes, adorned with snow-covered trees, make for stunning views while you explore the charming village or venture into the nearby trails for a bit of winter hiking.

For those seeking a more relaxed experience with fewer crowds, October is a fantastic time to visit Windham. This month offers the beauty of autumn foliage, with vibrant colours painting the hillsides, and the cooler temperatures hovering around 10 degrees Celsius. It's a wonderful time for scenic drives, hiking, or simply enjoying the local shops and eateries without the hustle and bustle of peak tourist season.
How early should I book a Windham holiday rental?
Book your Windham holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windham?
In Windham, outdoor enthusiasts can take advantage of the stunning natural scenery and year-round attractions. The Windham Mountain Resort is a prominent draw, offering skiing and snowboarding in the winter, while in the warmer months, it transforms into a hub for hiking and mountain biking. Holiday rentals in the vicinity often provide easy access to the slopes and breathtaking views of the Catskill Mountains.
Can I change or cancel my Windham home rental booking on Vrbo?
To find Windham holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Windham holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More holiday ideas

More holiday ideas