Windham holiday lettings

We found 796 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:12 Jun - 19 Jun

Image gallery for 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Private kitchen
9.0 out of 10, Wonderful, (20 reviews)
Wonderful
(20 reviews)

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Hunter

8% off
Price is £1,060
for 7 nights, 1 chalet
£151 per night
includes taxes & fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee

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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:

  • Windham Country Club (1 mi / 1.6 km)
  • Windham Mountain Resort (1.2 mi / 1.9 km)
  • Zoom Flume (7.4 mi / 11.9 km)
  • Hunter Mountain (7.4 mi / 12 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (9.5 mi / 15.3 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:

  • 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)
  • Catskill Mountains (21.6 mi / 34.8 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, a popular area to stay is the vibrant village centre. This charming spot boasts a variety of properties, from quaint cottages to more modern accommodations, providing options for all types of travellers. The village is not only picturesque but also conveniently located near top attractions such as the Windham Mountain Resort, which is superb for skiing in winter and mountain biking in summer. Another great point of interest is the Windham Historical Society, where visitors can delve into the local history and culture.

Another appealing area is the surrounding countryside, where you can find lovely rentals located among the beautiful Catskill Mountains. This region offers a peaceful retreat, ideal for those who appreciate nature, with an abundance of hiking trails and stunning views. Staying here allows you to enjoy the tranquillity of the outdoors while still being a short drive away from the village's amenities and attractions.
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, visitors should consider properties situated close to Windham Mountain. The area features a range of accommodations, including charming lodges and spacious condos that cater to families and groups. Many of these rentals come equipped with amenities such as fully stocked kitchens, fireplaces for cosy evenings, and access to ski storage, making them ideal for winter sports enthusiasts.

Additionally, the village of Windham offers various dining options and local shops, enhancing the overall experience for travellers. Rentals near the base of Windham Mountain often provide ski-in/ski-out access, allowing guests to hit the slopes with ease. For those looking for a bit more luxury, some properties include hot tubs or saunas, great for relaxing after a day of skiing.

Beyond the skiing, the surrounding Catskill Mountains present opportunities for hiking and exploring scenic trails during the off-season, making Windham a versatile destination year-round.
What is the most popular type of holiday rental accomodation in Windham?
In Windham, holiday houses are the most popular type of holiday rental, with around 512 available throughout the area. These spacious homes are typically situated in scenic locations, providing easy access to outdoor activities and local attractions. Most holiday houses come equipped with multiple bedrooms, fully fitted kitchens, and ample living space, making them ideal for families or groups.

Additionally, there are about 128 condos available, which often feature modern amenities such as communal pools and fitness centres, superb for those seeking a more resort-like experience. Chalets, with approximately 80 options, provide a charming alpine feel, often with wooden interiors and proximity to skiing areas. Cabins, numbering around 72, offer a rustic escape, while about 60 apartments provide a convenient base for exploring the town and nearby attractions.
Are there any family house rentals in Windham?
In Windham, New York, there is an impressive selection of family-friendly holiday rentals, with around 157 properties available. This picturesque area, known for its stunning mountain views and outdoor activities, offers a variety of homes suitable for families. Visitors can find spacious rooms featuring multiple bedrooms, fully equipped kitchens for preparing family meals, and comfortable living areas great for relaxing after a day of adventure.

Many of these rentals are conveniently located near popular attractions such as Windham Mountain, where families can enjoy skiing in winter or hiking and biking during the warmer months. The charming town centre is also just a short drive away, where local shops, restaurants, and seasonal events add to the vibrant community atmosphere.

In addition, some properties may include outdoor amenities like decks or patios for enjoying the fresh air, while others might have game rooms or entertainment options to keep everyone entertained.
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 come with pools or hot tubs, with around 48 options to choose from. This picturesque area, known for its stunning mountain views and outdoor activities, features a variety of properties in neighbourhoods such as Windham village and the surrounding scenic hills.

Travellers can expect a range of amenities in these rentals including private swimming pools, relaxing hot tubs, and spacious outdoor areas great for entertaining or unwinding after a day of exploring. Many properties also offer fully equipped kitchens, comfortable living spaces, and proximity to local attractions such as hiking trails and ski resorts, making them ideal for families or groups seeking both relaxation and adventure.
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, offering a variety of amenities to accommodate both travellers and their furry companions. Many of these properties feature spacious layouts, fully equipped kitchens, and outdoor spaces such as decks or gardens where pets can enjoy the fresh air.

The area is known for its beautiful mountain scenery and outdoor activities, making it an ideal destination for pet owners. Nearby attractions like the Windham Mountain Resort provide opportunities for hiking and skiing, and there are several parks in the vicinity where pets are welcome to explore.

With 96 pet-friendly holiday rentals to choose from, visitors can find options that suit their needs, whether they are looking for a cosy cabin or a larger home suitable for families.
Are there any remote work holiday rentals in Windham?
In Windham, New York, there are numerous options for remote work holiday rentals, with around 872 properties available to choose from. This quaint mountain town is ideal for those looking to combine work and leisure amidst stunning natural scenery. Many of these rentals come equipped with essential amenities such as high-speed Wi-Fi, allowing for seamless connectivity while working remotely.

Travellers can expect a variety of accommodations, from cosy cabins to spacious homes, often featuring dedicated workspaces or quiet areas great for setting up a home office. Furthermore, many properties include additional comforts like fully stocked kitchens, ample living space, and sometimes outdoor areas for relaxation after a day of work.

Windham is also known for its beautiful landscapes, including nearby hiking trails and ski slopes, offering plenty of opportunities to unwind and recharge after work hours. 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 holiday rentals typically feature a range of amenities that enhance the comfort and convenience of guests. Most properties come equipped with kitchens, allowing travellers to prepare their own meals after a day of exploring the area's natural beauty. Many rentals also include a fireplace, great for creating a warm and inviting atmosphere during cooler months. Outdoor spaces such as decks or patios are common, providing a lovely setting for relaxation or al fresco dining while enjoying scenic views. Onsite parking is often available, making it easy for visitors to access the surrounding attractions. Additionally, many rentals offer coffee and tea makers, ensuring guests can enjoy their morning brew before heading out to explore nearby points of interest like the Windham Mountain Resort and the picturesque hiking trails in the Catskills.
When is the best time to visit Windham for a holiday rental?
January is the most popular time to visit Windham, perfectly aligning with the peak season that runs from December through February. This winter wonderland attracts visitors looking for exhilarating outdoor activities, particularly skiing and snowboarding, as the region is known for its excellent slopes and picturesque scenery. The cold, crisp air and snow-covered mountains create an ideal environment for those seeking adventurous winter sports.

During January, you can expect daytime temperatures to hover around -7 to 1 degrees Celsius, making it a comfortable time for both skiing enthusiasts and those who enjoy relaxing by a warm fireplace after a day on the slopes. The charming town also offers a variety of local shops and eateries, allowing visitors to immerse themselves in the cosy winter atmosphere.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a wonderful opportunity to witness the stunning fall foliage, with vibrant colours painting the landscape. It's a quieter time, great for gentle hikes and exploring the area's natural beauty without the crowds, allowing you to fully appreciate the serene surroundings.

Ultimately, the best time to book a holiday rental in Windham depends on your preferences for winter sports and lively holiday festivities during peak season or a peaceful autumn escape with breathtaking views in the shoulder months.
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, New York, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The Windham Mountain Resort is a major draw, offering skiing and snowboarding in winter, while in the warmer months, it transforms into a hub for mountain biking and hiking trails with stunning views of the Catskills.

The charming village centre features quaint shops, local eateries, and the historic Windham Theatre, where guests can catch live performances. For those interested in history and culture, the Windham Historical Society offers insights into the area's past.

Nature enthusiasts will appreciate the nearby Kaaterskill Falls, a short drive away, providing picturesque hiking opportunities and breathtaking scenery.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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