Windham vacation rentals

We found 804 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Windham by choosing from 152 houses, 32 condos, and other vacation rentals. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you expect for your stay, which might include parking and a washer and dryer. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Windham

Showing deals for:May 22 - May 29

Image gallery for Holiday Special! Hot tub, gourmet kitchen, Slopes 5 mins away, Come enjoy!

Tannersville Farmhouse in the summer!
10 out of 10, Exceptional, (87 reviews)
Exceptional
(87 reviews)

Holiday Special! Hot tub, gourmet kitchen, Slopes 5 mins away, Come enjoy!

Tannersville

9% off
Price is CA $1,823
CA $15,286 total
includes taxes & fees
Holiday Special! Hot tub, gourmet kitchen, Slopes 5 mins away, Come enjoy!

Find spaces that suit your style

Find out more about Windham

Why visit Windham

  • Winter sports paradise: Windham is renowned for its ski resorts, offering thrilling skiing and snowboarding opportunities.
  • Scenic waterfalls: Explore picturesque waterfalls that showcase the natural beauty of the region.
  • Outdoor adventures: Enjoy a variety of outdoor activities, including hiking, mountain biking, and fishing.
  • Charming accommodations: Choose from cozy cabins and private vacation homes for a comfortable stay.
  • Welcoming community: Experience the warmth of friendly locals in family-friendly neighborhoods like Windham Centre.

Popular types of accommodation in Windham

If you’re planning a getaway to Windham, you’ll find an array of outstanding vacation rentals to suit your needs. Our most popular options include houses, charming cabins, and cozy cottages. Each accommodation promises a comfortable stay with spacious suites, multiple bedrooms, and fully equipped kitchens, ensuring you have all the comforts of home while you explore the beauty of Windham.

  • Houses: These are the top choice for visitors to Windham, offering spacious and comfortable accommodations ideal for families and groups.
  • Cabins: Second in popularity, cabins provide a rustic charm and a serene escape for those seeking a nature-oriented getaway.
  • Cottages: A delightful third option, cottages offer a quaint and cozy atmosphere for a romantic retreat or peaceful vacation.
  • Apartments: Fourth on the list, apartments are a convenient choice for those looking for a more urban feel during their stay.
  • Chalets: Lastly, chalets present a unique blend of comfort and mountain aesthetics, perfect for a memorable getaway.**

Top attractions in and around Windham

Windham, New York, is an ideal destination for ski and adventure enthusiasts, offering a range of outdoor activities. Visitors can explore ski resorts, picturesque waterfalls, and the stunning natural beauty of nearby state parks. Whether you're seeking outdoor thrills, cultural experiences, or simply a chance to unwind in nature, Windham has something for everyone, making it a perfect getaway for families, groups, or solo travellers.

  • Windham Mountain Resort: Experience thrilling outdoor adventures at this popular ski resort, offering a range of winter sports, beautiful slopes, and stunning mountain views. Perfect for both skiing enthusiasts and families looking for fun.
  • Kaaterskill Falls: A romantic and adventurous spot, this magnificent waterfall is renowned for its scenic beauty and hiking trails, making it a must-visit for nature lovers and photographers.
  • Mountain Top Arboretum: This family-friendly arboretum features diverse plant collections, walking paths, and peaceful surroundings, ideal for a relaxing day out in nature.

Things to do recommended for couples

Windham is perfect for a romantic getaway. Enjoy skiing at Windham Mountain Resort, indulge in wine tasting at Windham Vineyards and Winery, or unwind together at Copperhood Retreat & Spa, located 24.1km away, for ultimate relaxation and wellness.

Things to do recommended for families

Families vacationing in Windham, New York, can have a blast at Zoom Flume, a fantastic waterpark located 11.3km away. With thrilling rides and family-friendly attractions, it promises a day filled with fun and adventure for all ages.

Things to do recommended for groups

Groups visiting Windham can enjoy a round of golf at the Windham Country Club or the nearby Blackhead Mountain Country Club, both offering beautiful outdoor settings. For a taste of local produce, visit Vinnie's Farm Market, where you can experience a vibrant market atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're planning a trip with a group, family, pets, or seeking extended stays, be sure to apply the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Windham with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Windham with young kids: Traveling with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about your closeness to attractions that are family-friendly.
  • Taking your pets with you to Windham: For many families, a vacation wouldn't be the same without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer amenities like 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 in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Windham

Windham, New York, is a charming destination perfect for adventure seekers and relaxation enthusiasts alike. Nestled amidst stunning mountain vistas, visitors can enjoy skiing and a variety of outdoor activities during the winter months. Nearby regions, like Windham Centre, offer a family-friendly atmosphere and friendly locals, making it an ideal getaway for those seeking both excitement and tranquility. Explore the scenic beauty and warm hospitality that Windham has to offer on your vacation.

  • Hunter: Nestled approximately 11.3km from Windham, Hunter is a charming city known for its thrilling outdoor adventures. A popular destination for skiing enthusiasts, the area boasts excellent ski resorts and well-maintained ski fields that cater to all skill levels. Beyond skiing, Hunter offers breathtaking landscapes featuring majestic mountains, serene lakes, and stunning waterfalls. The combination of natural beauty and adrenaline-pumping sports activities makes Hunter an ideal spot for both adventure seekers and nature lovers alike.
  • Hensonville: Located just 3.2km from Windham, Hensonville is a delightful city that invites visitors to explore its outdoor offerings. This area is a haven for those looking to enjoy skiing and other sports activities in a picturesque setting. With easy access to ski resorts and fields, Hensonville ensures that winter sports enthusiasts have a fantastic experience. Visitors can also appreciate the nearby mountains, lakes, and waterfalls, making it a perfect destination for hiking and photography opportunities, all while soaking in the region's natural beauty.
  • Jewett: Jewett is situated about 6.4km away from Windham and is another gem for outdoor activities. Like its neighboring cities, Jewett is celebrated for its skiing and adventurous spirit, featuring ski resorts and fields that attract many visitors during the winter months. The area is enriched with beautiful landscapes, including stunning mountains, tranquil lakes, and captivating waterfalls, providing plenty of opportunities for exploration and relaxation. Whether you're hitting the slopes or simply enjoying the scenic views, Jewett is a wonderful addition to your vacation itinerary.

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

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, use our filters to search by price, location, and type of vacation rental. We're here to help you make the most of your trip.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new getaways, pick up right where you left off, or manage your travel arrangements with ease. You can easily access the properties you've saved or booked, now organized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The tranquil 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 vacation 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

Do you want to find top things to see and do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Windham has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Mountain Trails Cross Country Ski and Snowshoe Center (9.5 mi / 15.3 km)

Exploring the natural landscape of Windham

Whether you're looking for fun outdoor activities or just want to take in the scenery, Windham is a great place to get out in nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Esopus Creek (28.1 mi / 45.3 km)

Seasonal weather in Windham

Travelers 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 7 inches and temperatures average 27°F.

Traveling to and around Windham

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

Frequently asked questions

What is the best area to stay in Windham when booking a vacation rental?
When considering a vacation 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 vacation home in Windham?
Prices for vacation 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 travelling 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.
Are there any discounts for Windham vacation 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 vacation rental accomodation in Windham?
In Windham, vacation houses are the most popular type of vacation 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 vacation 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 vacation 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 vacation home with a pool or hot tub in Windham?
In Windham, New York, there are plenty of vacation 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 vacation rentals in Windham?
A long-stay vacation 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 vacation 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 vacation rentals in Windham?
In Windham, New York, there are numerous options for remote work vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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 vacation 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 vacation rental in Windham depends on your preferences for winter sports and lively vacation festivities during peak season or a peaceful autumn escape with breathtaking views in the shoulder months.
How early should I book a Windham vacation rental?
Book your Windham vacation 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 vacation 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 vacation 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 vacation 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.

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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