Windham vacation rentals

We found 685 vacation rentals — enter your dates for availability

Discover a selection of 12 homes and other vacation rentals in Windham that are perfect for your trip. Vacation homes provide the best amenities for your family, friends, or furry companion, such as parking and a washer and dryer. At the end of the day, you'll find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Windham

Showing deals for:May 29 - Jun 5

Image gallery for the farmhouse at Big Picture Farm

Snow and ski sports
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

the farmhouse at Big Picture Farm

Townshend

14% off
Price is $1,758
$12,309 for 7 nights
All fees included
the farmhouse at Big Picture Farm

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Find out more about Windham

Why visit Windham

  • Winter sports paradise: Windham is a haven for ski enthusiasts, offering fantastic slopes and ski resorts.
  • Charming local villages: Explore nearby Windham, NY, and Manchester, known for their scenic charm and friendly atmosphere.
  • Outdoor adventures: Enjoy hiking, biking, and exploring national parks amidst stunning landscapes.
  • Diverse accommodations: Choose from cozy cabins to luxurious rentals tailored to every traveler's needs.
  • Memorable cultural experiences: Immerse yourself in the local culture while relishing the region's natural beauty.

Popular types of accommodation in Windham

Explore the charm of Windham with a variety of vacation rental options tailored to your needs. Whether you're looking for a cozy private vacation home, a convenient townhome apartment, or a rustic cabin, Windham has it all. Our platform ensures you find the perfect place to stay, with available rental units that suit every traveler's preference. Reserve your getaway in Windham County today and enjoy a memorable experience.

  • Houses: The top choice for travelers in Windham, these homes offer spacious and comfortable settings perfect for families or groups.
  • Condos: A popular option, condos provide modern amenities and easy access to local attractions, making them ideal for shorter stays.
  • Cabins: For a cozy retreat, cabins in Windham offer rustic charm and a connection to nature.
  • Apartments: Well-suited for solo travelers or couples, apartments offer a convenient and budget-friendly lodging option.
  • Chalets: These charming structures provide a unique mountain experience, perfect for enjoying the scenic views of Windham.**

Top attractions near Windham

Windham, Vermont, is an ideal destination for ski enthusiasts and adventure seekers, offering a variety of activities for outdoor lovers and families alike. With attractions such as national parks, ski resorts, and scenic parks, visitors can immerse themselves in nature while enjoying cultural experiences. Whether you're hitting the slopes or exploring the area's natural beauty, Windham promises memorable adventures for everyone.

  • Stratton Mountain Resort: Nestled 11 miles from Windham, this premier ski resort offers thrilling skiing and snowboarding experiences in winter, along with hiking and mountain biking in warmer months. It’s a perfect destination for adventure seekers, boasting stunning mountain vistas and a vibrant outdoor atmosphere.
  • Lowell Lake State Park: Located 4 miles away, this national park features picturesque scenery, making it ideal for hiking, fishing, and picnicking. Its serene lake and lush surroundings provide a peaceful escape for nature lovers and outdoor enthusiasts.
  • Ball Mountain Dam: Just 4 miles from Windham, this impressive dam showcases beautiful landscapes and serene waters, perfect for photography and leisurely walks. The surrounding area offers scenic views, making it a tranquil spot for relaxation and exploration.

Things to do recommended for couples

For a romantic getaway in Windham, embrace the winter magic at Magic Mountain Ski Resort, just 3 miles away, or enjoy outdoor adventures at Stratton Mountain Resort, 11 miles away. Don't miss the thrill of the American Express Ski Lift, located 10 miles from town, for unforgettable memories together.

Things to do recommended for families

Your family can have a blast at the Bromley Alpine Slide, just 11 miles from Windham, or unwind at Dana L. Thompson Memorial Park, located 17 miles away, which offers a serene atmosphere perfect for relaxation and wellness.

Things to do recommended for groups

Groups visiting Windham can enjoy a round of golf at Stratton Mountain Golf Course, just 5 miles away, or catch a show at the Weston Playhouse, located 9 miles away. Don't forget to browse My Minds Design, a unique store located 6 miles from Windham.

*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 traveling with a group, bringing your family, including pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist 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 group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Windham with young kids: Traveling with young kids can be quite a challenge. It's important to prioritize their comfort and safety, along with age-appropriate amenities like a private 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 families, a vacation wouldn't be the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with 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 searching for vacation rentals that offer discounts 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 rental options. Also, think about including amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Windham

Windham, Vermont, offers a delightful blend of adventure and relaxation, perfect for ski enthusiasts and sports lovers. Nearby, you can explore the charming village of Windham, NY, and the picturesque town of Manchester, renowned for its scenic beauty and friendly atmosphere. Whether you seek luxury accommodations or a romantic getaway, this region provides a captivating experience with stunning landscapes and welcoming communities to enhance your vacation.

  • Londonderry: Nestled about 6 miles from Windham, Londonderry is a charming city that attracts outdoor enthusiasts seeking thrilling adventures. Known for its excellent ski opportunities, travelers can enjoy skiing at well-maintained ski resorts and fields. The surrounding landscape offers stunning views of mountains, valleys, and lakes, making it a perfect spot for both winter sports and summer hikes. Whether you’re hitting the slopes or exploring the natural beauty, Londonderry provides a delightful escape for adventure seekers.
  • Stratton: Located 12 miles from Windham, Stratton is a popular destination for those eager to embrace the thrill of skiing and outdoor sports. With its renowned ski resorts and expansive ski fields, visitors can experience some of the best skiing in the region. The breathtaking mountains and picturesque valleys add to the allure, making it an ideal spot for both winter sports and scenic exploration. Stratton is perfect for families and groups looking to enjoy a variety of recreational activities year-round.
  • Weston: Just 9 miles away from Windham, Weston offers a quaint and scenic retreat for visitors. Known for its skiing, adventure, and sports, this city is surrounded by stunning natural landscapes, including beautiful lakes, valleys, and mountains. The ski resorts in Weston provide fantastic opportunities for skiing enthusiasts, while the charming atmosphere invites relaxation and exploration. Experience the local culture and enjoy outdoor activities that make Weston a notable destination for those looking to connect with nature.

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 in March, July and September, while off-peak times, like February, October and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.8°F (-6.8°C)Light RainMostly CloudyAverageSlightly High
February21.7°F (-5.7°C)Light RainMostly CloudyLowSlightly High
March29.7°F (-1.3°C)Light RainMostly CloudyHighAverage
April41.9°F (5.5°C)Light RainMostly CloudyAverageSlightly Low
May54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly Low
June62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
July68.2°F (20.1°C)Light RainMostly SunnyHighAverage
August66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
September59.4°F (15.2°C)Light RainMostly SunnyHighSlightly Low
October47.8°F (8.8°C)Light RainMostly CloudyLowAverage
November35.4°F (1.9°C)Light RainMostly SunnyAverageAverage
December26.8°F (-2.9°C)Light RainMostly CloudyLowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Staying flexible with your travel dates can help, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your reservation. It truly pays to take on the planning role. When you join our travel rewards program, One Key, you’ll gain immediate access to exclusive member discounts and the opportunity to earn and redeem OneKeyCash on eligible bookings. Sign up today and begin saving.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient area for you to plan new trips, keep track of your ongoing arrangements, or review and organize your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To discover Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Windham getaway

Learn about the unique charm of Windham with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Stratton Mountain Resort and Okemo Mountain Resort are just a couple of the must-sees in the area. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Windham

Do you want to discover attractions to see while you're in the area? Venture out of your cozy vacation rental and experience everything that makes Windham a one-of-a-kind vacation spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Stratton Mountain Resort (10.6 mi / 17.1 km)
  • Okemo Mountain Resort (15.8 mi / 25.4 km)
  • Magic Mountain Ski Resort (2.6 mi / 4.2 km)
  • Jamaica State Park (4.7 mi / 7.6 km)
  • Viking Nordic Center (4.7 mi / 7.6 km)
  • Stratton Mountain Golf Course (9.7 mi / 15.7 km)

Exploring the natural landscape of Windham

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Windham is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Lowell Lake State Park (4 mi / 6.5 km)
  • Winhall River (6.2 mi / 10 km)
  • Emerald Lake State Park (16 mi / 25.8 km)
  • Lye Brook Falls (16.2 mi / 26.1 km)
  • Battenkill River (16.4 mi / 26.5 km)
  • Green Mountain National Forest (16.9 mi / 27.2 km)

Transportation to and around Windham

The nearest airport is in Springfield, VT (VSF-Hartness State), located 15.5 mi (24.9 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 26.9 mi (43.3 km) away.

Frequently asked questions

What is the best area to stay in Windham, Vermont, United States of America when booking a vacation rental?
When looking for the best area to stay in Windham, Vermont, one highly recommended neighborhood is nearby Jamaica. This charming area is not only picturesque but also provides easy access to some of the region's top attractions, such as the scenic Jamaica State Park, which offers fantastic hiking trails and opportunities for enjoying nature. Additionally, the quaint downtown area features local shops and dining options that reflect the community's unique character.

Another great option is the vicinity of Stratton. Known for its world-class ski resort, Stratton attracts outdoor enthusiasts year-round. In the winter, visitors can indulge in skiing and snowboarding, while in the warmer months, activities like mountain biking and hiking take center stage. The vibrant village atmosphere, complete with shops and restaurants, adds to the appeal, making it an ideal spot for vacationers looking for both adventure and relaxation.
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 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 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.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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 travelers 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.
When is the best time to visit Windham for a vacation rental?
March is often regarded as the most popular time to visit Windham, Vermont, as it marks the tail end of the winter season and offers excellent skiing conditions for snow enthusiasts. During this month, visitors can enjoy a variety of outdoor activities, including snowboarding and snowshoeing, all set against the stunning backdrop of the Green Mountains. The average temperatures in March range from the low 20s to the mid-40s Fahrenheit, making it comfortable for outdoor adventures while still providing a winter wonderland experience.

As the peak travel season follows from July to September, travelers looking for vibrant summer activities will find this period ideal for hiking, biking, and enjoying the local festivals. The warm weather brings lush greenery and an array of recreational options, great for travelers.

For those seeking a more budget-friendly option, consider visiting in December. While this month falls into the low season, it offers a unique charm as Windham embraces the holiday spirit. Visitors can experience cozy accommodations and enjoy quieter slopes, creating a more intimate winter getaway.

Ultimately, the best time to visit Windham depends on your preference for either thrilling winter sports in March or the lively summer months filled with outdoor exploration.
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, Vermont, United States of America?
In Windham, Vermont, visitors can experience firsthand the natural beauty and recreational activities the area has to offer. The nearby Bromley Mountain is a major attraction for outdoor enthusiasts, particularly for skiing in the winter and hiking during the warmer months. The mountain features a variety of trails suitable for all skill levels, and the scenic views are breathtaking.

In addition to skiing and hiking, Windham is close to the charming town of Londonderry, where travelers can explore local shops, eateries, and the historic Weston Playhouse, which hosts various theatrical performances throughout the year.

For those who appreciate natural landscapes, the nearby Green Mountain National Forest offers stunning views and opportunities for camping, fishing, and wildlife viewing.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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