Windham vacation rentals

We found 683 vacation rentals — enter your dates for availability

Discover a selection of 7 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.
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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. 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)
  • 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 (5 mi / 8 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)
  • Dorsey Park (15.3 mi / 24.6 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)

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 most popular type of vacation rental accommodation in Windham?
Based on our data, chalets are considered the most popular property type in Windham. But as you might expect, everyone’s idea of an epic trip isn’t the same. Vrbo has vacation rentals in a variety of sizes and shapes, and we’ll help you locate the best fit for your needs.
How much does it cost to rent a vacation rental in Windham?
A number of things can influence how much you pay for a vacation rental in Windham, such as the season, type of property and length of stay. However, all of our vacation homes have one thing in common — incredible value. Simply add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Windham?
Prices for beach houses in Windham may differ depending on the style and size of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and how many guests to view your rental options and prices. From there you can use the filters to narrow your search by nearby activities, amenities, ratings and more.
Are there pet-friendly vacation rentals in Windham?
Yes. There are. You’ll have a choice of eight vacation rentals that allow pets in Windham. Lots of our pet-friendly vacation rentals even have an area outdoors for your four-legged fur baby to play in, dog beds, complimentary treats and proximity to parks and green space. Apply the “Pets allowed” filter to find your pawfect vacation home on Vrbo.
Can I rent a house with a pool in Windham?
Dig out your swimsuit and inflatable flamingo, because there are two houses with a private pool in Windham. Base yourself at one of these terrific vacation homes and every day will be a pool day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find a place to make a splash!
What are popular rental amenities in Windham?
The most popular rental amenities guests are looking for in Windham are a swimming pool, a nearby waterfront and ski-in/ski-out facilities. Whether you’re taking a trip with pals, family or even pets, Vrbo vacation properties feature the best amenities for chilling out with the people who matter most.
Are there large group vacation rentals in Windham?
With three properties that can sleep 10 guests or more in Windham, you don’t have to keep your invite list short. From family get-togethers to special events like Christmas and birthday parties, Vrbo can help you find a large group rental to suit the occasion.
Are there vacation rentals in Windham that welcome kids?
Bring the entire group together for the adventure of a lifetime in Windham at one of our eight family-friendly vacation homes. Many of these stays come with amenities that are suitable for getaways with youngsters, like full kitchens, extra bedrooms and swimming pools. Simply click on the “Properties good for families” filter and select your favorite.
Are there vacation rentals with WiFi in Windham?
Pick from five vacation rentals with WiFi in Windham. If you want to disconnect from the world on your vacation, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Windham?
Pick from five vacation rentals with air conditioning in Windham offering that cooling breeze and extra level of comfort. Enter your desired travel dates and then use our handy filters to help you find properties with air conditioning.
How old do you have to be to rent a vacation rental in Windham?
The minimum age allowed can differ across properties on Vrbo, so be sure to look at the rules of the vacation home in Windham you’re interested in. But in general, it’s 16, 18 or 21.
How long can I rent a vacation rental in Windham for?
How long you can book a vacation rental in Windham is down to the property. Just enter your chosen dates to view a list of options offering extended stays. With tons of amenities such as full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to find a terrific place to call your home away from home in Windham.
Does Vrbo offer discounts for vacation homes in Windham?
On Vrbo, we’ve got some great discounts and bargains for Windham. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re planning a weekend getaway or an extended stay, Vrbo offers a variety of options for all styles and budgets.

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