Windham vacation rentals

We found 1,150 vacation rentals — enter your dates for availability

Select from 30 homes, 11 cottages, and other vacation rentals in Windham to find one that's perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, like WiFi and cable TV. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.
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Travel to friendly Windham

The lake and other outdoor surroundings create an inviting atmosphere in Windham. This welcoming city allures visitors with its restaurants and shopping. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Bygones, a brewery, and beaches with cross-country skiing?

Where to start? History buffs are sure to love 19th-century treasures including Jillson House Museum, Goold House, and a replica of an original covered bridge. Energize yourself with Whoopie Pies before heading off to Crescent Beach State Park in nearby Cape Elizabeth along the Atlantic Ocean, where you can soak up the rays on the beach, or go off-season hiking and cross-country skiing. Yes that's right - you can cross-country ski by the beach. With ocean views. And you're just down the road from Allagash Brewery Company and the Portland Museum of Art.

We'll keep you running around from dawn until dusk

Windham is a cool town where you can shop for antiques or take a cooking class in the morning, and then try your hand at fly fishing along the Pleasant River in the afternoon. You can tackle the ropes course, go tubing and splash in the water park at Seacoast Adventure, or fly 100-feet high above the ground on the Sky Swing. And in winter, Seacoast Snow Park offers snowboard lessons and a 5-acre park for practicing. Every June, Windham Summerfest hosts a parade, a car show, and entertainment, along with seafood vendors and fireworks.

4 seasons & 4 ways to play outdoors year-round

For the complete Maine experience, summer is the most popular time to visit Windham as events and activities are in full swing, and temperatures reach the high 70s. Or you could say winter is best, when everyone hits the slopes, taking advantage of the 75 inches of snowfall. Or, then again, it may be the budding flowers in the spring, or maybe it's the colorful autumn foliage. Whatever, never mind. Any time of year is a great time to visit Windham. But typically, you'll still find lower prices when booking Windham vacation rentals in the off season. Whenever that is.

Bobcats, eagles, and white-tailed deer

With a population of just over 17,000 residents, Windham, ME, was founded way back in 1762. With it's close proximity to Portland and the Atlantic Ocean, it’s not surprising that Windham vacation rentals are so popular! Nature lovers can check out bobcats and white-tailed deer at Maine Wildlife Park in Gray, just 14 miles up the road apiece, or the sandy swimming beach and a bird population which includes bald eagles at Dundee Park, set along the Presumpscot River. Or take a guided tour at nearby Sebago Lake Ecology Center where you can learn all about the Common Loon.

Transportation to and around Windham

The nearest airport is in Portland Intl. Jetport Airport (PWM), located 8.9 mi (14.3 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 20.8 mi (33.5 km) away.

Frequently asked questions

What is the best area to stay in Windham when booking a vacation rental?
Among the more popular areas to get a Windham vacation home is North Windham. When you book your vacation property with Vrbo, you can look forward to having the entire place to yourself. That means you won’t have to share it with anyone except for your favorite people.
What is the most popular type of vacation rental accommodation in Windham?
Cottages are the most popular style of vacation rental in Windham, according to our data. Even if you’ve got something bigger or smaller in mind, Vrbo has vacation homes in a variety of sizes and shapes. Explore our options to find your ideal match.
How much does it cost to rent a vacation rental in Windham?
Several things affect the price of a vacation rental in Windham, including the length of stay, type of property and season. Still, all of our vacation homes have one thing in common — unbeatable value. Just enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Windham?
Prices for beach houses in Windham can vary depending on the style and size of the property and time of year you’re traveling. Just enter your travel dates into Vrbo and the number of guests to see available options and prices. From there you can use our filters to tailor your search by ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Windham?
With 45 properties that allow pets, your happy hound can join you on your Windham getaway. Use our filter tool to search our pet-friendly vacation rentals and find your pawfect digs on Vrbo.
Can I rent a house with a pool in Windham?
Add a whole other level of fun to your getaway by booking your family into one of the two houses with a private pool in Windham. Use our handy search filter to find the kind of property you want on Vrbo, and then spend your downtime playing and splashing in a swimming pool that’s exclusively for you.
What are popular rental amenities in Windham?
Tennis, a garden and ski-in/ski-out facilities rank as the most popular rental amenities in Windham. Whether you plan to go as a party of one, with your sweetheart or as a family, Vrbo will help you find a vacation rental that matches your tastes with all the features you need.
Are there large group vacation rentals in Windham?
Windham has seven vacation rentals that can cater to 10 or more people. These properties come with all the space you need to share good times with loved ones.
Are there vacation rentals in Windham that welcome kids?
Windham has 45 family-friendly vacation homes to choose from. And tracking down a stay that welcomes kiddos is simple with our “Properties good for families” filter. Besides having the whole place to yourselves, you’ll get access to perks and conveniences like multiple bedrooms, kitchens and yards.
What are the top attractions for families in Windham?
There’s no space for boredom during your Windham trip with these family-friendly attractions to explore:

  • Maine Wildlife Park
  • Seacoast Adventure

Are there one-bedroom vacation rentals in Windham?
You’ll find three one-bedroom properties in Windham to select from. A one-bedroom vacation property is a wonderful choice if it’s just you and your sweetheart or if you’re traveling on your own. Toss in more privacy, convenience and space compared to a regular hotel, and you’ve got yourself an unforgettable getaway.
Can I find two-bedroom vacation rentals in Windham?
Take off with your besties and enjoy total privacy and comfort in one of the 11 two-bedroom vacation homes Windham has to offer.
Are there vacation rentals with WiFi in Windham?
Whether you’d like to stay in touch with the news, send a few emails or update your social media accounts, there are 23 vacation homes with WiFi in Windham. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Windham?
Windham has 32 vacation rentals where you can relax in air-conditioned comfort. To locate a stay on Vrbo that provides this amenity, enter your travel dates and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Windham?
The minimum required age is usually 16, 18 or 21. It can vary between properties on Vrbo, so look at the rules of your preferred Windham stay before booking.
How long can I rent a vacation rental in Windham for?
The amount of time you can rent a Windham vacation home for depends on the property. Simply put in your preferred travel dates to see available options that offer extended stays. They feature the things you need to make your extended break more enjoyable such as kitchens and backyards. Some properties might also offer discounted weekly or monthly prices, so you can stay longer for less money.
Does Vrbo offer discounts for vacation homes in Windham?
On Vrbo, we’ve got some fabulous discounts and deals for Windham. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re off on a weekend getaway or an extended escape, Vrbo offers lots of options for all styles and budgets.

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