Windham vacation rentals

We found 1,034 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
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June 2024
Select from 32 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?

If you're considering a Windham getaway, North Windham is one of the most desired places to stay. Whether you choose a condo, cabin or another property type, you'll always have the entire place to yourself.

What is the most popular type of vacation rental accommodation in Windham?

Houses are the most popular kind of vacation rental in Windham, according to our data. Even if you have a different idea in mind, Vrbo has properties in all shapes and sizes. Filter our options to find your perfect fit.

How much does it cost to rent a vacation rental in Windham?

The average price for a vacation rental in Windham can vary depending on factors such as property type, length of stay and season. Whether you're looking for a sprawling villa with space for extended family or a quaint cabin just enough for two, just enter your travel dates to find some great-value stays.

How much does it cost to rent a beach house in Windham?

When you travel and the style and size of the property will influence the cost of your beachside vacation rental. Type in your Windham travel dates to see all your options on Vrbo. Did someone just say "private pool"? Use the filters to pick the amenities and features you want in your beach house.

Are there pet-friendly vacation rentals in Windham?

With 40 vacation rentals that host pets, your furry companion can also come along on your Windham break. Use our filter tool to search our pet-friendly vacation rentals and find your pawfect digs on Vrbo.

What are popular rental amenities in Windham?

Some of the most popular rental amenities people prefer in Windham include mountain views, a beach view and nearby museums. Whether you're going on vacation with family, pals or even pets, Vrbo vacation rentals have the best amenities for making epic memories with the people you cherish the most.

Are there large group vacation rentals in Windham?

Windham has five vacation rentals that can accommodate 10 or more guests. These properties come with all the space you need to enjoy good times with your favorite people.

Are there vacation rentals in Windham that welcome kids?

Bring the whole group together for an unforgettable adventure in Windham at one of our 40 family-friendly properties. Many of these stays provide conveniences that are great for getaways with youngsters, including dining rooms, extra bedrooms and entertainment areas. Simply check the "Properties good for families" filter box and choose your favorite option.

What are the top attractions for families in Windham?

There are plenty of fun things to see and do with the family in Windham, such as:

  • Maine Wildlife Park
  • Seacoast Adventure
  • Childrens Museum and Theatre of Maine

Are there one-bedroom vacation rentals in Windham?

You'll find three one-bedroom properties in Windham to pick from. A one-bedroom vacation home is a superb choice if it's just two of you or if you're flying solo. Add in more convenience, space and privacy than a regular hotel, and you'll be sure to have a memorable getaway.

Can I find two-bedroom vacation rentals in Windham?

Windham has nine two-bedroom vacation properties that you can choose from. Enjoy a vacation home with all the privacy and comfort you're looking for at a price that won't break the bank on Vrbo.

Are there vacation rentals with WiFi in Windham?

Whether you'd like to keep up to date with the news, reply to emails or surf social networks, there are 20 vacation homes with WiFi in Windham. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

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