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Destination guide

You'll find the finest kind of year-round fun in Windham

Just 12 miles northwest of Portland, ME, Windham is an active family destination offering year-round fun where you can enjoy nearby swimming and beaches during the summer, followed by tubing and snowboarding in the winter. Woo-hoo! With it’s cool history and close proximity to the Atlantic Ocean, it’s no wonder Windham vacation rentals tend to book up early. There's a summer festival and antiques shopping, plus if you want to explore the area, you’ll only be down the road from Portland. And of course, you can feast on Whoopie Pies and seafood of the finest kind.

Things to do

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.

Activities

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.

Weather

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.

Natural features

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.

How to get there

Traveling to and around Windham

Fly into Portland, ME (PWM-Portland Intl. Jetport), the closest airport, located 11.5 mi (18.4 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 18.3 mi (29.5 km) away.

How many vacation rentals are available around Windham, ME?

Our 2020 property listings offer a large selection of 566 vacation rentals around Windham. From 275 house rentals to 168 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Windham?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Windham:

  • Willard: 29 vacation rentals
  • Peaks Island: 47 vacation rentals
  • Pine Point: 262 vacation rentals
  • Downtown Portland: 66 vacation rentals
  • Camp Ellis: 51 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Windham?

Vrbo offers a large selection of vacation rentals near lovely places in Windham. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Seacoast Adventure: 686 vacation rentals
  • Maine Wildlife Park: 776 vacation rentals
  • Maine Mall: 1,247 vacation rentals
  • Ferry Beach State Park: 1,769 vacation rentals
  • Old Orchard Beach Station: 1,488 vacation rentals

But there are many other points of interest around Windham listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Windham?

Yes, of course. Vrbo has 275 Houses in Windham. Our other popular types of vacation rentals in Windham include:

  • Cottages: 168 rentals available
  • Cabins: 168 rentals available
  • Condos/Apartments: 98 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Windham?

Yes, you can select your preferred vacation rental with pool among our 31 vacation rentals with pool available in Windham. Please use our search bar to access the selection of vacation rentals available.

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