Where to stay around Windham, ME?

Our 2019 property listings offer a large selection of 660 vacation rentals near Windham. From 288 Houses to 190 Cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Windham for a holiday or a weekend are on VRBO.

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:

  • Peaks Island: 57 vacation rentals
  • Camp Ellis: 44 vacation rentals
  • Willard: 53 vacation rentals
  • Downtown: 86 vacation rentals
  • East End: 66 vacation rentals

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

Can I rent Houses in Windham?

Yes, of course. VRBO has 288 Houses in Windham. Our other popular types of vacation rentals in Windham include:

  • Cabins: 190 rentals available
  • Cottages: 190 rentals available
  • Bungalows: 190 rentals available

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

Can I find a vacation rental with pool in Windham?

Yes, you can select your prefered vacation rental with pool among our 43 vacation rentals with pool available in Windham. Please use our search bar to access the selection of vacation rentals available.

    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.

    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.

    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.

    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.

    Explore destinations around Windham

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