Windham vacation rentals

We found 1,221 vacation rentals — enter your dates for availability

Select from 31 homes, 12 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.

Vacation rentals with weekly discounts - Windham

Showing deals for:Nov 14 - Nov 21
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Find out more about Windham

Find out more about Windham

Why visit Windham

  1. Outdoor Adventures: Windham is ideal for hiking, fishing, and enjoying the stunning natural scenery.
  2. Charming Neighborhoods: Explore friendly areas like Water Street and Redbank Village, filled with local charm.
  3. Historic Attractions: Discover historic colleges, universities, and charming houses that reflect the region's rich history.
  4. Family-Friendly Activities: Enjoy a variety of activities suitable for all ages, ensuring fun for the whole family.
  5. Cozy Accommodations: Choose from a range of lodgings, including vacation homes, cottages, and stylish condos for a unique stay.

Popular types of accommodation in Windham

Planning a getaway to Windham? You've made a fantastic choice! Discover the perfect place to stay with our selection of popular accommodations, including houses, cozy cottages, and stylish condos. Whether you're looking for charming apartments for rent, spacious houses, or unique home rentals, Windham has something for everyone. Explore our rentals today and find the ideal spot to make your vacation unforgettable!

  • Houses: The top choice for visitors in Windham, offering spacious living and a home-like atmosphere, perfect for families and groups.
  • Cottages: A charming option, these cozy retreats provide a quaint escape amidst nature, ideal for a relaxing getaway.
  • Condos: A convenient choice for travelers, condos combine modern amenities with a great location, suitable for short or extended stays.
  • Apartments: Offering flexibility and comfort, apartments are a popular option for those seeking a more urban vibe during their stay.
  • Cabins: Ideal for nature lovers, cabins provide a rustic experience with all the comforts, perfect for a serene vacation.**

Top attractions near Windham

Windham, Maine, is perfect for those seeking outdoor adventures, scenic views, and romantic getaways. Visitors can explore a variety of attractions, including historic colleges and universities, charming historic houses, and entertainment arenas. Whether you're looking for cultural experiences, family-friendly activities, or simply a chance to enjoy nature, Windham offers something for everyone to enjoy during their stay.

  1. University of New England: A modern college with vibrant city vibes, located 7 miles from Windham. Its state-of-the-art facilities and engaging campus life make it a great spot for a leisurely stroll.
  2. University of Southern Maine: This historic college, located 9 miles from Windham, offers rich cultural experiences with its beautiful architecture and art events that reflect the area's heritage.
  3. Cross Insurance Arena: Situated 10 miles from Windham, this entertainment facility provides family-friendly events and concerts, making it a hub for local entertainment and sports.

Things to do recommended for couples

For a romantic getaway in Windham, enjoy a concert at Thompson's Point, indulge in luxury at Gorham Country Club, or embark on an adventure with water sports at Capt Lyman Stuart. Each offers a unique vibe perfect for couples seeking memorable experiences.

Things to do recommended for families

During your family vacation in Windham, enjoy exciting adventures at Seacoast Adventure, catch a game at Hadlock Field, and unwind at Fore River Sanctuary for some relaxation. These kid-friendly spots offer fun experiences perfect for creating lasting memories together!

What do I need to keep in mind when booking a vacation in Windham

If you're traveling with a group, as a family, with pets, or planning an extended stay, be sure to use the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Windham with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group activities. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Windham with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windham: For many, a family vacation isn't truly complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windham: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Windham

Windham, Maine, offers a scenic backdrop for outdoor adventures and romantic getaways. Explore charming neighborhoods like Water Street and Redbank Village, where friendly locals welcome you with open arms. Venture into nearby cities for a taste of urban life and family-friendly excursions. Whether you seek relaxation or excitement, Windham provides a perfect blend of experiences, ensuring a memorable vacation in this beautiful region of New England.

  • Portland: Located 10 miles from Windham, Portland is a vibrant city known for its stunning outdoor spaces and family-friendly activities. The waterfront area is particularly popular, offering scenic views and access to beaches that are perfect for a day of relaxation or fun in the sun. Visitors can enjoy a variety of entertainment options, including theaters and arenas, making it a great spot for a night out. Don’t forget to explore the local shopping malls, where you can find unique boutiques and delicious dining options that showcase the city's culinary scene.
  • Westbrook: Just 6 miles away from Windham, Westbrook is a charming city that offers a perfect blend of outdoor adventures and romantic settings. The city is known for its picturesque lakes and family-friendly beaches, making it an ideal destination for couples and families alike. With several shopping centers and educational venues, Westbrook provides ample opportunities for leisure and learning. Strolling through the scenic parks or enjoying a lakeside picnic can be a delightful way to spend your day in this welcoming community.
  • Gorham: Also located 6 miles from Windham, Gorham is a city that captivates visitors with its beautiful landscapes and outdoor activities. Known for its scenic trails and ski fields, Gorham is a great destination for outdoor enthusiasts looking for adventure. Whether you’re interested in skiing during the winter or hiking in the warmer months, Gorham has something for everyone. The nearby lakes and family beaches add to its charm, making it an excellent spot for a romantic getaway or a fun family outing.

Best time to go to Windham

If you're planning a trip to Windham, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January24.6°F (-4.1°C)Light RainMostly SunnyAverageSlightly Low
February25.9°F (-3.4°C)Light RainMostly SunnyAverageSlightly Low
March32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
April43.7°F (6.5°C)Light RainMostly CloudySlightly HighAverage
May54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
June62.6°F (17.0°C)Light RainMostly SunnySlightly HighSlightly High
July69.4°F (20.8°C)Light RainMostly SunnySlightly HighSlightly High
August68.7°F (20.4°C)Light RainMostly SunnyAverageSlightly High
September62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
October51.6°F (10.9°C)Light RainMostly SunnySlightly LowAverage
November40.1°F (4.5°C)Light RainMostly SunnySlightly LowAverage
December31.6°F (-0.2°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you eager to save on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your travel needs!

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner has its perks! When you join our travel rewards program, OneKey, you’ll gain immediate access to member discounts and the opportunity to earn and utilize OneKeyCash™ on qualifying bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform to help you plan new trips, resume your previous arrangements, or manage your travel plans effectively. You can easily find your saved or booked properties organized under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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.