Windham vacation rentals

We found 1,226 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 7 - Nov 14
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Find out more about Windham

Find out more about Windham

Why visit Windham

  1. Outdoor Adventures: Windham is ideal for nature lovers, offering hiking, biking, and scenic landscapes to explore.
  2. Charming Village Experience: Windham Mountain Village features quaint shops and restaurants that showcase local culture.
  3. Beach Access: Enjoy sun and relaxation at nearby beaches, perfect for a family day out or romantic escape.
  4. Rich History: Discover historic houses and colleges that reflect the area's cultural heritage.
  5. Welcoming Community: Experience the friendly atmosphere of Windham, making every visitor feel at home.

Popular types of accommodation in Windham

Planning a getaway to Windham? You’re in the right place! Our platform showcases the most popular types of vacation rentals, including houses, charming cottages, and modern condos. Whether you’re searching for house rentals in Windham or relaxing cottage rentals, we provide all the essential information you need for a seamless booking experience. Discover your perfect Windham vacation rental today and enjoy a memorable stay!

  • Houses: The top choice for visitors, offering spacious and comfortable living for families or groups.
  • Cottages: These charming getaways provide a cozy and quaint atmosphere, perfect for a relaxing retreat.
  • Condos: Ideal for those seeking modern amenities and convenient locations, often close to local attractions.
  • Apartments: A practical option for solo travellers or couples, providing the comforts of home.
  • Cabins: Rustic and inviting, cabins offer a unique experience immersed in nature.**

Top attractions in Windham

Windham, Maine, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. This charming area features attractions such as historic houses, entertainment arenas, and historic colleges that cater to those interested in culture and family-friendly experiences. Whether you're exploring the scenic landscapes or immersing yourself in local history, Windham offers a delightful blend of activities for every type of traveller.

  1. University of New England: A modern university located 11.3km from Windham, offering vibrant city vibes and a dynamic campus atmosphere perfect for exploring contemporary education and student life.
  2. Cross Insurance Arena: Situated 16.1km away, this entertainment facility offers a family-friendly environment with various events, including sports and concerts, making it a hub for enjoyment and excitement.
  3. St Joseph's College: A historic institution located 9.7km from Windham, showcasing rich cultural heritage and beautiful architecture, ideal for those interested in history and the arts.

Things to do recommended for couples

Planning a romantic getaway in Windham? Enjoy a captivating concert at Thompson's Point, indulge in luxury at Gorham Country Club, or embark on an adventurous day with water sports at Capt Lyman Stuart, LLC. Each experience promises unforgettable moments together.

Things to do recommended for families

Families visiting Windham can have a blast at Seacoast Adventure, an exciting arcade and adventure zone. Just a short drive away, Hadlock Field offers thrilling sports experiences, while Fore River Sanctuary provides a serene space for wellness and relaxation amidst nature.

Things to do recommended for groups

Groups visiting Windham can shop at the Maine Mall for a variety of family-friendly entertainment, enjoy a cultural experience at the State Theatre, and embark on an adventurous hike at the MAGAN Trailhead, immersing themselves in the beautiful outdoor scenery.

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

When planning your trip—whether you're travelling with a group, family, pets, or seeking extended stays—it's important to prioritise your preferences. Here are some helpful tips for booking on Vrbo.

  • Traveling to Windham with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Windham with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to take into account your closeness to attractions that are family-friendly.
  • Taking your pets with you to Windham: For many, a family getaway isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer 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 special rates for month-long stays, 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 additional features in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay in Windham

Windham, Maine, offers a delightful blend of outdoor adventures and scenic beauty, perfect for a romantic getaway or family vacation. Explore the charming Windham Mountain Village, enjoy beach access for some sun and relaxation, or venture into Southern Maine's picturesque landscapes. With friendly locals and a welcoming atmosphere, your experience in Windham promises engaging excursions and memorable moments amidst nature's splendour.

  • Portland: Located approximately 16.1km from Windham, Portland is a vibrant city known for its stunning coastal scenery and rich cultural experiences. Visitors flock to Portland for outdoor activities, family-friendly attractions, and breathtaking views. The city boasts lively theatre performances, an array of shopping options, and an impressive entertainment scene. Don't miss the chance to explore local landmarks such as the beaches, lakes, and picturesque waterfront, making it an ideal destination for those seeking both relaxation and adventure.
  • Westbrook: Just 9.7km from Windham, Westbrook offers a charming blend of outdoor romance and scenic beauty. This city is perfect for couples looking for a romantic getaway or families wanting to explore the great outdoors. Westbrook features a variety of shopping centres, making it a great spot for some retail therapy. You can also enjoy recreational activities by visiting nearby lakes and beaches. With its welcoming atmosphere and picturesque surroundings, Westbrook is a delightful area to explore.
  • Gorham: Situated a mere 9.7km from Windham, Gorham is a beautiful city that attracts those who appreciate outdoor activities and stunning landscapes. Known for its romantic ambiance, Gorham is perfect for couples and nature lovers alike. The city offers educational opportunities and is close to ski fields for winter sports enthusiasts. With scenic lakes, family-friendly beaches, and breathtaking views, Gorham is an excellent choice for a relaxing day trip or an adventurous 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 simple

Are you hoping to save on your upcoming trip? Flexibility with your travel dates can be a great way to take advantage of fluctuating prices. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you last stopped, or manage your travel arrangements. You'll see your saved or booked properties neatly organized under categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please 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.

Activities and attractions in and around Windham

Are you searching for things to do in the city? Venture out of your vacation home and experience everything that Windham has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Point Sebago Golf Resort (13.4 mi / 21.6 km)
  • Aquaboggan Water Park (14.3 mi / 23 km)
  • Funtown Splashtown USA (16.1 mi / 25.8 km)
  • Dunegrass Golf Club (16.2 mi / 26 km)
  • Pirate's Cove (17.1 mi / 27.5 km)
  • Maine Wildlife Park (5.2 mi / 8.3 km)

Exploring the natural features in Windham

Whether you're looking for adventure or just want to spend some time taking in the scenery, Windham is a great spot to appreciate mother nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Little Sebago Lake (8.4 mi / 13.5 km)
  • Thompson's Point (9.2 mi / 14.8 km)
  • Eastern Promenade (10 mi / 16 km)
  • Sebago Lake (10 mi / 16.1 km)
  • East End Beach (10.1 mi / 16.2 km)
  • Sand Beach (11.4 mi / 18.4 km)

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.
How can I find vacation rentals with air conditioning in Windham?
Windham has 30 vacation rentals where you can wind down in air-conditioned comfort. To find a stay on Vrbo that has this amenity, enter your dates of travel and use the filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Windham?
We advise checking with the Windham vacation home you're looking at on Vrbo as the age limit differs. However, it's generally 16, 18 or 21.
How long can I rent a vacation rental in Windham for?
It's up to the Windham property. To browse available options offering extended stays, simply enter your dates and number of guests into the Vrbo search page. You can enjoy having the place to yourself, along with home comforts such as air conditioning, a fully-equipped kitchen and a backyard to play in. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.
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