Windham vacation rentals

We found 1,179 vacation rentals — enter your dates for availability

Select from 33 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:Apr 17 - Apr 24

Image gallery for Family & dog friendly historic 4BR farmhouse near Sebago Lake w/ boat launch!

Exterior
10 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)

Family & dog friendly historic 4BR farmhouse near Sebago Lake w/ boat launch!

Windham

16% off
Price is $332
$2,326 for 7 nights
All fees included
Family & dog friendly historic 4BR farmhouse near Sebago Lake w/ boat launch!

Find spaces that suit your style

Find out more about Windham

Why visit Windham

  • Outdoor Adventures: Enjoy a variety of outdoor activities, from hiking and biking to fishing and boating in the scenic landscapes of Windham.
  • Charming Waterfront: Explore the picturesque waterfront areas and relaxing rivers that enhance the region's natural beauty.
  • Family-Friendly Atmosphere: Windham is perfect for family outings, offering attractions that engage visitors of all ages.
  • Cultural Experiences: Visit historic sites, colleges, and entertainment venues for a taste of local culture and history.
  • Diverse Accommodations: Choose from cozy cottages, private homes, and modern condos to suit your vacation needs.

Popular types of accommodation in Windham

If you're looking for the perfect getaway in Windham, you've come to the right place. Our most popular vacation rentals include charming houses, cozy cottages, and modern condos. Whether you're searching for a comfortable base near Windham Middle School or Windham Primary School, or exploring options like single-family homes for rent, we have a variety of choices to suit your needs. Enjoy transparency, savings, and reassurance as you plan your trip.

  • Houses: This is the top choice for travelers seeking spacious accommodations perfect for families or groups, offering all the comforts of home.
  • Cottages: These quaint and cozy retreats are ideal for couples or small families, providing a charming atmosphere close to nature.
  • Condos: A popular option for those wanting modern amenities and shared facilities, perfect for a convenient stay.
  • Apartments: Offering a home-like environment, apartments are great for longer stays with everything you need at your fingertips.
  • Cabins: Rustic and inviting, cabins provide a unique getaway experience amidst beautiful landscapes.**

Top attractions near Windham

Windham, Maine, offers a perfect blend of outdoor adventures and scenic beauty, making it ideal for romantic getaways. Visitors can explore historic colleges and houses, along with entertainment arenas that provide cultural experiences. Whether you're seeking outdoor activities or a relaxing beach experience, Windham has a variety of attractions that cater to every traveler's interests, ensuring a memorable vacation.

  • University of New England: A vibrant, modern university that offers a blend of city vibes with its contemporary architecture and lively campus life. It's a great place to explore academic excellence and enjoy the energy of students and faculty.
  • Portland Museum of Art: This cultural gem features an impressive collection of American and European art. Enjoy the unique exhibitions and beautiful galleries that reflect the rich artistic heritage of the region.
  • Cross Insurance Arena: A lively venue that hosts a variety of events, from sports to concerts. It’s perfect for family entertainment, offering an exciting atmosphere that brings communities together.

Things to do recommended for couples

For a romantic getaway in Windham, consider a visit to Thompson's Point, just 9 miles away. Enjoy a lively music concert surrounded by entertainment vibes, perfect for creating lasting memories with your partner.

Things to do recommended for families

Your family will have a blast at Seacoast Adventure, an arcade adventure zone in Windham. Just a short drive away, you can catch a game at Hadlock Field or unwind in the serene surroundings of Fore River Sanctuary for a perfect mix of excitement and relaxation.

Things to do recommended for groups

Groups visiting Windham can enjoy shopping and entertainment at the Maine Mall, located 9 miles away. For outdoor adventure, hike the scenic MAGAN Trailhead just 3 miles from town. Don’t miss the iconic LL Bean Flagship Store, 16 miles away, for a unique shopping experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, or pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Windham with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Windham with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, it's wise to think about how close you'll be to attractions that are enjoyable for the whole family.
  • Taking your pets with you to Windham: For many families, a getaway wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo listings that welcome pets. Most 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 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 rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Windham

Windham, Maine, is a delightful destination perfect for outdoor enthusiasts and those seeking scenic beauty. During your visit, explore the charming waterfront areas and enjoy the pleasant rivers that define the region. The friendly atmosphere makes it ideal for family-friendly outings and romantic getaways alike. Venture into nearby southern Maine for urban excursions, where you'll find a mix of vibrant neighborhoods and warm hospitality. Experience the best of both nature and community in this great location.

  • Portland: Located 10 miles from Windham, Portland is a vibrant city known for its stunning outdoor scenery and family-friendly atmosphere. Visitors flock to Portland for its rich arts scene, featuring theaters and arena entertainment facilities, as well as a variety of shopping opportunities. The city's waterfront is a must-visit, where you can enjoy beautiful beaches and picturesque lakes. Outdoor enthusiasts will appreciate the parks and trails that invite exploration, making it a perfect destination for a fun-filled day with family or friends.
  • Westbrook: Just 6 miles from Windham, Westbrook offers a charming blend of outdoor experiences and romantic settings. This city is known for its picturesque lakes and beautiful beaches, making it ideal for leisurely strolls or picnics. Westbrook features a variety of shopping centers and educational venues that provide both entertainment and enrichment. Whether you're enjoying a serene day by the water or exploring the local shops, Westbrook is a delightful stop on your Maine adventure.
  • Gorham: Situated 6 miles from Windham, Gorham is a lovely city that combines outdoor scenery with a romantic ambiance. The area is perfect for those who love skiing and winter sports, with access to ski fields nearby. In addition to winter activities, Gorham boasts beautiful lakes and family-friendly beaches that cater to all ages. The city's educational facilities provide a unique cultural touch, making it an enriching destination for visitors seeking both adventure and relaxation.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 cut costs on your upcoming journey? Being flexible with your travel dates can really help, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly platform where you can easily plan new trips, revisit your previous work, or manage your travel arrangements. You'll find your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/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?
When considering a vacation rental in Windham, Maine, a popular area to stay is the Lakes Region, particularly around the scenic Sebago Lake. This area is renowned for its beautiful waterfront views and offers a lot of outdoor activities, making it an ideal spot for nature enthusiasts. Here, you can enjoy swimming, boating, and fishing in the summer, while the fall brings stunning foliage, superb for hiking and exploring the numerous trails.

Another attractive neighborhood is Windham's Main Street area, which provides easy access to local shops and restaurants. This vibrant area is close to the Windham Town Hall and the Windham Public Library, offering a glimpse of the local culture. You'll find a variety of vacation rentals, from cozy cabins to modern homes, which cater to different preferences and group sizes.

In terms of attractions, the nearby Sebago Lake State Park is a must-visit, featuring hiking trails, picnic areas, and scenic views of the lake. Additionally, the Windham Hill Baptist Church, with its stunning architecture, adds a touch of historical interest to your stay.
How much does it cost to rent a vacation home in Windham?
Prices for vacation rentals in Windham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windham to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windham vacation house rentals?
You can find great discounts on house rentals in Windham on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Windham?
For renting a beach house in Windham, Maine, travelers should consider the nearby Sebago Lake area, which is just a short drive away and offers a beautiful lakeside experience. The Sebago Lake State Park is a popular destination for beachgoers, and the surrounding neighborhoods feature vacation rentals that often include spacious outdoor decks, private docks, and access to swimming areas. Many properties here come equipped with amenities such as barbecue grills, fire pits, and fully stocked kitchens, making them ideal for family gatherings or group getaways.

Additionally, the Windham area itself boasts charming waterfront homes along the Presumpscot River, providing a serene setting for relaxation. These rentals may offer features like kayaks or canoes for exploring the river, along with cozy interiors that include fireplaces and comfortable living spaces. Travelers can also enjoy nearby recreational options, including hiking trails, fishing spots, and local parks.

For those looking for dining and entertainment, Windham has a selection of local eateries and shops, ensuring that all necessary conveniences are within reach. Find your rental near the beach in Windham.
Where are the best Windham ski resort rentals?
For skiing in Windham, Maine, travelers should focus on the area surrounding Windham Mountain Resort. The town itself offers a variety of rental options, including cozy cabins and modern chalets that cater to different group sizes. Many of these properties come equipped with amenities such as wood-burning fireplaces, spacious living areas, and outdoor decks superb for enjoying the winter scenery.

In the vicinity of the resort, you can find vacation rentals that provide easy access to the ski lifts, with some properties even offering shuttle services for convenience. Additionally, there are homes with ski storage facilities and heated garages, making it easy to keep gear safe and warm after a day on the slopes.

For those looking to enjoy the local experience, the nearby village of Windham features charming shops and restaurants, enhancing the overall stay. Rentals in this area often include fully equipped kitchens, allowing travelers to prepare meals after a day of skiing. The region also offers opportunities for snowshoeing and cross-country skiing, with rentals that provide easy access to trails for those interested in exploring beyond downhill skiing.
What is the most popular type of vacation rental accomodation in Windham?
In Windham, vacation houses are the most popular type of rental, with about 27 available throughout the area. These vacation houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios, allowing guests to enjoy the natural surroundings. Additionally, there are around 13 cottages, which provide a cozy, rustic feel and often include amenities like fireplaces and access to nearby lakes or hiking trails. For those seeking a more secluded experience, several cabins and villas are also available, offering a tranquil retreat with modern comforts.
Are there any family house rentals in Windham?
In Windham, Maine, there are numerous family-friendly vacation rentals available, with about 28 options to choose from. This charming town offers a variety of homes that cater to families, featuring spacious living areas, full kitchens for preparing meals, and outdoor spaces superb for kids to enjoy. Many properties come equipped with essential amenities such as Wi-Fi, laundry facilities, and air conditioning to ensure a comfortable stay.

Travelers will appreciate the proximity to local attractions, including the scenic Sebago Lake, which provides opportunities for swimming, fishing, and hiking. Additionally, the area boasts beautiful parks and recreational facilities where families can enjoy outdoor activities.
Can I rent a vacation home with a pool or hot tub in Windham?
In Windham, Maine, there are several vacation homes available for rent that feature pools and hot tubs. This picturesque area is known for its beautiful landscapes and outdoor activities, making it an excellent choice for travelers seeking relaxation and adventure. Many of the available rentals come with amenities such as private pools, hot tubs, spacious decks for outdoor gatherings, and fully equipped kitchens, allowing for both leisure and convenient self-catering during your stay.

Windham's proximity to lakes and hiking trails also enhances its appeal, providing opportunities for swimming, fishing, and exploring nature.
Can I find long-stay vacation rentals in Windham?
A long-stay vacation rental in Windham is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Windham?
In Windham, there are several pet-friendly house rentals available, making it a great destination for travelers wishing to bring their furry friends along. Many of these vacation homes offer a variety of amenities, such as spacious yards, fully equipped kitchens, and cozy living areas, ensuring a comfortable stay for both guests and their pets. The area is known for its beautiful natural surroundings, providing ample opportunities for outdoor activities with pets, including hiking and exploring nearby parks.

Additionally, Windham is close to several lakes, which can be superb for leisurely walks and playtime with pets. The local community is generally welcoming to pets, with some nearby parks and trails providing scenic routes for walking and enjoying the outdoors together.
Are there any remote work vacation rentals in Windham?
In Windham, Maine, there are approximately 40 vacation rentals that cater to remote work needs. This charming town, located near the picturesque Sebago Lake, offers a variety of properties suitable for those looking to balance work and leisure. Travelers can expect amenities such as dedicated office spaces complete with desks and ergonomic chairs, high-speed Wi-Fi, and in some cases, additional equipment like computer monitors to enhance productivity.

Many of the rentals are spacious, providing comfortable living areas that allow for relaxation after a day of work. Additionally, some properties feature outdoor spaces where guests can unwind and enjoy the natural beauty of the area. Windham is also close to recreational activities, including hiking trails and water sports, making it an ideal location for those who want to combine work with outdoor adventure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windham vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windham with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Windham?
In Windham, popular vacation rental amenities include WiFi, kitchens equipped with essential appliances, and convenient features like blenders and coffee/tea makers. Many rentals also offer kitchen islands, enhancing the cooking experience.
When is the best time to visit Windham for a vacation rental?
The best time to visit Windham, Maine, is during the vibrant summer months, particularly in July. This peak season, which spans from June to August, attracts a diverse array of travelers eager to enjoy the warm weather and the abundance of outdoor activities available in the area. With temperatures typically ranging from the mid-60s to low 80s Fahrenheit, July offers ideal conditions for hiking, boating, and exploring the scenic beauty of the region.

During this lively month, visitors can partake in the local charm and enjoy the picturesque landscapes that Windham has to offer. The nearby Sebago Lake is superb for swimming and fishing, while the surrounding trails provide ample opportunities for hiking and biking, ensuring that adventure seekers find plenty to keep them engaged.

If you're looking for a more budget-friendly option, consider planning your trip in November. While this month sees fewer tourists, it presents a unique charm with the onset of cooler weather. You can enjoy the serene beauty of the area, superb for a peaceful getaway, and take advantage of lower rental rates.
How early should I book a Windham vacation rental?
Book your Windham vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windham?
In Windham, Maine, visitors can enjoy a range of attractions that showcase the area's natural beauty and recreational opportunities. The picturesque Sebago Lake State Park offers hiking trails, swimming areas, and picnic spots, making it a great destination for outdoor enthusiasts. Nearby, the charming Windham Town Center features local shops and eateries that reflect the community's character.

For those interested in winter sports, the area is a short drive from ski resorts like Shawnee Peak, providing opportunities for skiing and snowboarding during the colder months.
Can I change or cancel my Windham home rental booking on Vrbo?
To find Windham vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Windham vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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