Windham vacation rentals

We found 1,197 vacation rentals — enter your dates for availability

Select from 36 homes, 11 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:Jun 12 - Jun 19

Image gallery for Cozy countryside cottage located on Crooked river in Naples Maine.

Property grounds
10 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)

Cozy countryside cottage located on Crooked river in Naples Maine.

Naples

9% off
Price is $317
$2,219 for 7 nights
All fees included
Cozy countryside cottage located on Crooked river in Naples Maine.

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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, Maine, United States of America when booking a vacation rental?
When considering a vacation rental in Windham, Maine, the area around the village center is an excellent choice. This charming neighborhood offers a blend of convenience and local flavor, making it an ideal spot for visitors. You'll find a variety of properties available, ranging from cozy cabins to family-sized homes, which cater to different group sizes and budgets.

One of the top attractions in this area is the picturesque Sebago Lake, just a short drive away, where you can enjoy swimming, boating, and picnicking in the summer months. Additionally, the nearby Windham Town Beach provides a lovely spot for relaxation and outdoor fun. For those interested in hiking or exploring nature, the area's scenic trails offer beautiful views and a chance to experience the local wildlife.

Staying in the village center not only puts you close to recreational activities but also allows easy access to local shops and restaurants, giving you a taste of Windham's welcoming community.
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 picturesque areas surrounding the Sebago Lake region. The neighborhood around the eastern shore of Sebago Lake, particularly near the town of Naples, offers a variety of vacation rentals that provide easy access to sandy beaches and recreational activities. Many properties in this area feature amenities such as private docks, outdoor decks with lake views, and spacious yards, making them ideal for families looking to enjoy summer activities like swimming and boating.

Additionally, the nearby town of Standish offers options along the Songo River, where travelers can find charming cabins and cottages that often come equipped with modern kitchens, fire pits for evening gatherings, and cozy living spaces that celebrate the natural surroundings. These rentals provide a tranquil retreat while being just a short drive from local attractions and dining options.

For those who enjoy nature, the surrounding area features numerous hiking trails and parks, including the scenic Sebago Lake State Park, where visitors can explore the beautiful landscapes and enjoy outdoor activities. Rentals in this region typically include amenities that cater to outdoor enthusiasts, such as access to trails and equipment storage for kayaks and bikes.
Where are the best Windham ski resort rentals?
For the best ski resort rentals near Windham, travelers should focus on the area surrounding the Windham Mountain Resort, which offers a variety of accommodations to suit different preferences. In the village of Windham, visitors can find cozy cabins and lodges that typically feature amenities such as wood-burning fireplaces, hot tubs, and well-equipped kitchens, making them great for relaxing after a day on the slopes. Many properties are conveniently located within walking distance to the ski lifts, ensuring easy access to the mountain.

Additionally, nearby neighborhoods like Hensonville and the Catskill State Park area offer a range of vacation rentals, including charming chalets and modern condos. These often come with outdoor spaces like decks or patios, where guests can enjoy the scenic mountain views. Some rentals may also provide complimentary shuttle services to the ski resort, enhancing convenience for those looking to maximize their time on the slopes.

For travelers interested in après-ski activities, the Windham area features local dining options and shops, making it easy to explore the community. The region's natural beauty also offers opportunities for hiking and snowshoeing during the winter months, with several properties situated close to scenic trails.
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 29 available throughout the area. These properties are often situated in peaceful neighborhoods, providing a comfortable and spacious environment for travelers. Most vacation houses come with fully equipped kitchens, cozy living areas, and outdoor spaces like decks or patios for enjoying the serene surroundings.

Additionally, there are around 10 cottages scattered around Windham, which offer a charming and rustic atmosphere, great for those looking for a more intimate stay. These cottages typically feature kitchen facilities and comfortable seating areas. While cabins, apartments, and villas are also available in smaller numbers, they provide additional options for visitors seeking different styles of accommodation.
Are there any family house rentals in Windham?
In Windham, Maine, there are some family-friendly house rentals available, with around 32 options scattered throughout the area. This charming town is well-suited for families looking for a retreat, offering spacious homes that often include amenities such as full kitchens, outdoor decks, and cozy living rooms superb for gathering after a day of activities.

Visitors can enjoy nearby attractions like the pristine Sebago Lake, ideal for swimming, boating, and picnicking, as well as local parks that feature playgrounds and walking trails. The surrounding landscapes provide ample opportunities for outdoor adventures, including hiking and exploring the scenic beauty of Maine.
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 charming town, located near the scenic Sebago Lake region, provides a peaceful retreat for travelers looking to enjoy the outdoors. Many of these properties come equipped with amenities such as private pools, hot tubs, spacious decks for outdoor lounging, and fully equipped kitchens, making them ideal for family gatherings or relaxing getaways.
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 numerous pet-friendly house rentals available, with around 24 options for travelers looking to bring their furry friends along. Many of these rentals feature spacious layouts, fully equipped kitchens, and cozy living areas, ensuring a comfortable stay for both humans and pets. Some properties may also offer outdoor spaces such as fenced yards or decks, superb for pets to enjoy the fresh air.

Windham is surrounded by beautiful natural landscapes, providing ample opportunities for outdoor activities with pets. Nearby, the Sebago Lake area is a popular spot for hiking, swimming, and picnicking, making it an ideal location for pet owners seeking adventure. Additionally, local parks often welcome pets, providing places for walks and play. See all pet-friendly rentals in Windham.
Are there any remote work vacation rentals in Windham?
In Windham, Maine, there are ample options for remote work vacation rentals, with around 42 properties available to cater to your needs. Many of these rentals come equipped with essential amenities for productivity, including high-speed internet, free Wi-Fi, and dedicated workspace areas featuring desks and chairs. This ensures that you can comfortably balance work and leisure during your stay.

Windham is situated near several scenic lakes, offering opportunities for outdoor activities such as hiking, fishing, and kayaking, which can provide a refreshing break from work. The town also boasts charming local shops and dining options, allowing you to easily explore the community during your downtime. 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 cater to a variety of traveler needs, with many properties featuring essential conveniences such as kitchens, which allow guests to prepare their own meals and enjoy home-cooked dining. Outdoor spaces are also common, with decks or patios providing a ideal setting for relaxation and enjoying the serene surroundings. Travelers can expect additional amenities like blenders for smoothies or mixed drinks, onsite parking for convenience, and coffee or tea makers to start the day with a warm beverage.
When is the best time to visit Windham for a vacation rental?
The best time to book a vacation rental in Windham is during the summer months, particularly in July. This peak season, spanning from June to August, draws travelers eager to enjoy the warm weather and partake in a variety of outdoor activities. With average temperatures ranging from the mid-60s to the low 80s Fahrenheit, it's an ideal time to explore the stunning landscapes and engage in activities like hiking, kayaking, and fishing in the nearby lakes.

July, specifically, brings a vibrant setting as families and adventure seekers flock to the area. Visitors can revel in the long, sunny days, making it great for sightseeing in the picturesque surroundings. The laid-back charm of Windham, combined with its access to nature, makes it a fantastic destination for those looking to unwind and enjoy quality time outdoors.

For those seeking a more budget-friendly option, consider visiting in November. Although it's quieter, this month offers a unique charm with fall remnants and the start of early winter activities. You can enjoy peaceful walks and perhaps some early seasonal festivities, all while avoiding the hustle and bustle of peak tourist crowds.
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, Maine, United States of America?
In Windham, Maine, visitors can enjoy a variety of attractions that highlight the area's natural beauty and recreational opportunities. The Sebago Lake region is a major draw, offering activities such as boating, fishing, and swimming during the warmer months. Many vacation rentals are situated near the lake, providing easy access to its pristine shores and scenic views.

The nearby Windham Town Center features local shops, restaurants, and cafes, making it a great spot for dining and shopping. For outdoor enthusiasts, the surrounding areas offer hiking trails and parks, such as the picturesque Black Brook Preserve, which is superb for exploring nature and enjoying peaceful walks.

Additionally, Windham is conveniently located near the larger city of Portland, allowing visitors to experience more urban attractions, including art galleries, museums, and the vibrant waterfront.
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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