Windham, Maine Vacation Rentals

Explore 76 rental homes and villas in Windham, Maine for your next vacation or business travel. With private vacation home rentals, enjoy a more personalized stay and a wide range of amenities such as Air Condition Homes, Best Affordable Homes and Great for Groups. With a wide range of homes to offer, pricing can start as low as $84 per night with homes containing as many as 8 bedrooms and 6 bathrooms. However you're looking to experience your stay, Homes and Villas by Marriott has your next vacation home waiting.

Types of vacation rentals in Windham

Where to stay in Windham

Show all homes

Booking a vacation rental in Windham, Maine?

Here are some things to know to support your visit:

Windham Overview
Windham, Maine, is a hidden gem nestled in the heart of New England, offering a tranquil retreat with the quintessential charm of the region. As a part of the picturesque Lakes Region of Southern Maine, Windham is not just a destination; it's an experience that invites you to immerse yourself in the natural beauty and serenity of the area. Imagine waking up in your own private home, surrounded by the lush landscapes of Windham, with the freedom to plan your day at your own pace. Rental homes here are not only abundant but come with a variety of amenities to enhance your stay. Many of these homes are pet-friendly, allowing you to bring your furry friends along for the adventure. For those warm summer days, select a home with a swimming pool to add a touch of luxury and relaxation to your getaway. The crown jewel of Windham is undoubtedly Sebago Lake, Maine's second-largest lake, known for its crystal-clear waters that beckon visitors to dive into a range of water activities. Boating, fishing, and swimming are just the beginning of what you can enjoy on this expansive body of water. Imagine renting a home with direct waterfront access, where the gentle lapping of the waves against the shore provides the perfect soundtrack to your stay. Sebago Lake State Park is a must-visit, offering a plethora of outdoor activities. Hike through verdant forests, enjoy a family picnic with the lake as your backdrop, or simply bask in the sun on the park's sandy beaches. Anglers will delight in the opportunity to catch landlocked salmon and trout, while adrenaline seekers can take to the lake for sailing and waterskiing adventures. Though Windham exudes small-town tranquility, it's conveniently located a short drive from Portland, allowing for easy exploration of urban attractions. Within Windham itself, you'll discover charming local shops, inviting restaurants, and community events that reflect the town's warm hospitality. The Windham Historical Society is a treasure trove for those interested in the local lore, offering insights into the town's rich heritage through engaging exhibits and events. As the seasons change, Windham reveals its ever-shifting beauty. Autumn cloaks the landscape in a tapestry of fiery hues, perfect for scenic drives and photography. Come winter, the area transforms into a snowy playground, with cross-country skiing and snowshoeing trails, and nearby ski resorts like Shawnee Peak and Sunday River offering slopes for all levels. Local festivals and fairs throughout the year showcase Windham's vibrant community spirit, featuring live music, crafts, and delectable Maine fare. Windham, Maine, is a destination that truly caters to every preference, whether you're in search of outdoor thrills, a peaceful escape, or a cozy nook to relax and reconnect with nature. Here, you'll find a slice of New England paradise that feels like it's exclusively yours.
Cultural Attractions in Windham
Windham, Maine, may not be the first destination that comes to mind for a cultural enthusiast, but this charming town offers a tranquil setting for those looking to explore the arts, history, and local customs of New England. While Windham is a smaller community, it is within close proximity to Portland, Maine's cultural hub, which is just a short drive away. However, Windham itself has its own unique offerings. The Windham Historical Society provides a glimpse into the area's past, with a collection of artifacts and exhibits that tell the story of the town's development from its early days to the present. For art lovers, the Sebago Lake region, of which Windham is a part, hosts local artists and craftsmen whose works reflect the natural beauty of Maine. Galleries in the area showcase paintings, sculptures, and crafts that are inspired by the state's landscapes and seasons. The nearby town of Gorham often has art events and exhibitions at the University of Southern Maine Art Gallery, which features contemporary works by regional artists. Live music can be found at local venues and seasonal festivals. The Windham Summerfest is an annual event that celebrates the community with music, food, and entertainment. Additionally, the nearby city of Portland offers a rich music scene with venues like the State Theatre and Port City Music Hall, where a variety of live performances can be enjoyed. For a more immersive experience in local customs, Windham's proximity to Portland allows for easy access to the city's First Friday Art Walk, where galleries and museums open their doors to the public for free. This monthly event is a fantastic way to engage with the local art community and experience the vibrant culture of the area. Windham's natural setting also provides a serene backdrop for those who appreciate the arts. The town is nestled among rolling hills and pristine lakes, offering inspiring vistas for plein air painting or photography. The local landscape is a canvas in itself, changing with the seasons and providing endless opportunities for artistic exploration. While Windham is a quieter destination, its New England charm and access to the cultural activities of the greater Portland area make it a delightful spot for those who enjoy the arts, history, and local customs. It's a place where one can enjoy the peacefulness of a small town while still being within reach of a lively cultural scene.
Kids IconFamily friendly activities in Windham
Windham, Maine, nestled in the scenic beauty of New England, offers a delightful array of activities that are sure to captivate children and provide a memorable family experience. Start your adventure at Seacoast Adventure, a fun park that offers a variety of attractions suitable for all ages. During the summer, kids can enjoy go-karts, mini-golf, and a sky swing, while winter brings the excitement of snow tubing. The park's Deck House Tavern provides a family-friendly dining option with a menu that caters to both adults and children. For those who love the great outdoors, Windham is a gateway to the Sebago Lake region. Spend a day at Sebago Lake State Park, where kids can splash in the water, build sandcastles on the beach, or explore the park's hiking trails. The clear, clean waters of the lake are perfect for a family swim or a leisurely boat ride. The Windham Historical Society offers a glimpse into the past with its Village Green, where families can explore historic buildings and learn about the area's heritage. Although it may be more appealing to older children with an interest in history, the picturesque setting makes it a pleasant stop for a family picnic. For a unique cinematic experience, take the family to the Pride's Corner Drive-In. This nostalgic outdoor movie theater allows you to watch the latest films under the stars, a special treat that combines entertainment with the charm of yesteryear. If your children are animal lovers, a visit to the Maine Wildlife Park in nearby Gray is a must. Here, they can see moose, bears, lynx, and other animals native to Maine. The park's interactive displays and educational programs make it both a fun and informative outing. For a more relaxed day, visit Tassel Top Park on the shores of Sebago Lake. With its sandy beach, snack shack, and nature trails, it's an ideal spot for families to unwind and enjoy Maine's natural beauty. Windham also offers a variety of dining options that are sure to please even the pickiest of eaters, from classic American fare to delicious ice cream at local parlors. In Windham, Maine, families can enjoy a blend of outdoor adventure, educational experiences, and simple pleasures, all set against the backdrop of New England's timeless charm. Whether you're seeking thrills at an adventure park or a peaceful day by the lake, Windham has something to offer for every child and those young at heart.
Nature IconOutdoor activities in Windham
Windham, Maine, nestled in the scenic beauty of New England, is a treasure trove of natural wonders and outdoor activities for those who seek to immerse themselves in nature. This charming town, located near the Sebago Lake region, offers a serene escape with its lush landscapes, waterways, and trails. Sebago Lake, Maine's second-largest lake, is a centerpiece of outdoor recreation in the area. It provides a perfect setting for boating, fishing, and swimming in its crystal-clear waters. The lake is known for its landlocked salmon and trout, making it a popular destination for anglers. Around the lake, visitors can find numerous spots for picnicking and enjoying the panoramic views. For hiking enthusiasts, the Mountain Division Trail offers a multi-use path that meanders through the picturesque Maine countryside. This trail is ideal for walking, biking, and even horseback riding, allowing visitors to take in the natural beauty at their own pace. The nearby Presumpscot River Preserve is another natural gem where outdoor lovers can connect with the environment. The preserve features trails that run alongside the river, providing opportunities for wildlife observation, photography, and the simple pleasure of a peaceful walk through the woods. Birdwatchers will find the Donnabeth Lippman Park a haven for local and migratory birds. The park's wetlands and forested areas are home to a variety of bird species, offering a tranquil spot for observation and listening to the melodic bird songs. For a more adventurous experience, the Windham area offers kayaking and canoeing opportunities on its many rivers and streams. Paddling through these waterways, one can discover secluded spots and enjoy the serenity of the Maine wilderness. In the winter months, Windham transforms into a snowy wonderland, with cross-country skiing and snowshoeing becoming popular activities. The landscape blanketed in white offers a different kind of beauty, and the crisp air invigorates the soul. Lastly, the nearby White Mountains of New Hampshire are just a short drive away, offering even more outdoor pursuits such as hiking, climbing, and skiing. The proximity to these majestic peaks adds another layer of allure for those staying in Windham. Windham, Maine, with its natural splendor and array of outdoor activities, is a destination that truly resonates with those who yearn to connect with nature. Whether it's on the water, in the forest, or amidst the mountains, Windham provides an idyllic backdrop for nature lovers to explore and enjoy.
Weather IconWeather in Windham
Windham, Maine, nestled in the picturesque New England region, experiences a four-season climate that offers a diverse range of weather conditions throughout the year, each with its own unique appeal. Winter, from December to February, is cold and snowy, with average temperatures ranging from 10°F to 31°F. Snowfall is significant, making Windham a winter wonderland, ideal for snow sports and cozy evenings by the fire. January is typically the coldest month, so visitors should come prepared with warm clothing and snow gear. Spring, from March to May, brings a gradual warming trend with temperatures ranging from 24°F to 65°F. This season can be unpredictable, with late snowfalls or early heatwaves. The melting snow and spring rains contribute to the lush greenery that emerges, making it a beautiful time for nature walks as the landscape reawakens. Summer, from June to August, is the warmest and most popular time to visit. Average temperatures range from 54°F to 80°F, with July being the hottest month. The humidity can be high, but it's also the season when Windham's lakes and outdoor activities are most enjoyable. Occasional thunderstorms are common, so it's wise to have a flexible itinerary. Autumn, from September to November, is a spectacular season in Windham, with the foliage turning vibrant shades of red, orange, and yellow. Temperatures cool down to a range of 36°F to 70°F, and the humidity drops, making it a perfect time for hiking and enjoying the fall scenery. This is also a popular season for visitors who come to witness the famous New England fall foliage. The most pleasant weather conditions are often found in late spring, when the temperatures are moderate and the landscape is blooming, and in early fall, when the humidity is lower and the autumn colors are at their peak. These times offer a balance of comfortable weather and the opportunity to experience Windham's natural beauty without the peak summer crowds. Regardless of the season, Windham's climate is part of its New England charm, offering visitors a chance to experience the quintessential seasonal changes that make this region so beloved. Whether you're looking to enjoy winter sports, summer lakes, spring blooms, or fall foliage, Windham provides a picturesque backdrop for a memorable visit.
Transportation in Windham
Windham, Maine, is a charming town nestled in the scenic Lakes Region of the state, offering a peaceful retreat with easy access to outdoor activities and local attractions. While it may not have the extensive transportation infrastructure of a major city, there are still several options for travelers to arrive, depart, and explore the area. Most visitors traveling to Windham will likely fly into the Portland International Jetport, which is approximately a 30-minute drive away. From the airport, renting a car is the most convenient option for reaching Windham and provides the flexibility to explore the surrounding region at your own pace. Ride-sharing services like Uber and Lyft, as well as local taxi companies, are also available for the journey from the airport to Windham. For those who prefer to travel by bus, there are regional bus services that connect Portland to Windham, although the schedules may be less frequent than in larger urban areas. Once in Windham, having a car is advantageous as public transportation options within the town are limited. Windham itself is not particularly walkable for a typical visitor, especially if you plan to visit various points of interest or enjoy the natural beauty of the area. The town is spread out, and many of the attractions, such as Sebago Lake, local parks, and hiking trails, are best accessed by car. However, the town center does have a selection of shops and restaurants that can be enjoyed on foot if you choose accommodations nearby. For those looking to explore the great outdoors, Windham offers easy access to the Sebago Lake region, where boating, fishing, and swimming are popular activities during the warmer months. In the winter, the nearby Shawnee Peak and other ski resorts provide opportunities for skiing and snowboarding. In summary, while Windham may not have the extensive public transportation systems of larger cities, it is well-serviced by road and is a short drive from Portland's airport. Renting a car is the most practical way to enjoy the freedom to explore Windham and the surrounding natural attractions at your leisure.