Windham holiday lettings

We found 1,214 holiday rentals — enter your dates for availability

Select from 32 homes, 12 cottages and other holiday rentals in Windham to find one that's perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as a garden and pool. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Windham

Showing deals for:28 Nov - 5 Dec

Image gallery for Spacious country house near lakes and skiing, convenient to downtown Bridgton.

View from the kitchen window. Large yard with room to park cars, RV/boat.
9.8 out of 10 rating
Exceptional
(17 reviews)

Spacious country house near lakes and skiing, convenient to downtown Bridgton.

Bridgton, ME

12% off
Price is £2,063
for 7 nights, 1 home
£295 nightly
Includes taxes & fees
Spacious country house near lakes and skiing, convenient to downtown Bridgton.

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Find out more about Windham

Find out more about Windham

Travel to friendly Windham

The lake and other outdoor surroundings create an inviting atmosphere in Windham. This welcoming city attracts visitors thanks to its restaurants and shopping. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Windham

Are you searching for attractions to see in the city? Venture out of your holiday home and experience everything that makes Windham a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Windham. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport to and around Windham

The nearest airport is in Portland, ME (PWM-Portland Intl. Jetport), located 8.9 mi (14.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly 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 holiday rental?
When considering a holiday rental in Windham, Maine, a popular area to stay is the vicinity of Jordan Bay. This picturesque neighbourhood boasts stunning waterfront views and offers a serene atmosphere, great for a relaxing getaway. The proximity to the bay allows for various outdoor activities, including kayaking and fishing, making it a favourite among nature enthusiasts.

Another appealing area is the Windham Centre, which is conveniently located near many local amenities. Here, you'll find charming shops and eateries that reflect the character of the community. Additionally, Windham Centre is close to the great Sebago Lake State Park, a fantastic spot for hiking and enjoying the outdoors.

If you prefer a more rural setting, the areas surrounding the Pleasant River are also worth considering. This tranquil region is ideal for those looking to escape the hustle and bustle, with numerous properties available that offer a rustic charm and easy access to scenic trails.
How much does it cost to rent a holiday home in Windham?
Prices for holiday 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 holiday 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 Windham ski resort rentals?
For ski resort rentals in Windham, Maine, travellers should focus on the area surrounding Windham Mountain, which is renowned for its winter sports offerings. The immediate vicinity offers a range of accommodation options, including modern lodges and quaint cabins that cater to different group sizes. Many of these properties are equipped with essential amenities such as full kitchens, cosy living areas, and often feature fireplaces, great for unwinding after a day on the slopes.

In addition to the mountain accommodations, the nearby town of Windham provides a variety of rental options, from charming chalets to larger homes suitable for families or groups. These properties typically come with conveniences like laundry facilities, Wi-Fi, and sometimes outdoor spaces for enjoying the scenic views. Moreover, being close to local shops and eateries enhances the overall experience, allowing guests to easily access dining and shopping opportunities.
What is the most popular type of holiday rental accomodation in Windham?
In Windham, holiday houses are the most popular type of rental, with around 27 available throughout the area. These properties typically offer spacious interiors with multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. Many holiday houses are situated in serene neighbourhoods, providing a superb backdrop for enjoying the natural beauty of the region, including proximity to local lakes and hiking trails.
Are there any family house rentals in Windham?
In Windham, Maine, there are numerous family-friendly house rentals available, with around 29 options to choose from. The area is well-suited for families, offering spacious rooms that often include multiple bedrooms, fully equipped kitchens, and outdoor areas great for children to enjoy. Many properties also feature amenities like Wi-Fi, laundry facilities, and sometimes even game rooms or outdoor fire pits for evening gatherings.
Can I rent a holiday home with a pool or hot tub in Windham?
In Windham, Maine, there are several holiday homes available for rent that feature pools and hot tubs, suiting those seeking a relaxing getaway. The area is known for its picturesque landscapes and proximity to the Sebago Lakes region, making it an appealing destination for outdoor enthusiasts. Many properties come equipped with amenities such as private pools, hot tubs, spacious outdoor decks, and fully stocked kitchens, ideal for both leisure and family gatherings. Additionally, some rentals may offer waterfront access, allowing guests to enjoy activities such as swimming or kayaking right from their doorstep.
Can I find long-stay holiday rentals in Windham?
A long-stay holiday rental in Windham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Windham?
In Windham, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come with amenities such as spacious backyards, modern kitchens, and comfortable living areas, making them suitable for families and groups.
Are there any remote work holiday rentals in Windham?
In Windham, Maine, there is a wide selection of remote work holiday rentals available, with around 41 options to choose from. This charming area is not only known for its scenic beauty but also offers a conducive environment for those looking to work remotely. Many properties come equipped with essential amenities such as Wi-Fi, dedicated office spaces, and comfortable desks and chairs, ensuring that professionals can maintain productivity during their stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windham holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Windham with parking available—perfect for families or travellers 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 holiday rentals typically feature a range of amenities that enhance the comfort of guests. Most properties come equipped with a kitchen, allowing travellers to prepare their own meals, along with essential cookware, dishware, and utensils. Free Wi-Fi is commonly available, ensuring that guests can stay connected during their stay. Additionally, many rentals include a microwave for convenience, making it easy to heat up leftovers or prepare quick snacks.
When is the best time to visit Windham for a holiday rental?
The best time to visit Windham for a holiday rental is during the summer months, particularly in July, when the area comes alive with vibrant outdoor activities and warm weather. This peak season, running from June to August, is ideal for those looking to embrace the great outdoors. Visitors can enjoy hiking, boating, and exploring the stunning lakes that Windham has to offer, all under the clear blue skies and pleasant temperatures typically reaching the mid to high 20s Celsius.

July is especially popular, as families flock to the region for its numerous summer festivals and events, allowing for socialising and creating memorable experiences. The atmosphere is energetic, with plenty of opportunities for water sports and picnicking by the lakeside.

For those seeking a quieter experience with significant savings, November is an excellent choice. During this low season, the landscape transforms with autumn colours, providing a picturesque backdrop for peaceful walks and reflections. Crisp air and the absence of crowds allow for a more intimate exploration of Windham's natural beauty.
How early should I book a Windham holiday rental?
Book your Windham holiday 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 holiday 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 variety of attractions that showcase the beauty of the area. The picturesque Sebago Lake is a major draw, offering opportunities for swimming, boating, and fishing, with several holiday rentals providing easy access to its shores. The nearby Windham Town Common features lovely walking paths and hosts community events throughout the year.
Can I change or cancel my Windham home rental booking on Vrbo?
To find Windham holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Windham holiday 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.

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