Windham holiday rentals

We found 1,287 holiday rentals — enter your dates for availability
Select from 37 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:18 Dec - 25 Dec

Terrace/patio
Living area
Exterior
Private kitchen
Exceptional
(21 reviews)

Luxury Log Cabin • Paradise in the Lakes Region

Naples

8% off
AU$6,522
for 7 nights, 1 home
AU$932 per night
includes taxes & fees
Luxury Log Cabin • Paradise in the Lakes Region
Private kitchen
Living area
Interior
Exterior
Exceptional
(21 reviews)

Entire House - three suites - conferences, reunions, retreats

Westbrook

8% off
AU$10,974
for 7 nights, 1 home
AU$1,568 per night
includes taxes & fees
Entire House - three suites - conferences, reunions, retreats
Side garden
Patio
Downtown Naples along the Causeway
Main floor living room
Exceptional
(49 reviews)

Luxury English Country Home

Naples

8% off
AU$6,918
for 7 nights, 1 home
AU$988 per night
includes taxes & fees
Luxury English Country Home
Property grounds
Living area
Exterior
Dining
Exceptional
(11 reviews)

Luxury Lakefront home on Sebago Lake W/ Sandy Beach

Raymond

8% off
AU$7,908
for 7 nights, 1 home
AU$1,130 per night
includes taxes & fees
Luxury Lakefront home on Sebago Lake W/ Sandy Beach
Outdoor dining
Private kitchen
Living area
Private sandy beach area
Wonderful
(5 reviews)

Lakefront 15 mins from Portland with Private Beach and Fenced in Yard

Windham

21% off
AU$7,063
for 7 nights, 1 home
AU$1,009 per night
includes taxes & fees
Lakefront 15 mins from Portland with Private Beach and Fenced in Yard
... or work on the kitchen island.
The newly renovated lakeside deck is the hub of activity Spring, Summer & Fall.
The newly renovated living room overlooks the porch room, deck and lake.
Check out this view of the house at dusk in March ... such tranquility.
Exceptional
(77 reviews)

Tranquil, Serene Sebago Lakefront House on 2 Wooded Acres - 300ft Waterfront!

Casco

8% off
AU$8,511
for 7 nights, 1 home
AU$1,216 per night
includes taxes & fees
Tranquil, Serene Sebago Lakefront House on 2 Wooded Acres - 300ft Waterfront!
Visit for the holidays!
Library to read a book with a cool breeze from the water!
View of the river that leads into Sebago Lake.
View from 2nd floor deck
Exceptional
(162 reviews)

Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!

Naples

8% off
AU$1,507
for 7 nights, 1 cottage
AU$215 per night
includes taxes & fees
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Interior
Terrace/patio
Interior
Interior
Exceptional
(9 reviews)

LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

Naples

8% off
AU$7,023
for 7 nights, 1 home
AU$1,003 per night
includes taxes & fees
LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
Back door porch leads to the firepit and water.
Rent a boat during your stay. Many marinas in the area.
Firepit photo taken from the riverbank, free use of the canoe
Cool breeze from the river!
Exceptional
(130 reviews)

Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

Naples

8% off
AU$1,536
for 7 nights, 1 cottage
AU$219 per night
includes taxes & fees
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
Master bedroom with queen bed and ceiling fan
Willard Beach
Back yard
Living area
Exceptional
(72 reviews)

Willard Beach Neighborhood-Close to all Southern Maine has to offer!

South Portland

8% off
AU$4,375
for 7 nights, 1 home
AU$625 per night
includes taxes & fees
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
Exterior
Gas firepit installed May 2026.
Dining Room with cherry table, seating for 8 people. View of back yard & deck.
Swimming area at Trickey Pond. 2 single kayaks and life jackets are provided.
Exceptional
(31 reviews)

Spacious Trickey Moose Family Retreat - Woodstove, Firepit, Kayaks, Water Access

Naples

8% off
AU$4,487
for 7 nights, 1 home
AU$641 per night
includes taxes & fees
Spacious Trickey Moose Family Retreat - Woodstove, Firepit, Kayaks, Water Access
Outdoor dining
Private kitchen
Living area
Interior
Exceptional
(15 reviews)

House at Sunshine- Long Lake, 5 min walk to causeway

Naples

8% off
AU$3,539
for 7 nights, 1 home
AU$506 per night
includes taxes & fees
House at Sunshine- Long Lake, 5 min walk to causeway
Interior
Property grounds
Interior
Private kitchen
Exceptional
(10 reviews)

Peaceful Lakeside Oasis Near City Amenities

Windham

8% off
AU$3,572
for 7 nights, 1 home
AU$510 per night
includes taxes & fees
Peaceful Lakeside Oasis Near City Amenities
The living room leads out to a private deck with a dining table that seats 4.
Outdoor dining
Exterior detail
Private kitchen
Exceptional
(43 reviews)

Modern & Sunny House Steps from the Promenade.

Portland

8% off
AU$3,913
for 7 nights, 1 home
AU$559 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade.
Kitchen
Casco Bay
Dining area
WELCOME
Exceptional
(101 reviews)

Beautiful Oceanfront Apartment, scenic views and water access

Yarmouth

8% off
AU$2,919
for 7 nights, 1 apartment
AU$417 per night
includes taxes & fees
Beautiful Oceanfront Apartment, scenic views and water access
Exterior
Outdoor dining
Living room
View from the kitchen window. Large yard with room to park cars, RV/boat.
Exceptional
(21 reviews)

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

Bridgton

12% off
AU$3,362
for 7 nights, 1 home
AU$480 per night
includes taxes & fees
Spacious country house near lakes and skiing, convenient to downtown Bridgton.
Property grounds
Private kitchen
Interior
Exterior
Exceptional
(24 reviews)

Modern Mountain Home- Family Friendly Close to Moose Pond / Pleasant Mountain

Bridgton

12% off
AU$2,922
for 7 nights, 1 home
AU$417 per night
includes taxes & fees
Modern Mountain Home- Family Friendly Close to Moose Pond / Pleasant Mountain
Closest sandy beach at the nearby Woods Pond with the playground for 2-12 y/o
New in 2024: solar lights to complement the cozy experience our fire pit offers.
Quiescent town of Bridgton, ME. Only13 minutes drive from Vacationland Retreat.
Blooming rockery in the back yard.
Exceptional
(33 reviews)

Vacationland Retreat Lake House w/private dock near Pleasant Mnt Cranmore Sebago

Denmark

8% off
AU$2,498
for 7 nights, 1 home
AU$357 per night
includes taxes & fees
Vacationland Retreat Lake House w/private dock near Pleasant Mnt Cranmore Sebago
Private kitchen
Marina
Living area
Dining
Exceptional
(13 reviews)

Renovated Apartment in Willard Square Area of South Portland, Maine.

South Portland

16% off
AU$2,547
for 7 nights, 1 apartment
AU$364 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
Dining
Living area
Interior
Private kitchen
Exceptional
(134 reviews)

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Portland

12% off
AU$2,935
for 7 nights, 1 apartment
AU$419 per night
includes taxes & fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
Large open concept living space with tall sloped celling and a loft.
View from inside unit.
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Exceptional
(7 reviews)

Exchange Street Skylight Loft

Portland

8% off
AU$3,888
for 7 nights, 1 apartment
AU$555 per night
includes taxes & fees
Exchange Street Skylight Loft
Space for shoes and coats before going upstairs into the living space.
Walk around behind the garage to access the apartment.
Room
Your private deck and entrance.
Exceptional
(16 reviews)

Private studio nestled in woods outside Portland

Westbrook

13% off
AU$2,172
for 7 nights, 1 apartment
AU$310 per night
includes taxes & fees
Private studio nestled in woods outside Portland
Dining
Outdoor dining
Living area
Interior
Exceptional
(13 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
AU$2,197
for 7 nights, 1 apartment
AU$314 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Interior
Living area
Off-street parking behind building dedicated to this unit only.
Room
Exceptional
(41 reviews)

Eastbayside/Munjoy - Charming Downtown Escape

Portland

8% off
AU$2,681
for 7 nights, 1 apartment
AU$383 per night
includes taxes & fees
Eastbayside/Munjoy - Charming Downtown Escape

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Riverside Municipal Golf Course (5.4 mi / 8.7 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 near the village centre. This charming neighbourhood offers a blend of convenience and local character, making it a great base for your holiday. You'll find a variety of properties available, ranging from quaint cottages to larger family homes, suiting different tastes and budgets.Staying in the village centre puts you in close proximity to some delightful attractions. For instance, you can enjoy the scenic beauty of Sebago Lake, which is great for swimming, boating, and picnicking during the warmer months. Additionally, the nearby Windham Town Common is a lovely spot for leisurely strolls or community events, often providing a taste of local culture and activities.Another appealing option is the area around the lakes, which offers a more tranquil setting for those wanting to unwind. Here, you can find properties with picturesque views and easy access to nature trails. The natural surroundings enhance the experience, allowing you to immerse yourself in the stunning landscapes that define this part of Maine.
Where are the best areas for renting a beach house in Windham?
For renting a beach house in Windham, Maine, the picturesque area around Sebago Lake is a prime choice. This region is known for its beautiful sandy beaches and clear waters, making it ideal for summer getaways. Properties here often feature spacious decks with lake views, outdoor grilling areas, and private docks for boating or swimming. Many rentals come with amenities such as full kitchens, multiple bedrooms, and access to kayaks or paddleboards, suiting families and groups seeking a relaxing lakeside experience.Additionally, the nearby town of Naples offers charming waterfront cottages and homes, allowing easy access to both the lake and local dining options. Visitors can enjoy amenities like fire pits for evening gatherings and spacious living areas great for socialising after a day of outdoor activities. The proximity to the Sebago Lake State Park further enhances the appeal, providing opportunities for hiking, picnicking, and exploring nature trails.
Where are the best Windham ski resort rentals?
For the best rentals near Windham ski resort, travellers should consider options in the nearby town of Windham itself. This charming town offers a variety of accommodations, from cosy cabins to larger holiday homes, many of which provide convenient amenities for guests. Properties often feature fully equipped kitchens, spacious living areas with fireplaces, and outdoor decks superb for enjoying the scenic views of the surrounding mountains.Additionally, rentals in the vicinity typically come with easy access to the ski resort, allowing guests to hit the slopes with minimal hassle. Many homes offer amenities like ski storage and laundry facilities, suiting the needs of winter sports enthusiasts.For those interested in exploring beyond skiing, the region also boasts beautiful hiking trails and local attractions, including quaint shops and restaurants that highlight the area's charm.
What is the most popular type of holiday rental accomodation in Windham?
In Windham, holiday houses are the most popular type of holiday rental, with about 87 available throughout the area. These properties typically offer spacious living areas, fully equipped kitchens, and multiple bedrooms, making them ideal for families or larger groups. Many holiday houses also feature outdoor spaces such as decks or patios, great for enjoying the beautiful surroundings. Additionally, there are around 30 cottages and a dozen cabins, which provide a more rustic charm and are often set in tranquil locations. For those seeking a more compact option, several apartments and villas are also available, suiting a variety of tastes and preferences.
Are there any family house rentals in Windham?
In Windham, Maine, there is a good selection of family-friendly house rentals, with around 32 properties available for visitors. The area is known for its beautiful natural surroundings and outdoor activities, making it an excellent choice for families seeking adventure. Many of these homes offer spacious living areas, fully equipped kitchens superb for preparing family meals, and outdoor spaces where children can play or enjoy barbecues.The locale is close to several attractions, including the picturesque Sebago Lake, where families can partake in swimming, fishing, and boating during the warmer months. Additionally, nearby Windham Town Beach provides a lovely spot for relaxation and picnics. With amenities such as Wi-Fi, air conditioning, and sometimes even game rooms or fire pits, these accommodations provide a comfortable base for exploring the scenic beauty of the region.
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 or hot tubs. This charming town, located near the picturesque Sebago Lake, offers a range of options for those looking to enjoy a relaxing getaway. Many of these properties come equipped with private pools or hot tubs, great for unwinding after a day of exploring the local area.Travellers can expect a variety of amenities, including spacious outdoor areas, fully equipped kitchens, and comfortable living spaces designed for family gatherings or group retreats. The serene surroundings provide a tranquil backdrop, while the nearby lake and parks offer opportunities for outdoor activities such as hiking, fishing, and swimming.
Are there pet-friendly house rentals in Windham?
In Windham, there are numerous pet-friendly house rentals available, with around 24 options to choose from, ensuring a variety of accommodations for travellers with pets. Many of these holiday homes come equipped with essential amenities such as full kitchens, comfortable living spaces, and often outdoor areas where pets can roam freely. Some rentals may even feature fenced yards, making them particularly suitable for pet owners.The area boasts beautiful outdoor surroundings, with opportunities for hiking and exploring nature, which can be delightful for both you and your furry companions. Nearby local parks provide additional spaces for walks and play, enhancing the overall experience for pet owners.
Are there any remote work holiday rentals in Windham?
In Windham, Maine, there are numerous remote work-friendly holiday rentals available, with around 126 options to choose from. Many of these properties are equipped with essential amenities for working remotely, such as free Wi-Fi, dedicated desks, and comfortable desk chairs, ensuring a productive environment. Some rentals even feature computer monitors, making it easy to set up a home office while enjoying the beauty of the area.Travellers can expect a variety of accommodations, including spacious homes and cosy cabins that offer both comfort and functionality. The town is conveniently located near stunning natural landscapes, including lakes and hiking trails, providing an ideal backdrop for breaks from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Windham?
In Windham, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor space to relax and enjoy the fresh air. Additional conveniences often found in these rentals include blenders for making smoothies or other refreshments, onsite parking for easy access, and coffee and tea makers to ensure that guests can enjoy their favourite hot beverages at any time.
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 peak season from June to August, with July being particularly popular among travellers seeking outdoor adventures. This vibrant period invites visitors to indulge in a variety of activities, from hiking and kayaking to enjoying local festivals that celebrate the charm of this picturesque Maine town.The summer months bring warm temperatures, typically ranging from 15 to 30 degrees Celsius, creating ideal conditions for outdoor exploration. The lush scenery and numerous lakes provide a stunning backdrop for sightseeing and recreational activities, ensuring that you can comfortably embrace the beauty of nature and engage in fun-filled adventures.If you're looking for a more budget-friendly option, consider visiting in November. While this month is quieter, it offers a unique opportunity to experience the serene beauty of Windham as the fall foliage transforms the landscape into a canvas of warm colours. This is a fantastic time for peaceful walks and enjoying the local atmosphere without the hustle and bustle of the peak season.Ultimately, your choice of when to visit Windham will depend on whether you prefer the lively summer atmosphere filled with activities or the tranquil charm of autumn.
What are the top attractions in Windham?
In Windham, Maine, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. One of the main draws is Sebago Lake, which offers opportunities for swimming, boating, and fishing. The surrounding parks, such as Sebago Lake State Park, provide scenic picnic spots and hiking trails for those looking to explore the local landscape.For families, the nearby Windham Mall features various shops and dining options, making it a convenient stop for visitors. The town also has a vibrant community with seasonal events and festivals, particularly during the summer months, offering a taste of local culture.
Are all fees included in the Windham holiday homes prices shown on Stayz?
Stayz 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.
Are there any Windham holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Windham holiday homes?
You can find great discounts on holiday homes in Windham on Stayz, 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.
Can I change or cancel my Windham holiday home booking on Stayz?
To find Windham holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Windham?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Windham holiday home?
Book your Windham holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windham?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Windham to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.