Best Vacation Homes in Windham
House
10.0(58 Reviews)
2 Bedrooms
2 Baths
6 Guests
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $401/Night
7 Nights - US $2,810
House
2 Bedrooms
1 Bath
6 Guests
699.65 ft²
- Balcony/Terrace
Pet Friendly
Kitchen
Parking
US $391/Night
7 Nights - US $2,737
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Air Conditioner
US $440/Night
7 Nights - US $3,083
House
2 Bedrooms
1 Bath
6 Guests
699.65 ft²
Skiing- Fireplace/Heating
Breakfast- Pet Friendly
US $312/Night
7 Nights - US $2,184
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $306/Night
7 Nights - US $2,140
Cottage
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
Internet
US $187/Night
7 Nights - US $1,308
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $339/Night
7 Nights - US $2,372
Windham Luxury Rentals
House
10.0(22 Reviews)
6 Bedrooms
5 Baths
15 Guests
Hot Tub- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,319/Night
7 Nights - US $9,234
New
House
10.0(1 Review)
5 Bedrooms
3 Baths
12 Guests
2400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,261/Night
7 Nights - US $8,829
Cottage
10.0(5 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $1,181/Night
7 Nights - US $8,265
House
10.0(75 Reviews)
5 Bedrooms
3 Baths
16 Guests
3300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,088/Night
7 Nights - US $7,619
House
6 Bedrooms
2 Baths
12 Guests
2500 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,085/Night
7 Nights - US $7,595
House
9.8(26 Reviews)
5 Bedrooms
3 Baths
12 Guests
3500 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,059/Night
7 Nights - US $7,416
House
9.8(9 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
US $1,020/Night
7 Nights - US $7,141
House
10.0(63 Reviews)
4 Bedrooms
2 Baths
9 Guests
3300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $953/Night
7 Nights - US $6,669
Windham Pet Friendly Vacation Rentals
Cottage
9.6(8 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $313/Night
7 Nights - US $2,190
House
6 Bedrooms
2 Baths
12 Guests
2497.23 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $670/Night
7 Nights - US $4,691
Cottage
8.8(43 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $361/Night
7 Nights - US $2,529
Villa
2 Bedrooms
1 Bath
5 Guests
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $229/Night
7 Nights - US $1,601
Cabin
8.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $405/Night
7 Nights - US $2,838
House
10.0(35 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $390/Night
7 Nights - US $2,728
Cabin
10.0(25 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $516/Night
7 Nights - US $3,613
House
10.0(13 Reviews)
4 Bedrooms
2 Baths
10 Guests
Private Pool- Hot Tub
- Fireplace/Heating
Pool
US $815/Night
7 Nights - US $5,703
Windham Large Vacation Homes
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
11 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $645/Night
7 Nights - US $4,516
House
9.8(41 Reviews)
5 Bedrooms
2 Baths
10 Guests
2200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $534/Night
7 Nights - US $3,739
House
9.8(32 Reviews)
5 Bedrooms
2 Baths
14 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $660/Night
7 Nights - US $4,622
House
9.6(11 Reviews)
5 Bedrooms
2 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $640/Night
7 Nights - US $4,483
House
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $529/Night
7 Nights - US $3,701
House
10.0(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $886/Night
7 Nights - US $6,203
Cottage
10.0(4 Reviews)
6 Bedrooms
1 Bath
11 Guests
1519 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $409/Night
7 Nights - US $2,861
House
10.0(1 Review)
4 Bedrooms
1 Bath
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $709/Night
7 Nights - US $4,962
Why Choose Rent By Owner for your Windham Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windham
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this charming area ensures you can experience its natural beauty and local activities at their best, making your stay in Windham, Maine, USA, truly memorable and aligning perfectly with your vacation plans.
Peak Season Highlights
Summer (June to August)
During the warmest months, the area experiences peak travel as visitors seek outdoor activities and scenic views. This is ideal for enjoying the natural beauty and recreational opportunities that this destination offers.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn draws travelers who want to witness the vibrant foliage and cooler weather. It’s a popular time for exploring local landscapes and enjoying seasonal festivities in the region.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
This quieter period offers fewer crowds, making it perfect for those seeking tranquility and cozy accommodations. The cold weather creates a peaceful atmosphere for relaxing indoors or enjoying winter sports nearby.
Average Temperature Daytime: 25°F to 35°F - Nighttime: 15°F to 25°F
Spring (March to May)
As the season transitions, fewer visitors come to enjoy the emerging warmth and blooming scenery. It’s an excellent time for affordable stays and discovering the area's early spring charm.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Windham
How to Book Your Windham Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windham
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor grilling with a private barbecue area to savor meals amidst scenic surroundings.
- Relax in a spacious backyard or garden perfect for outdoor gatherings and family activities.
- Make the most of a shared or private swimming pool during warm summer days.
- Take advantage of nearby hiking trails and nature paths for exploring the picturesque landscape.
- Benefit from on-site parking facilities that provide easy access to your adventures in the region.
- Utilize outdoor fire pits or fireplaces ideal for cozy evenings under the stars.
- Access to outdoor recreational equipment such as bikes, kayaks, or paddleboards to enhance your stay here.
Top Attractions Around Windham
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities such as hiking, fishing, and exploring scenic trails just moments from your vacation rental in Windham, Maine.
Family Activities
- Windham Pond Park: Enjoy a family picnic and leisurely strolls along the scenic trails in a peaceful natural setting that’s perfect for outdoor fun.
- Seacoast Adventure Mini Golf: Challenge each other to a friendly game on the colorful course, providing entertainment for all ages within easy reach of your vacation rental.
- Funtown Splashtown USA: Make a splash at this popular amusement park featuring water rides and thrill attractions, ideal for a day filled with excitement for the whole family.
- Windham Historical Society Museum: Explore local history through engaging exhibits that offer educational experiences while fostering curiosity about the region’s heritage.
Adult Activities
- Hiking and Nature Trails: Explore the scenic trails within the region that offer stunning views and a peaceful escape into nature.
- Fishing at Local Lakes and Rivers: Enjoy a relaxing day casting your line in the nearby lakes and rivers, renowned for their abundant freshwater fishing opportunities.
- Golf Courses and Leisure Sports: Play a round on well-maintained golf courses that provide a perfect setting for both beginners and experienced players.
- Visit Local Breweries and Distilleries: Indulge in tasting sessions at the area's craft breweries and distilleries, showcasing the region's vibrant beverage scene.
Other Places to Stay in Windham, ME
Seacoast Adventure
Sebago Lake Basin
Little Falls-South Windham
North Windham
Mercy Primary Care
Maine Wildlife Park
Windham Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the region's natural beauty by engaging in hiking, biking, or kayaking to fully experience the area’s scenic landscapes.
- Plan your visit around seasonal events: Check the calendar for seasonal festivals or community gatherings that can enrich your stay here with authentic local culture.
- Choose a centrally located rental: Opt for a vacation rental close to key amenities and attractions to maximize your leisure time without unnecessary travel.
- Discover local dining options: Savor regional flavors by exploring nearby restaurants and markets, adding an authentic touch to your stay in the area.
Transportation Options
- Windham Transportation Services: Local shuttle and taxi options are available for convenient travel around the area and to nearby attractions.
- Public Transit: The region is serviced by regional bus networks that connect you to Portland and other key destinations in southern Maine.
- Rental Car Companies: Several rental agencies operate nearby, giving you flexible transportation options for exploring the surroundings at your own pace.
- Bike Rentals and Trails: Biking is a popular way to experience the area's scenic beauty, with bike rentals readily available and dedicated trails for leisurely rides.
Local Customs Options
- Lobster Boil Traditions: Participating in a traditional Maine lobster boil is a local custom that reflects the region’s rich maritime heritage, often enjoyed during gatherings here.
- Seaside Festivals: Attending seasonal festivals along the coast celebrates local culture and community spirit, making it a memorable experience during your stay.
- Farmers' Market Visits: Visiting farmers' markets showcases the area's fresh, locally sourced produce and supports sustainable local agriculture.
- Historical Preservation: Respecting the preservation of historic sites and architecture highlights the community’s appreciation for its history and traditions.
Windham Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Windham?
There are a lot of options in Windham. If you plan on staying in the Windham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windham:
- Sunny Waterfront Family Friendly Little Sebago Home
- SEBAGO LAKE HOME WITH 2 WALK OUT SANDY ASSOC BEACH
- Steps from the beach on Sebago Lake Basin
- Lakefront House
- Family & dog friendly historic 4BR farmhouse near Sebago Lake w/boat launch!
- Cozy 100-year-old Maine camp, steps to Little Sebago Lake
- Rise & Shine - Breathtaking Sebago Lake view
- Nature, Pool, Hot tub&Lakes! Mins to Sebago &More
- Rosebud on Little Sebago Lake
- Brand New Lake Home with Great Sandy beach on Sebago’s Basin
2. Which vacation homes in Windham are best for families?
If you are looking for a family-friendly vacation home in Windham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windham:
3. How many Rentbyowner vacation rentals are available in Windham?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 108 in the Windham area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windham.
4. What is the cancellation policy for vacation rentals in this area?
The cancellation policy varies by listing, so it's important to review the specific terms outlined in each property’s description before booking. For detailed information, contact the property owner directly.
5. Are there any specific house rules I should be aware of when staying in a vacation rental in this destination?
Yes, each property has its own house rules listed in the rental details. Be sure to read these carefully before confirming your reservation to ensure a smooth stay.
6. How do I know if a vacation rental in this region is available for my travel dates?
Availability can be checked directly through the listing by selecting your preferred dates. If you have questions about availability or need assistance, reaching out to the property owner is recommended.
7. What amenities are typically included in vacation rentals here?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, heating or air conditioning, and outdoor spaces. To confirm, review each listing’s amenities section or contact the owner directly.
8. Is there a secure process for paying and confirming my booking in this area?
Yes, bookings are processed through a secure platform that ensures your payment information is protected. Once your reservation is confirmed, you'll receive all necessary details from the property owner to prepare for your stay.
Windham Top Rated Vacation Rentals
House
10.0(29 Reviews)
4 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $429/Night
7 Nights - US $3,004
Apartment
5.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
Spa- Fireplace/Heating
- Pool
Lake View
US $324/Night
7 Nights - US $2,270
