Windham Resorts
New
Cottage
2 Bedrooms
1 Bath
6 Guests
700 ft²
Fireplace/Heating
Pet Friendly
Kitchen
Parking
CA $463/Night
7 Nights - CA $3,240
House
9.3(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
699.65 ft²
Skiing- Fireplace/Heating
Breakfast- Pet Friendly
CA $441/Night
7 Nights - CA $3,088
CA $424/Night
7 Nights - CA $2,966
New
Cottage
2 Bedrooms
1 Bath
2 Guests
290 ft²
- Pet Friendly
- Kitchen
- Parking
Air Conditioner
CA $254/Night
7 Nights - CA $1,777
House
2 Bedrooms
1 Bath
6 Guests
699.65 ft²
Balcony/Terrace- Pet Friendly
- Kitchen
- Parking
CA $553/Night
7 Nights - CA $3,870
House
10.0(58 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
CA $548/Night
7 Nights - CA $3,840
House
6 Bedrooms
2 Baths
12 Guests
2497.23 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $947/Night
7 Nights - CA $6,632
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $432/Night
7 Nights - CA $3,025
Villa
2 Bedrooms
1 Bath
5 Guests
- Pet Friendly
- Parking
- Air Conditioner
Internet
CA $576/Night
7 Nights - CA $4,028
Cottage
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
CA $264/Night
7 Nights - CA $1,849
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $479/Night
7 Nights - CA $3,353
Why Choose Rent By Owner for your Windham Resorts?
What makes our Resorts 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.
Weekly Weather Forecast for Windham
How to Book Your Windham Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. 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 Resorts Amenities
What amenities can you expect?
Our Resorts 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
Other Places to Stay in Windham, ME
Seacoast Adventure
Sebago Lake Basin
Little Falls-South Windham
North Windham
Mercy Primary Care
Maine Wildlife Park
Frequently Asked Questions About Windham Resorts
1. What are the top Resorts 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 Resorts in Windham:
- 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
- EARLY SUMMER SPECIAL* Pet-friendly home w/sandy beach on Little Sebago Lake!
- Lakefront newly renovated 3-bedroom house with two Kitchens in tranquil Windham
- Windham Wind Down-Dock, Kayaks, SUPs, Fishing Rods
- Little Sebago Lake Cottage, WiFi, AC, Dock, 5 min to Windham, 25 min to Portland
- Windham Lakefront: Fire Pit and Modern Comforts
- Serene Modern 4-bedroom Lakefront Home on Highland Lake, 20 mins from Portland
- Cozy Year-round House right outside Portland Maine on Highland Lake.
2. How many Resorts are available in Windham?
Currently, the total number of properties listed by RBO in 2026 is over 110 in the Windham area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Windham.
More Rentals You May Like Near Windham
Hotel
7.0(6 Reviews)
1 Bath
301.39 ft²
- Fireplace/Heating
- Parking
- Internet
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CA $259/Night
7 Nights - CA $1,811
House
9.8(65 Reviews)
3 Bedrooms
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- Fireplace/Heating
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Cottage
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Cottage
8.8(43 Reviews)
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6 Guests
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Cabin
8.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
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CA $573/Night
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Apartment
1 Bedroom
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2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $271/Night
7 Nights - CA $1,899
House
10.0(75 Reviews)
5 Bedrooms
3 Baths
16 Guests
3300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $1,539/Night
7 Nights - CA $10,772
House
10.0(63 Reviews)
4 Bedrooms
2 Baths
9 Guests
3300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $2,389/Night
7 Nights - CA $16,725
House
10.0(35 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $551/Night
7 Nights - CA $3,857
House
10.0(29 Reviews)
4 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
Pool- Ocean View
- Balcony/Terrace
CA $607/Night
7 Nights - CA $4,247
Cabin
10.0(25 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $730/Night
7 Nights - CA $5,108
House
10.0(22 Reviews)
6 Bedrooms
5 Baths
15 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,865/Night
7 Nights - CA $13,055
