Windham Vacation Rentals

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Vacation Rentals in Windham

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
Property grounds
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
8.4 out of 10, Very Good, 22 reviews
"Beautiful and peaceful setting on the lake. Close enough to Portland and other activities but quiet and relaxed at the cottage."
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
Pet-friendly! Modern and spacious 3-bedroom home on the Pleasant River.
Fridge, microwave, oven, stovetop
Pet-friendly! Modern and spacious 3-bedroom home on the Pleasant River.
Pet-friendly! Modern and spacious 3-bedroom home on the Pleasant River.
2 duplex
Comfort Duplex, 3 Bedrooms | Private kitchen | Fridge, microwave, oven, dishwasher
2 duplex
3.0 star property
2 duplex
NEW TO THE MARKET - 1 block from the beach!
Beach nearby
NEW TO THE MARKET - 1 block from the beach!
10.0 out of 10, Exceptional, 7 reviews
"We absolutely loved staying here. The place was very clean and comfortable. We enjoyed walking around and exploring."
The price is ￥29,796
per night
Jun 18 - Jun 19
NEW TO THE MARKET - 1 block from the beach!
Gorgeous ocean-front home with stunning beach views
On the beach
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, 76 reviews
"Great little condo. Right on the beach! Balcony is wonderful, as is the view from the master. Second bedroom is definitely a “kids” room with the two bunk beds. Garage was great for a car, would not fit the height of a truck"
Gorgeous ocean-front home with stunning beach views
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
Beach
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
7.4 out of 10, Good, 25 reviews
"The unit has a really nice view of downtown and the pier. Cool view of the ferris wheel lit up at night. At first glance, the unit is nicely decorated. However, it needs to be refreshed - there are chunks missing out of the walls, things falling apart, ongoing water damage next to the tub. Maintenance from the building came by on the first morning of the stay to check on the kitchen sink because there was a massive leak happening to the unit below. Overall, it seemed as if no one has been...
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
2 min walk to the beach. Pet friendly condo
Beach nearby
2 min walk to the beach. Pet friendly condo
8.8 out of 10, Excellent, 25 reviews
"Overall a good stay for the price and convenient to everything. Kinda dated and could use some upgrades. "
The price is ￥27,487
per night
Jun 17 - Jun 18
2 min walk to the beach. Pet friendly condo
Little Miss Cottages
Beach nearby
Little Miss Cottages
2.5 star property
8.2 out of 10, Very Good, 68 reviews
"Perfect place for a family to stay for a fair price if you want to stay a few nights and tour around the rest of Maine. Beach was wonderful! "
Little Miss Cottages
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
Exterior
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
9.8 out of 10, Exceptional, 12 reviews
"This is a great spot to stay no matter what time of the year!! Completely enjoyed my stay!!"
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
4 min walk to the beach. A large 3DB Apt. Pets OK
Fridge, microwave, oven, stovetop
4 min walk to the beach. A large 3DB Apt. Pets OK
8.6 out of 10, Excellent, 7 reviews
"We found this place and booked after seeing it was pet friendly and close to the beach which was a must for our beach loving family and pups. Our stay was lovely- it’s a few blocks to the beach and into the main town area. The place was clean, had a good amount of space, was quiet, and a small deck area to sit outside. Communications with the host were easy and they checked in on us part way through to ensure our stay was going well."
The price is ￥20,419
per night
Jun 17 - Jun 18
4 min walk to the beach. A large 3DB Apt. Pets OK
Elegant condo - walk to Portland's best restaurants & Old Port
Private kitchen | Fridge, microwave, oven, stovetop
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, 47 reviews
"My two sisters and I loved everything about the place especially the kitchen and the temperature control via AC or heat. The only concern about the place is that it took 1-3 tries each time we had to unlock the front door by code. There was supposed to be music to help but couldn't really hear anything. May need some attention but have to admit we never alerted anyone at the time thinking it was related to our ineptitude! I tried to do this review on the Vacasa site but the page never came up...
The price is ￥33,089
per night
Jun 18 - Jun 19
Elegant condo - walk to Portland's best restaurants & Old Port
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
Property grounds
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
8.2 out of 10, Very Good, 33 reviews
"I rated this property a 4 and not lower because of its location. It is front-facing to the ocean, and that is always a gem in my book. Sleeping to the sound of the waves is amazing. The property management (Vacasa) was flawless in their communication and the housekeeping staff did a great job cleaning what they were responsible for cleaning. BUT....... this unit is in dire need of some deep cleaning and at a minimum some TLC in painting and in fixing what doesn't work (i.e., windows, toilet...
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
Fridge, microwave, oven, stovetop
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
The price is ￥71,756
per night
Jun 17 - Jun 18
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
Everybody's favorite Maine beach location
Aerial view
Everybody's favorite Maine beach location
9.4 out of 10, Exceptional, 13 reviews
"The property was clean and spacious for four 25 year old men to comfortably stay for the weekend."
Everybody's favorite Maine beach location
350 Yards to the beach. Pet friendly!
Beach
350 Yards to the beach. Pet friendly!
8.4 out of 10, Very Good, 24 reviews
"Unit was clean but small enough for privacy"
The price is ￥21,990
per night
Jun 20 - Jun 21
350 Yards to the beach. Pet friendly!
Oceanfront Condo! Spectacular Views From Private Large Balcony
Beach/ocean view
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, 114 reviews
"I loved the location!!! Great little place...restaurant downstairs was great."
The price is ￥77,750
per night
Jul 9 - Jul 10
Oceanfront Condo! Spectacular Views From Private Large Balcony
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.4 out of 10, Exceptional, 17 reviews
"The cottage was clean and accurately described. It was perfect for our needs and we are already looking forward to staying there again in the future."
The price is ￥28,273
per night
Jun 17 - Jun 18
Large 2BD cottage 10 min to Pier & Beach Pets ok
East Grand Ave Fabulous Cottage
Beach
East Grand Ave Fabulous Cottage
9.0 out of 10, Wonderful, 112 reviews
"Very good location. Walked everywhere and very close to the beach. The owner was super receptive when there was an understandable appliance problem. I would definitely return."
East Grand Ave Fabulous Cottage
Beach House ∆ Prime Location ∆ Steps to the Ocean
3 bedrooms, desk, iron/ironing board, travel crib
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, 36 reviews
"The cottage was very nice but the write-up was a little misleading. For example ocean views are very limited—mostly see rooftops, half bath was on ground floor, and stairs to main living area."
Beach House ∆ Prime Location ∆ Steps to the Ocean
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Fridge, microwave, oven, stovetop
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
8.8 out of 10, Excellent, 20 reviews
"Clean and easy to access, nice property for a short stay. Easy communication."
The price is ￥28,901
per night
Jul 1 - Jul 2
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
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See all available properties in Windham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Windham you may be interested in

Microtel Inn & Suites By Wyndham Windham
Exterior
Microtel Inn & Suites By Wyndham Windham
3.0 star property
8.8 out of 10, Excellent, 1,001 reviews
"It was a comfortable stay."
The price is ￥25,304
per night
Jun 16 - Jun 17
Microtel Inn & Suites By Wyndham Windham
Casco Bay Hotel, Ascend Hotel Collection
Lobby
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.6 out of 10, Excellent, 1,599 reviews
"Solid stay and easy check in process "
The price is ￥15,550
per night
Jun 16 - Jun 17
Casco Bay Hotel, Ascend Hotel Collection
The Westin Portland Harborview
Water view
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, 1,049 reviews
"Kids love the cookies right by the entrance. "
The price is ￥39,048
per night
Jun 16 - Jun 17
The Westin Portland Harborview
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Frequently asked questions

Are there vacation rentals in Windham?

Yes, we offer vacation rentals in Windham near Maine Wildlife Park, or you can go with a more remote option if you're looking for extra privacy while you relax. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffeehouses during your trip.

What are some of the best vacation rentals in Windham?

Elegant condo - walk to Portland's best restaurants & Old Port: This vacation home near Windham is in the city center and equipped with air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Windham?

Expedia has 31 vacation rentals for your stay in Windham.

What can I see and do in Windham?

Family-friendly attractions include Maine Wildlife Park and Seacoast Adventure, whereas Little Sebago Lake and Sebago Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Sebago Lake Basin and Jordan Bay.

What are vacation rentals like in Windham?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Windham. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.

Recent reviews of Windham properties
Expedia verified reviews

Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

5/5 Excellent
"Close to everything"
A verified traveler stayed at Hilton Garden Inn Portland Downtown Waterfront
Posted 15 hours ago
Hilton Garden Inn Portland Downtown Waterfront