Windham Vacation Rentals

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Vacation Rentals in Windham

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.
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, (21)
"The house was really great - plenty of room and a nice and serene. Older house with squeaky and uneven floors but the decor and some modern makeovers made it have great character! Communicating with property manager was very easy and we got prompt responses. The only thing worth mentioning that needs attention is the little bridge to go over to get to the driveway. Luckily we have a higher car but anyone with a regular sedan would have bottomed out and/or possibly got stuck. I’m sure it was...
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
2 duplex
Comfort Duplex, 3 Bedrooms | Private kitchen | Fridge, microwave, oven, dishwasher
2 duplex
3.0 star property
2 duplex
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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, (75)
"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
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)
"It was great. Good location and very clean!"
The price is ￥38,718
￥67,355 total
includes taxes & fees
Jun 12 - Jun 13
NEW TO THE MARKET - 1 block from the beach!
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)
"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
Everybody's favorite Maine beach location
Aerial view
Everybody's favorite Maine beach location
9.2 out of 10, Wonderful, (12)
"The property was updated and very clean. The pillows were not very good, but the bed was great! The location was not where we anticipated. It was very easy checking in and out."
Everybody's favorite Maine beach location
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)
"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 ￥27,877
￥49,292 total
includes taxes & fees
Jun 12 - Jun 13
Large 2BD cottage 10 min to Pier & Beach 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, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
The price is ￥32,117
￥74,392 total
includes taxes & fees
Jun 17 - Jun 18
Elegant condo - walk to Portland's best restaurants & Old Port
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Beach/ocean view
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (176)
"Watching and listening to the ocean was all i needed."
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
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)
"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
Little Miss Cottages
Beach nearby
Little Miss Cottages
2.5 star property
8.2 out of 10, Very Good, (68)
"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
100 feet from the ocean 3 bedroom cottage 420 friendly
Property grounds
100 feet from the ocean 3 bedroom cottage 420 friendly
9.2 out of 10, Wonderful, (13)
"The property was great and a very convenient location to the beach, shops, and pier. They have everything you could possibly need except food and clothing! Very clean, TVs and ACs in every room. The only challenge as others mentioned is parking. It is a tight fit and if your tires are on the sidewalk you can be ticketed. On our second to last day we were approached by the parking patrol and told this. He was super nice and said he wouldn't ticket us but another may. I said we were leaving the...
100 feet from the ocean 3 bedroom cottage 420 friendly
2 min walk to the beach. Pet friendly condo
Beach nearby
2 min walk to the beach. Pet friendly condo
9.0 out of 10, Wonderful, (24)
"Overall a good stay for the price and convenient to everything. Kinda dated and could use some upgrades. "
The price is ￥14,713
￥33,762 total
includes taxes & fees
Jun 10 - Jun 11
2 min walk to the beach. Pet friendly condo
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
Fridge, microwave, oven, stovetop
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
The price is ￥58,934
￥111,312 total
includes taxes & fees
Jun 9 - Jun 10
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
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)
"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 ￥23,231
￥48,280 total
includes taxes & fees
Jun 10 - Jun 11
4 min walk to the beach. A large 3DB Apt. Pets OK
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, (35)
"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
July date's just opened up !!!! Book it now
Exterior
July date's just opened up !!!! Book it now
10.0 out of 10, Exceptional, (274)
"I’ll just start with I’ve never been more at peace leaving a vacation. the kayaking, paddle boating, canoeing did not go to waste,as we found our city selves doing it EVERY DAY! The fires we had, the locals we met, this place is amazing and the memories made are irreplaceable. Thank you so much for providing such a inclusive experience and an unforgettable atmosphere."
July date's just opened up !!!! Book it now
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
Beach nearby, beach towels
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
9.0 out of 10, Wonderful, (49)
"We had a great stay at this charming second floor house. Television does not work. But other than that it was clean, had good parking space and was only a couple steps away from the beach."
The price is ￥23,076
￥48,111 total
includes taxes & fees
Jun 11 - Jun 12
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Living area | TV, Netflix, streaming services
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
8.8 out of 10, Excellent, (20)
"Clean and easy to access, nice property for a short stay. Easy communication."
The price is ￥26,328
￥66,808 total
includes taxes & fees
Jun 11 - Jun 12
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, (1002)
"It was a comfortable stay."
The price is ￥24,950
￥27,195 total
includes taxes & fees
Jun 18 - Jun 19
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, (1562)
"The room (and the whole facility) was super clean, the staff was great when I locked myself out of my room, and the bed was really comfy"
The price is ￥22,311
￥24,319 total
includes taxes & fees
Jun 9 - Jun 10
Casco Bay Hotel, Ascend Hotel Collection
Portland Harbor Hotel
Honeymoon Suite, 1 King Bed | Premium bedding, desk, blackout drapes, iron/ironing board
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1192)
"Property had charm, spacious room and centrally located "
The price is ￥37,746
￥47,657 total
includes taxes & fees
Jun 9 - Jun 10
Portland Harbor Hotel
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.

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windham!

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?

Rent a room in the gorgeous Holt House: This vacation home near Windham has air-conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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

Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

5/5 Excellent
"The room (and the whole facility) was super clean, the staff was great when I locked myself out of my room, and the bed was really comfy"
A verified traveler stayed at Casco Bay Hotel, Ascend Hotel Collection
Posted 15 hours ago
Casco Bay Hotel, Ascend Hotel Collection