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, (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
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
2 duplex
3.0 star property
2 duplex
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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)
"We absolutely loved staying here. The place was very clean and comfortable. We enjoyed walking around and exploring."
The price is CA $220
CA $444 total
includes taxes & fees
Jun 12 - Jun 13
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, (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
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
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 CA $131
CA $300 total
includes taxes & fees
Jun 10 - Jun 11
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)
"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)
"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)
"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 CA $206
CA $429 total
includes taxes & fees
Jun 10 - Jun 11
4 min walk to the beach. A large 3DB Apt. Pets OK
Elegant condo - walk to Portland's best restaurants & Old Port
Private kitchen
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 CA $273
CA $642 total
includes taxes & fees
Jun 15 - Jun 16
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)
"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
1 Bedroom Downtown Condo, Walk to the Beach & Pier
Beach
1 Bedroom Downtown Condo, Walk to the Beach & Pier
9.6 out of 10, Exceptional, (14)
"This property didn’t disappoint, it was in a great location only minutes away from the beach and the broad walk. Property was clean and the property managers were easy to get a hold of through my email when I had a question. Would definitely recommend to anyone who needs a place to stay in Old Orchard Beach!"
1 Bedroom Downtown Condo, Walk to the Beach & Pier
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
Fridge, microwave, oven, stovetop
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
The price is CA $520
CA $992 total
includes taxes & fees
Jun 10 - Jun 11
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
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
350 Yards to the beach. Pet friendly!
Beach
350 Yards to the beach. Pet friendly!
8.4 out of 10, Very good, (24)
"Unit was clean but small enough for privacy"
The price is CA $131
CA $300 total
includes taxes & fees
Jun 11 - Jun 12
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)
"I loved the location!!! Great little place...restaurant downstairs was great."
The price is CA $323
CA $549 total
includes taxes & fees
Jun 10 - Jun 11
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)
"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 CA $248
CA $438 total
includes taxes & fees
Jun 12 - Jun 13
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, (111)
"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, (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
Don't see what you're looking for?
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.

Windham Vacation Rental Travel Info

Number of vacation rentals
7
Popular accommodation
Windham private vacation homes
Known landmarks
Seacoast Adventure, Maine Wildlife Park and Southworth Planetarium
International airport
Portland, ME (PWM-Portland Intl. Jetport)

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 CA $222
CA $242 total
includes taxes & fees
Jun 10 - Jun 11
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, (1570)
"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 CA $147
CA $161 total
includes taxes & fees
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, (1057)
"All staff were super friendly and helpful. Room on 8th floor was huge, corner room, good views and could just see the ocean. We were disappointed the 15th floor bar and restaurant was closed the evening we were there. But plenty of restaurants just 10 to 20 minutes walk down to the old port area. Some areas, especially the exterior, need some tlc!"
The price is CA $291
CA $331 total
includes taxes & fees
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.

Everything you need to know about Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windham vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham vacation rentals we have selected for you start as low as CA $131 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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
"Liked most everything about our 5- night stay. Friendly and helpful front desk staff. Also special shout out to Maggie (GSM) who resolved an issue quickly and to our satisfaction. Only negative I can think of is the Housekeeping staff needs to do a better job with cleaning the room. Especially since ours was a longer stay. "
A verified traveller from Hartsdale stayed at Hilton Garden Inn Portland Downtown Waterfront
Posted 1 day ago
Hilton Garden Inn Portland Downtown Waterfront