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Top Holiday Rentals in Windham

Property grounds
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
8.4 out of 10, Very good, (20)
"The house was good for 4 adults and 2 kids, it was clean and well stocked. It stayed warm during the colder nights. The check in and check out was really chill. The lake was beautiful!"
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
Comfort Duplex, 3 Bedrooms | Private kitchen | Fridge, microwave, oven, dishwasher
2 duplex
3.0 star property
The price is £299
includes taxes & fees
4 May - 5 May
2 duplex
On the beach
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (74)
"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
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Fridge, stovetop, dishwasher, coffee/tea maker
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (14)
"Great place- location is easy to get to - great furniture and high end appliances - clean and chic!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
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
Property grounds
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (124)
"We really enjoyed our stay. We loved being able to walk to the Eastern Promenade. The beds, including the sofa bed were very comfortable. Very cute and cozy There are stairs to enter the building for anyone with mobility issues. If you are unfamiliar with older buildings, the radiators do make some noise while heating in the winter."
The price is £246
includes taxes & fees
16 May - 17 May
Glorious getaway on Portland's Eastern Promenade.
Property grounds
Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦
10.0 out of 10, Exceptional, (9)
"Tons of space and so close to the beach."
The price is £556
includes taxes & fees
8 May - 9 May
Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦
Beach/ocean view
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (111)
"A good room/property. Check in & out was easy. Beds were a little firm, but everything else was good."
The price is £264
includes taxes & fees
6 May - 7 May
Oceanfront Condo! Spectacular Views From Private Large Balcony
Beach
East Grand Ave Fabulous Cottage
9.0 out of 10, Wonderful, (110)
"Good location, owner was very responsive to our needs."
East Grand Ave Fabulous Cottage
Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, (50)
"Comfortable, clean, very well decorated apartment in a pleasant, walkable neighborhood. I highly recommend this property."
The price is £431
includes taxes & fees
5 May - 6 May
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
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
Beach/ocean view
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (174)
"Even with a snow/ice storm, the beach doesn’t disappoint! Beautiful sunrises, sunsets, and waves crashing. The condo was warm and cozy and I was very happy to be able to watch the Bruins on tv. Already planned my next visit!"
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Beach nearby, beach towels
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
9.0 out of 10, Wonderful, (46)
"The location was perfect so close to the beach! Place could use some more glassware and a grill to cook out. However, it was overall a very nice getaway! Group from New York"
The price is £254
includes taxes & fees
5 May - 6 May
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
Fridge, microwave, oven, coffee/tea maker
4 min walk to the beach. Large 1BD Pets Ok
10.0 out of 10, Exceptional, (6)
"This please was very nice and perfect for just my fiancé and I. Very clean and spacious! We would book again! Thank you"
The price is £204
includes taxes & fees
6 May - 7 May
4 min walk to the beach. Large 1BD Pets Ok
2 bedrooms, cots/infant beds, Internet, bed sheets
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
7.6 out of 10, Good, (4)
"This home was clean, bright and comfortable. Great location, no issues. Would definitely stay here again."
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
TV
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
7.4 out of 10, Good, (24)
"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
Beach nearby
2 min walk to the beach. Pet friendly condo
9.0 out of 10, Wonderful, (21)
"such a cute little place. We enjoyed staying here across from the beach so it was quick access."
The price is £178
includes taxes & fees
6 May - 7 May
2 min walk to the beach. Pet friendly condo
Exterior
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.2 out of 10, Wonderful, (15)
"The house was cozy and well equipped. We had a wonderful time."
The price is £177
includes taxes & fees
6 May - 7 May
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior
Relaxing loft style cabin getaway for 2. plenty to relax and enjoy!
10.0 out of 10, Exceptional, (273)
"This place is perfect for couples! Private, romantic and outdoor lovers dream! I cannot say enough! The pond is gorgeous and fishing access is wonderful! If the place comes up for sale we'll buy it!"
Relaxing loft style cabin getaway for 2. plenty to relax and enjoy!
View from property
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (75)
"This is a lovely little apartment, and we were very comfortable. I agree with the owner’s statement about the steps being steep; there is no landing at the top of these steps. We brought smaller bags, and that helped! I wouldn’t attempt this with a baby or a toddler. Everybody else: enjoy!"
The price is £205
includes taxes & fees
5 May - 6 May
Adorable Portland getaway on the Eastern Promenade
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 Holiday Rental Travel Info

Number of holiday rentals
7
Popular accommodation
Windham private holiday 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

Exterior
Microtel Inn & Suites By Wyndham Windham
3.0 star property
8.8 out of 10, Excellent, (1001)
"Price was excellent for the stay, decent breakfast for my kids. Pool area and gym was clean. I recommend this place. "
The price is £109
includes taxes & fees
5 May - 6 May
Microtel Inn & Suites By Wyndham Windham
Bar (on property)
Ramada Plaza by Wyndham Portland
3.0 star property
7.6 out of 10, Good, (1006)
"It was fine. "
The price is £90
includes taxes & fees
7 May - 8 May
Ramada Plaza by Wyndham Portland
Honeymoon Suite, 1 King Bed | Premium bedding, desk, blackout curtains, iron/ironing board
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1177)
"The location was perfect the water dispenser gave me questionable water, but they had some Poland springs stocked in the fridge."
The price is £171
includes taxes & fees
27 May - 28 May
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.

Everything you need to know about Windham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windham holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham holiday rentals we have selected for you start as low as £177 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 holiday 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 holiday.

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 holiday rentals in Windham?

Yes, there are holiday rentals in Windham close to Maine Wildlife Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffee shops during your trip.

How many holiday rentals are there in Windham?

Expedia has 33 holiday 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 holiday rentals like in Windham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windham. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

Recent reviews of Windham properties
Expedia verified reviews