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Top Holiday Rentals in Windham

Classic Maine Cabin, Private Waterfront Easy Access to Nearby Amenities

2.0 star property
8.0 out of 10, Very good, (1)
" This cabin is in such a great location! Steps away from the water with kayaks, floats and paddle boards provided. We even saw a bald eagle soar across the ski while floating in front of the dock! The host Braden was extremely accommodating to us and promptly answered all the questions I had. "
Classic Maine Cabin, Private Waterfront Easy Access to Nearby Amenities

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (62)
"Great hotel"
The Weldon Hotel

68 East Grand Ave

3.0 star property
8.8 out of 10, Excellent, (3)
"nice place close to all"
68 East Grand Ave

2 bedroom cottage

9.6 out of 10, Exceptional, (4)
"quiet, clean, short walk to beach"
2 bedroom cottage

In-town no frills 2 bedroom apt

6.0 out of 10, (2)
"The frills of the neighborhood carried into the apartment. Floors and bathrooms seemed clean. Dishes and Keurig filthy - broken window a/c on floor. Broken chairs. No tlc for the property. Neighborhood beyond the stated description- would not recommend . Best to say is that rental car made it out with all windows and tires. Very disappointed "
The price is £154
includes taxes & fees
25 Jun - 26 Jun
In-town no frills 2 bedroom apt

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"Our family of 5 stayed here with our dog. This place has it all and we wanted for nothing. Stocked with towels, everything you would need in the kitchen. There’s even a washer and dryer on site. Right next the beach and a short walk to the pier. It was very clean and well taken care of. We will definitely be back!"
100 feet from the ocean 3 bedroom cottage 420 friendly

Lakefront Cottage: Boat Dock, Patio & Kayaks!

3.0 star property
Lakefront Cottage: Boat Dock, Patio & Kayaks!

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (107)
"Very comfortable, close to shopping and restaurants, clean, easily accessible"
The price is £386
includes taxes & fees
13 Jul - 14 Jul
City Amenities, Casco Bay Sunrises and Natural Beauty

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (112)
"Lovely, clean & great location!"
Gorgeous ocean-front home with stunning beach views

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.6 out of 10, Exceptional, (45)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
The price is £218
includes taxes & fees
8 Jul - 9 Jul
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (150)
"Quaint with a great view."
1 room luxury ocean front studio cottage

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (130)
"Great place. Perfect location if you want to be in the middle of it all."
The price is £444
includes taxes & fees
30 Jun - 1 Jul
Oceanfront Condo! Spectacular Views From Private Large Balcony

Seaside Studio | Accommodates 4| Parking Available

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay. The unit was immaculate and comfortable. The beach was steps away. Definitely recommend a stay!"
Seaside Studio | Accommodates 4| Parking Available

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (59)
"Fantastic "
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Vibrant Motel Suite: Your Cozy Retreat

8.0 out of 10, Very good, (4)
"We loved our stay! Everything was clean, as pictured, and even had some extras on hand. Host made it easy to check in and out. And we loved the Pac-Man machine :) thanks for a great stay!"
The price is £158
includes taxes & fees
25 Jun - 26 Jun
Vibrant Motel Suite: Your Cozy Retreat

Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.

8.6 out of 10, Excellent, (55)
"Easy access and check in. The location was just what we wanted with it close to the beach."
The price is £503
includes taxes & fees
1 Jul - 2 Jul
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

10.0 out of 10, Exceptional, (10)
"Stunning property and great location! "
The price is £479
includes taxes & fees
29 Jun - 30 Jun
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Studio Apartment near downtown Walkable!

6.0 out of 10, (1)
"The listing said "Studio Apartment," but it is really just a bedroom with a bath. A mini-fridge, coffeemaker and microwave oven do not make this a "Studio" in the sense that I understand that word (i.e., a one-room apartment with kitchen and bath). When I went back and looked at the photos in the listing, that should have been obvious to me, but I got hung up on the word "Studio."That said, it was a comfortable room, although the bathroom was stingy on towels (no face cloths, only one hand...
The price is £172
includes taxes & fees
29 Jun - 30 Jun
Studio Apartment near downtown Walkable!

4 min to the beach. Sleeps 6. Pet friendly

6.6 out of 10, (4)
"This property was clean and manager had good communication. Good option if you don’t want to stay in a motel. Only one bed but the kids slept on the two futons. We didn’t spend a lot of time in the room since we were at Palace Playland, mini golf, and surrounding amenities (all in walking distance with teens). Great location off the main strip."
The price is £264
includes taxes & fees
25 Jun - 26 Jun
4 min to the beach. Sleeps 6. Pet friendly
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 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.

What are some of the best holiday rentals that Windham has to offer?

Charming 2-bedroom house with AC, WiFi in lovely Falmouth: This holiday home rental outside of Windham is on a lake, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Windham?

Expedia has 31 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 Sebago Lake Basin and Little Sebago Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Sebago Lake 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.