Holiday Rentals in Windham

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

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, (63)
"We had a wonderful stay. The room was super clean, spacious, cool and comfortable. The self check in process was easy and although there is no front desk, the staff was very responsive."
The price is €416
includes taxes & fees
13 Jul - 14 Jul
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

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 €252
includes taxes & fees
8 Jul - 9 Jul
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

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

2 bedroom cottage

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

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, (113)
"The condo was perfect. The views were gorgeous. You could see the ocean the moment you opened the door! It was clean and comfortable. We loved every minute and didnt want to leave. "
Gorgeous ocean-front home with stunning beach views

AmongstTheAspens - Tiny House in a serene location

AmongstTheAspens - Tiny House in a serene location

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 €205
includes taxes & fees
6 Jul - 7 Jul
In-town no frills 2 bedroom apt

Lakefront Cottage: Boat Dock, Patio & Kayaks!

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

Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

8.0 out of 10, Very good, (11)
"The view , the quiet, the autumn colors ,"
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

Waterfront Maine cottage! Next to Sebago Lake State Park!

10.0 out of 10, Exceptional, (18)
"We had a great stay! Thank you very much for a great vacation!"
Waterfront Maine cottage! Next to Sebago Lake State Park!

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

7.4 out of 10, Good, (26)
"The cute apartment was clean with super comfy beds and very convenient to everything in OOB."
The price is €544
includes taxes & fees
5 Jul - 6 Jul
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

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 €677
includes taxes & fees
23 Jul - 24 Jul
Oceanfront Condo! Spectacular Views From Private Large Balcony

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 €938
includes taxes & fees
13 Jul - 14 Jul
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

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 €595
includes taxes & fees
10 Jul - 11 Jul
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.

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 €218
includes taxes & fees
21 Jul - 22 Jul
Vibrant Motel Suite: Your Cozy Retreat

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

Cozy and Quiet beautiful home 1 Bedroom private bathroom Portland with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet beautiful home 1 Bedroom private bathroom Portland with WiFi, AC
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach: This holiday home rental outside of Windham offers a garden, a selection of games and a BBQ 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 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.