Windham Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Windham holiday rentals

A house surrounded by trees and a body of water.

1. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is AU$968
includes taxes & fees
19 Nov - 20 Nov
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
A dining table with two black cups and saucers, a wooden vase with flowers, and a window with white frames.

2. Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
Westbrook
10.0 out of 10, Exceptional, (16 reviews)
"Excellent location, the hosts are very responsive and an absolute pleasure to work with. The home was clean, inviting and easy to check in."
United States
Bianca L.
The price is AU$587
includes taxes & fees
17 Nov - 18 Nov
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
A compact living space with a sofa, a coffee table, a TV on a stand, a floor lamp, and a bookshelf.

3. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.4 out of 10, Exceptional, (6 reviews)
"We were staying here for the sake of being able to see a show at Good Theater. The theater itself ended up being within walking distance, and same for a few different places to eat! This worked out great for our plans :)"
United States
Kaley
The price is AU$100
includes taxes & fees
16 Nov - 17 Nov
Great suburban location close to town!
A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

4. THE LILLIPAD.Off-grid A frame. Sebago lake region!

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Standish
9.8 out of 10, Exceptional, (16 reviews)
"Had a wonderful overnight - was perfect weekend getaway. Was great being in nature!"
United States
Alex D.
The price is AU$399
includes taxes & fees
15 Nov - 16 Nov
THE LILLIPAD.Off-grid A frame. Sebago lake region!
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

5. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (131 reviews)
"It was so spacious, kitchen area was well kept and they have QR codes to help travels understand how to use certain things"
United States
Branden
The price is AU$402
includes taxes & fees
29 Nov - 30 Nov
The Weldon Hotel
A narrow hallway with wooden flooring leading to a bedroom with a bed and a nightstand.

6. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
7.8 out of 10, Good, (19 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
The price is AU$105
includes taxes & fees
16 Nov - 17 Nov
Portland 1-bedroom with enclosed porch & parking
A modern room with a desk, chair, and large window.

7. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.4 out of 10, Exceptional, (23 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is AU$177
includes taxes & fees
14 Nov - 15 Nov
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A multi-story building with a stone facade, large windows, and a flat roof with dormer windows.

8. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (19 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is AU$582
includes taxes & fees
14 Dec - 15 Dec
Evalina Hotel
A hallway with wooden beams, a hanging clothes rack, a stone-tiled floor, and a door leading to another room.

9. Cozy 1-bedroom cottage in soothing Standish with AC

Cozy 1-bedroom cottage in soothing Standish with AC
Standish
10.0 out of 10, Exceptional, (4 reviews)
"Amazing property & so many things to do around the area, we will definitely try to come back!!"
United States
Alyssa
The price is AU$422
includes taxes & fees
29 Nov - 30 Nov
Cozy 1-bedroom cottage in soothing Standish with AC
A modern kitchen with a large island, bar stools, and a view through large windows.

10. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (17 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is AU$1,100
includes taxes & fees
30 Nov - 1 Dec
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A sandy beach with people and a play structure.

11. Sunny Spot with Private Parking

Sunny Spot with Private Parking
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
The price is AU$291
includes taxes & fees
16 Nov - 17 Nov
Sunny Spot with Private Parking
A porch with a green exterior, a black railing, and a chair with a cushion.

12. Three Gables Back Cove by Everrow

Three Gables Back Cove by Everrow
Rosemont
10.0 out of 10, Exceptional, (15 reviews)
"GoodLocation, very clean. Would stay again "
United States
Carly B.
The price is AU$695
includes taxes & fees
16 Nov - 17 Nov
Three Gables Back Cove by Everrow
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

13. Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is AU$384
includes taxes & fees
19 Nov - 20 Nov
Cozy 2-bedroom house with shared beach access to Sebago Lake
A cabin with two chairs facing a fire pit, surrounded by trees.

14. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Cabin w/ bath + kitchenette | Hot tub add-on - 03
Freeport
9.8 out of 10, Exceptional, (10 reviews)
"A lovely glamping facility with several different types of structure in a quiet, wooded area just a couple miles from downtown Freeport. They've built a beautiful spa with sauna, cold plunge, hot tub, and soaking pool, the unit we stayed in was bright and airy, had an outdoor fire pit. We stayed three nights, will definitely stop here again!"
United States
Kirt v.
The price is AU$427
includes taxes & fees
15 Nov - 16 Nov
Cabin w/ bath + kitchenette | Hot tub add-on - 03
A beach with people, a play structure, and a view of the sea.

15. Peaceful & minutes from Old Port w/private parking

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (14 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is AU$357
includes taxes & fees
19 Nov - 20 Nov
Peaceful & minutes from Old Port w/private parking
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

16. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (27 reviews)
"Location was convenient to everything and building was super secure."
United States
Rose
The price is AU$180
includes taxes & fees
19 Nov - 20 Nov
Studio Apartment near downtown Walkable!
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

17. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Everything you need, very clean, close to the water and easily walkable to many things. Would definitely stay again!"
United States
Ryan B.
The price is AU$307
includes taxes & fees
16 Nov - 17 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A living room with a sofa, a coffee table, a TV, and a plant.

18. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (35 reviews)
"Good price, decent location, clean, and affordable"
United States
Chloe C.
The price is AU$205
includes taxes & fees
18 Nov - 19 Nov
Beautiful 1st Floor Apartment & Amazing Shower
A modern kitchen with wooden cabinets, a black refrigerator, and a dining area with a wooden table and chairs.

19. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (29 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
The price is AU$205
includes taxes & fees
19 Nov - 20 Nov
Bright & Spacious Apartment with Amazing Shower
A beach with clear water, people swimming, and houses in the background.

20. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard By the Sea - 30 ft to the beach- 2nd floor
Willard
10.0 out of 10, Exceptional, (16 reviews)
"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."
United States
Gerald B.
The price is AU$592
includes taxes & fees
17 Nov - 18 Nov
Willard By the Sea - 30 ft to the beach- 2nd floor
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.
View all properties

Find holiday rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Windham Hotel Reviews

A bright room with large windows, two armchairs, a small table, and a chandelier.
Dormir

Dormir

Dormir
Windham

10/10 Excellent

One of the only nice places to stay near Sebago. Reasonable prices and super nice employees with good suggestions for food and hiking. Highly recommend compared to other local options. Clean and new accomodations.
Australia
James
Reviewed October 5, 2019
Dormir

Find out more about Windham

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, 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 favourite 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 depend 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 AU$100 per night. Entering your travel dates in the search wizard might find you 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 Seacoast Adventure, 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?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This holiday home rental outside of Windham is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Windham?

Expedia has 37 holiday rentals for your stay in Windham.

What can I see and do in Windham?

Little Sebago Lake and Sebago Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Seacoast Adventure. Other places in town to visit include Sebago Lake Basin and Forest Lake.

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.