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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Windham holiday rentals

A dining table with two black cups and saucers, a wooden vase with flowers, and a window with white frames.

1. 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 £291
includes taxes & fees
8 Nov - 9 Nov
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
A backyard with a wooden deck, a small staircase, and a wooden fence.

2. 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 £60
includes taxes & fees
9 Nov - 10 Nov
Great suburban location close to town!
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

3. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.0 out of 10, Very good, (17 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 £62
includes taxes & fees
11 Nov - 12 Nov
Portland 1-bedroom with enclosed porch & parking
A gym with treadmills, elliptical machines, and exercise balls.

4. 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 £91
includes taxes & fees
11 Nov - 12 Nov
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

5. 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 £208
includes taxes & fees
9 Nov - 10 Nov
THE LILLIPAD.Off-grid A frame. Sebago lake region!
A spacious kitchen with a large island, wooden beams, and a view of the outdoors.

6. Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit
Gray
9.8 out of 10, Exceptional, (8 reviews)
"The host was lovely, very accommodating and responsive. We had a great time!"
United States
Beth L.
Waterfront Access with Kayaks, Private Deck and a Firepit
A room with a leather armchair, ottoman, wooden cabinet with decorative items, and a television mounted on the wall.

7. 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 £217
includes taxes & fees
29 Nov - 30 Nov
Cozy 1-bedroom cottage in soothing Standish with AC
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

8. 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 £93
includes taxes & fees
12 Nov - 13 Nov
Studio Apartment near downtown Walkable!
A multi-story building with a stone facade, large windows, and a corner entrance.

9. 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 £303
includes taxes & fees
7 Dec - 8 Dec
Evalina Hotel
A two-story house with a covered front porch and a brick foundation.

10. 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 £344
includes taxes & fees
9 Nov - 10 Nov
Three Gables Back Cove by Everrow
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

11. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (130 reviews)
"Really nice room and location"
United States
Victoria
The price is £202
includes taxes & fees
1 Dec - 2 Dec
The Weldon Hotel
A living room with a sofa, armchairs, a coffee table, and a potted plant.

12. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (35 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is £116
includes taxes & fees
8 Nov - 9 Nov
Beautiful 1st Floor Apartment & Amazing Shower
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

13. 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 £124
includes taxes & fees
10 Nov - 11 Nov
Bright & Spacious Apartment with Amazing Shower
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

14. 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 £191
includes taxes & fees
18 Nov - 19 Nov
Cozy 2-bedroom house with shared beach access to Sebago Lake
A brick wall with a logo and the text 'THE SEND BREWING CO.'

15. 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 £156
includes taxes & fees
12 Nov - 13 Nov
Sunny Spot with Private Parking
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

16. 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)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is £158
includes taxes & fees
8 Nov - 9 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A brick wall with a logo and the text 'THE SEND BREWING CO.'

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

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is £185
includes taxes & fees
19 Nov - 20 Nov
Peaceful & minutes from Old Port w/private parking
A cabin with two chairs facing a fire pit, surrounded by trees.

18. 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 £247
includes taxes & fees
10 Nov - 11 Nov
Cabin w/ bath + kitchenette | Hot tub add-on - 03
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

19. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.4 out of 10, Exceptional, (97 reviews)
"Was great for our few days in Portland! Having a designated parking space was great and the location was convenient for everything we wanted to do."
United States
Britney G.
The price is £253
includes taxes & fees
8 Nov - 9 Nov
Walk to Old Port ♦ West End Condo ♦ Parking
A door with a screen, a bird statue, and a house number sign.

20. 1200 sq ft ♦ West End Gem ♦ Steps from Old Port

1200 sq ft ♦ West End Gem ♦ Steps from Old Port
West End
9.2 out of 10, Wonderful, (110 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
The price is £190
includes taxes & fees
8 Nov - 9 Nov
1200 sq ft ♦ West End Gem ♦ Steps from Old Port
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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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

Clean and modern hotel. Friendly and helpful staff and great indoor swimming pool
United Kingdom
Chris
Reviewed November 12, 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, 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 £201 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 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.