A white church with a steeple and red accents, surrounded by autumn trees.

Windham Vacation Rentals

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Check prices for these dates

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

Our top choices for Windham vacation 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.
$389 nightly
The price is $424
Nov 9 - Nov 10
Total with taxes and fees
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
$77 nightly
The price is $78
Nov 9 - Nov 10
Total with taxes and fees
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.
$75 nightly
The price is $76
Nov 5 - Nov 6
Total with taxes and fees
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
9.2 out of 10, Wonderful, (22 reviews)
"We really appreciated our stay!"
United States
Anonymous traveler
$110 nightly
The price is $120
Nov 6 - Nov 7
Total with taxes and fees
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.
$252 nightly
The price is $275
Nov 5 - Nov 6
Total with taxes and fees
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.
$673 nightly
The price is $741
Nov 23 - Nov 24
Total with taxes and fees
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
$266 nightly
The price is $290
Nov 5 - Nov 6
Total with taxes and fees
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, (25 reviews)
"Location was convenient to everything and building was super secure."
United States
Rose
$121 nightly
The price is $122
Nov 12 - Nov 13
Total with taxes and fees
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, (18 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
$367 nightly
The price is $400
Dec 1 - Dec 2
Total with taxes and fees
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.
$423 nightly
The price is $461
Nov 8 - Nov 9
Total with taxes and fees
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, (129 reviews)
"Really nice room and location"
United States
Victoria
$263 nightly
The price is $280
Nov 16 - Nov 17
Total with taxes and fees
The Weldon Hotel
A bathroom with a glass-enclosed shower, a toilet, a sink, and a mirror.

12. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (34 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$142 nightly
The price is $155
Nov 8 - Nov 9
Total with taxes and fees
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.
$149 nightly
The price is $163
Nov 10 - Nov 11
Total with taxes and fees
Bright & Spacious Apartment with Amazing Shower
A kitchen with wooden cabinets, a black refrigerator, a microwave, a stove, 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
$233 nightly
The price is $254
Nov 18 - Nov 19
Total with taxes and fees
Cozy 2-bedroom house with shared beach access to Sebago Lake
A modern kitchen with a built-in oven, a dining area with a yellow sofa, and a kitchen island.

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.
$222 nightly
The price is $244
Nov 5 - Nov 6
Total with taxes and fees
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.
$192 nightly
The price is $209
Nov 8 - Nov 9
Total with taxes and fees
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A black console table with a mirror, a lamp, books, and a potted plant.

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.
$240 nightly
The price is $264
Nov 5 - Nov 6
Total with taxes and fees
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.
$305 nightly
The price is $332
Nov 10 - Nov 11
Total with taxes and fees
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)
"Excellent property in Portland. Clean with amenities needed for any stay. Easy access to downtown. Hosts communicate exceptionally well and property is everything it promotes!"
United States
Adam Y.
$308 nightly
The price is $336
Nov 8 - Nov 9
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
A house with a wooden staircase leading to a door marked with the number 50.

20. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (108 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
$232 nightly
The price is $252
Nov 8 - Nov 9
Total with taxes and fees
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
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

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"Staff was very friendly and accommodating. Free parking. Clean rooms. Great rates."
Kevin 1-night trip
Posted 3 hours ago
Clarion Pointe South Portland

Find out more about Windham

Everything you need to know about Windham vacation rentals

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

Windham vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $120 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Windham?

Yes, we offer vacation rentals in Windham near Seacoast Adventure, or you can go with a more remote option if you're looking for extra privacy while you relax. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffeehouses during your trip.

What are some of the best vacation rentals in Windham?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This vacation home rental near Windham is located on the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Windham?

Expedia has 37 vacation 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 vacation rentals like in Windham?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Windham. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.