Windham Vacation Rentals

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Nov 14 - Nov 15
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Nov 14 - Nov 16
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Nov 21 - Nov 23

Vacation Rentals in Windham

Fridge, microwave, stovetop, coffee/tea maker
Spacious Studio Near Sebago Lake

Spacious Studio Near Sebago Lake

2.0 star property
Windham
10.0 out of 10, Exceptional, (1)
"Host was very welcoming and check in was simple "
United States
Michael C.
$112 nightly
The price is $122
Nov 15 - Nov 16
Total with taxes and fees
Spacious Studio Near Sebago Lake
Living area
Serene 1-bedroom house in Windham with Babbling Brook

Serene 1-bedroom house in Windham with Babbling Brook

Windham
Serene 1-bedroom house in Windham with Babbling Brook
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library
The Weldon Hotel

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
$263 nightly
The price is $280
Nov 21 - Nov 22
Total with taxes and fees
The Weldon Hotel
Dining
Sunny Spot with Private Parking.

Sunny Spot with Private Parking.

2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"Had a great stay here! The place was very clean and well-equipped. Convenient parking and a short drive to Portland center. Would stay here again!"
United States
Emre G.
$164 nightly
The price is $179
Nov 16 - Nov 17
Total with taxes and fees
Sunny Spot with Private Parking.
Interior
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

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

Old Orchard Beach
10.0 out of 10, Exceptional, (32)
"Great location and great host. "
United States
Dwight P.
$374 nightly
The price is $408
Nov 16 - Nov 17
Total with taxes and fees
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Exterior detail
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Old Orchard Beach
8.0 out of 10, Very Good, (24)
"Cozy little cotrage"
United States
craig H.
$177 nightly
The price is $193
Nov 17 - Nov 18
Total with taxes and fees
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Property grounds
Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03

Freeport
10.0 out of 10, Exceptional, (6)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
$213 nightly
The price is $232
Dec 2 - Dec 3
Total with taxes and fees
Modern, Luxurious Cabin in the Woods - 03
Fridge, microwave, stovetop, coffee/tea maker
The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable and homey Great location to the outlets. "
United States
Patricia C.
$151 nightly
The price is $164
Nov 16 - Nov 17
Total with taxes and fees
The Outlet Studio, Rustic Comfort w Fireplace
Outdoor dining
Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking

Knightville
9.8 out of 10, Exceptional, (7)
"My husband and I had a wonderful weekend in South Portland and enjoyed the central location and charming touches of Jennifer’s apartment. The space is lovely, exactly as described in the listing. The communication was clear and detailed. We will definitely return!"
United States
Caitlin C.
$179 nightly
The price is $195
Nov 16 - Nov 17
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
Interior
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (125)
"Welcoming small apartment in a beautiful Portland neighborhood. Clean and stocked with everything we needed. Very helpful hosts. "
United States
Annalise M.
$172 nightly
The price is $187
Nov 16 - Nov 17
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
Fridge, microwave, oven, stovetop
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Brunswick
8.8 out of 10, Excellent, (23)
"Great location for baileys island and popham"
United States
Anonymous traveler
$367 nightly
The price is $400
Nov 16 - Nov 17
Total with taxes and fees
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Interior
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

Saco
10.0 out of 10, Exceptional, (13)
"perfect for a couple wanting something that is clean and cozy near beaches in Maine"
United States
Karalyn K.
$257 nightly
The price is $280
Nov 17 - Nov 18
Total with taxes and fees
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
Fridge, microwave, oven, stovetop
Beach across the Street. Pets OK

Beach across the Street. Pets OK

Old Orchard Beach
8.6 out of 10, Excellent, (31)
"Perfect spot! Right near the beach and walking distance to all the best places. Very clean and chill little place perfect for what I was going for."
United States
Dom C.
$166 nightly
The price is $181
Nov 17 - Nov 18
Total with taxes and fees
Beach across the Street. Pets OK
Exterior
Cheerful 1 bedroom cottage only 50ft from beach

Cheerful 1 bedroom cottage only 50ft from beach

Old Orchard Beach
10.0 out of 10, Exceptional, (2)
"Amazing!"
Canada
Annie B.
$214 nightly
The price is $233
Nov 16 - Nov 17
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
Beach nearby
Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!

Willard Beach
10.0 out of 10, Exceptional, (60)
"Near beach, walking, bakery, ice cream and close to great restaurants. Lovely spot and easily accommodated 2 couples. Would stay here again!"
United States
Kirstin D.
$318 nightly
The price is $346
Dec 2 - Dec 3
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
Interior
Serenity between the lakes and seashore

Serenity between the lakes and seashore

Westbrook
9.8 out of 10, Exceptional, (24)
"Good location near lots of hiking and not far from Portland "
United States
Laura P.
$285 nightly
The price is $311
Nov 29 - Nov 30
Total with taxes and fees
Serenity between the lakes and seashore
Interior
Bright & Sunny West End Apartment with Private Parking.

Bright & Sunny West End Apartment with Private Parking.

West End
10.0 out of 10, Exceptional, (45)
"Adorable apartment for our family of 5 to spend a night. Great location in town. "
United States
Brandy C.
$234 nightly
The price is $255
Nov 16 - Nov 17
Total with taxes and fees
Bright & Sunny West End Apartment with Private Parking.
TV, books
Back Cove Gem ★ 5 Min to Old Port ★ Bright and New

Back Cove Gem ★ 5 Min to Old Port ★ Bright and New

Oakdale
10.0 out of 10, Exceptional, (43)
"Perfect accommodations! My best friend and I, along with my husband, had the best time. The beds were dreamy and the kitchen had all the supplies we needed. Quiet neighborhood within a 5 minute Uber to downtown- our first trip to Portland and we hope to be back soon!"
United States
Tara (Harris) K.
$288 nightly
The price is $314
Nov 16 - Nov 17
Total with taxes and fees
Back Cove Gem ★ 5 Min to Old Port ★ Bright and New
Property grounds
Saco/Old Orchard Beach Get Away

Saco/Old Orchard Beach Get Away

2.0 star property
Saco
10.0 out of 10, Exceptional, (3)
"the apartment was perfect! It was clean and comfortable. Bed and pillows were great. Walking distance to some really sweet coffe shops. We fell in love with Swell! Thank you for being so patient with us as navigated some excited kids after long days of playing lacrosse! Great hosts!! "
United States
Jessica L.
$328 nightly
The price is $358
Nov 15 - Nov 16
Total with taxes and fees
Saco/Old Orchard Beach Get Away
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

Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

10/10 Excellent
"Easy check in/out "
Keomany 1-night trip
Posted 2 days ago
Ramada Plaza by Wyndham 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 $140 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?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This vacation home rental near Windham is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 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 32 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 Jordan Bay.

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.