Search and Rent Windham Condos

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Our top choices for Windham condo rentals

9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
$211 nightly
The price is $230
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy, Elegant and Bright 2 bed in the East End
10.0 out of 10, Exceptional, (63)
"We had a wonderful week here. Fantastic proximity to the beach & a great bakery and ice cream shop. They accommodated us and our dog very well and had everything we need for a great stay. "
United States
Elizabeth C.
$324 nightly
The price is $354
Jan 4 - Jan 5, 2026
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
9.6 out of 10, Exceptional, (26)
"Easy check-in, super clean, amazing location! "
United States
Chantelle V.
$187 nightly
The price is $204
Jan 5 - Jan 6, 2026
Total with taxes and fees
Escape to the Beach! Cozy Condo in downtown OOB.
9.8 out of 10, Exceptional, (122)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
$275 nightly
The price is $300
Jan 4 - Jan 5, 2026
Total with taxes and fees
City Amenities, Casco Bay Sunrises and Natural Beauty
10.0 out of 10, Exceptional, (18)
"Stay was great, as advertised."
United States
Mary Campbell K.
$157 nightly
The price is $171
Jan 4 - Jan 5, 2026
Total with taxes and fees
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
9.6 out of 10, Exceptional, (79)
"Great location. Nice and clean!"
United States
Anonymous traveler
$247 nightly
The price is $269
Jan 4 - Jan 5, 2026
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
10.0 out of 10, Exceptional, (2)
"Our family of 5 had a lovely stay. A lot of parking and lots to do around there. "
United States
Merkara D.
$308 nightly
The price is $336
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sweet, two-bedroom, one-bathroom condo, two short blocks from the beach!
9.8 out of 10, Exceptional, (227)
"The view off the deck was breathtaking "
United States
Raymond
$310 nightly
The price is $338
Jan 2 - Jan 3, 2026
Total with taxes and fees
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.6 out of 10, Exceptional, (24)
"We had an excellent time! Great location"
United States
Erin S.
$449 nightly
The price is $489
Jan 2 - Jan 3, 2026
Total with taxes and fees
Direct ocean views from extra large balcony! Over 1200 square feet!
9.4 out of 10, Exceptional, (3)
"All was great...clean and convenient."
United States
Krista P.
$424 nightly
The price is $462
Jan 4 - Jan 5, 2026
Total with taxes and fees
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Condo in Old Orchard Beach

350 Yards to the beach. Pet friendly!
8.0 out of 10, Very Good, (34)
"Not as nice as some other places we have stayed in OOB, but for the price and closeness to the beach and pier its great. It is right up against the train tracks which wasn’t horrible for us, but could be a significant problem for a light sleeper. "
United States
Kevin S.
$171 nightly
The price is $186
Jan 19 - Jan 20, 2026
Total with taxes and fees
350 Yards to the beach. Pet friendly!
9.6 out of 10, Exceptional, (7)
"The cottage was clean, good location, close to the beach. "
United States
Debra M.
$304 nightly
The price is $331
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming two-bedroom, one-bathroom condo, two short blocks from the beach!
9.6 out of 10, Exceptional, (5)
"This property is wholeheartedly recommended to anyone looking for a memorable Maine getaway. The host was incredibly responsive and provided excellent recommendations for local attractions and dining."
United States
siomaira m.
$304 nightly
The price is $331
Jan 4 - Jan 5, 2026
Total with taxes and fees
Appealing two-bedroom, one-bathroom condo, two short blocks from the beach!
9.8 out of 10, Exceptional, (6)
"Such a great property. It was clean and the location was perfect. We will definitely be back for our next girls trip!"
United States
Kristen O.
$304 nightly
The price is $331
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy 2-bedroom, 1-bathroom condo, two short blocks from the beach!
8.0 out of 10, Very Good, (2)
"The place was cute and conveniently located. A few things could use touching up and better upkeep. Overall, we had a nice stay. "
United States
Katherine m.
$304 nightly
The price is $331
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quaint 2-bedroom, 1-bathroom condo, two short blocks from the beach!
8.0 out of 10, Very Good, (1)
$360 nightly
The price is $392
Jan 4 - Jan 5, 2026
Total with taxes and fees
Relax and unwind in our 4 bedroom beach condo.
9.0 out of 10, Wonderful, (141)
"Great view. Clean pleasant lodgings. "
United States
Mary R.
$265 nightly
The price is $289
Jan 7 - Jan 8, 2026
Total with taxes and fees
Oceanfront Condo! Spectacular Views From Private Large Balcony
8.8 out of 10, Excellent, (37)
"Overall a pleasing stay."
United States
Mallory D.
$412 nightly
The price is $449
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
9.6 out of 10, Exceptional, (21)
"We loved the walkable neighborhood & had a great, comfortable stay!"
United States
Erin R.
$415 nightly
The price is $453
Jan 4 - Jan 5, 2026
Total with taxes and fees
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
9.2 out of 10, Wonderful, (74)
"Location was great. Parking was easy."
United States
Bruce G.
$445 nightly
The price is $485
Jan 4 - Jan 5, 2026
Total with taxes and fees
Elegant condo - walk to Portland's best restaurants & 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

Find out more about Windham

Windham Condo Rentals information

Number of reviews
893
Accommodation
263 Condo Rentals
Lowest Price
$171
Highest Price
$489

Frequently asked questions

Why book your condo in Windham with Expedia?
Use Expedia to find your ideal condo in Windham. On the lookout for someplace luxurious? Try out our filters to search for properties with a 5-star rating. If you have a budget, click on how much you're willing to spend and then check out our fabulous options. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap condos in Windham?
A wonderful way to score cheap condos in Windham is with Expedia's filter tool. Narrow your search results by amenities, budget and star rating to secure awesome rates with only a few clicks.
What is there to do in Windham near my condo?
Once you've unpacked your suitcases, set out and discover the incredible things Windham has for you to experience. Maine Wildlife Park is a top attraction to add to your itinerary.

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