Search Condo Rentals in Windham

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Windham condo rentals

Cozy, Elegant and Bright 2 bed in the East End

Cozy, Elegant and Bright 2 bed in the East End
Munjoy Hill
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
The price is AED 337
AED 844 total
includes taxes & fees
4 Jan - 5 January 2026
Cozy, Elegant and Bright 2 bed in the East End

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
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.
The price is AED 567
AED 1,299 total
includes taxes & fees
4 Jan - 5 January 2026
Arlie`s Digs! - One Block To Willard Beach!

Escape to the Beach! Cozy Condo in downtown OOB.

Escape to the Beach! Cozy Condo in downtown OOB.
Old Orchard Beach
9.6 out of 10, Exceptional, (26)
"Easy check-in, super clean, amazing location! "
United States
Chantelle V.
The price is AED 331
AED 749 total
includes taxes & fees
5 Jan - 6 January 2026
Escape to the Beach! Cozy Condo in downtown OOB.

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (122)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
The price is AED 529
AED 1,109 total
includes taxes & fees
4 Jan - 5 January 2026
City Amenities, Casco Bay Sunrises and Natural Beauty

Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
Bridgton
10.0 out of 10, Exceptional, (18)
"Stay was great, as advertised."
United States
Mary Campbell K.
The price is AED 501
AED 627 total
includes taxes & fees
5 Jan - 6 January 2026
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (79)
"Great location. Nice and clean!"
United States
Anonymous traveler
The price is AED 401
AED 998 total
includes taxes & fees
4 Jan - 5 January 2026
Walk to Old Port ♦ West End Condo ♦ Parking

Sweet, two-bedroom, one-bathroom condo, two short blocks from the beach!

Sweet, two-bedroom, one-bathroom condo, two short blocks from the beach!
Old Orchard Beach
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.
The price is AED 621
AED 1,233 total
includes taxes & fees
4 Jan - 5 January 2026
Sweet, two-bedroom, one-bathroom condo, two short blocks from the beach!

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Old Orchard Beach
9.8 out of 10, Exceptional, (227)
"The view off the deck was breathtaking "
United States
Raymond
The price is AED 643
AED 1,261 total
includes taxes & fees
2 Jan - 3 January 2026
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Direct ocean views from extra large balcony! Over 1200 square feet!

Direct ocean views from extra large balcony! Over 1200 square feet!
Old Orchard Beach
9.6 out of 10, Exceptional, (24)
"We had an excellent time! Great location"
United States
Erin S.
Direct ocean views from extra large balcony! Over 1200 square feet!

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
West End
9.4 out of 10, Exceptional, (3)
"All was great...clean and convenient."
United States
Krista P.
The price is AED 463
AED 1,709 total
includes taxes & fees
4 Jan - 5 January 2026
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

350 Yards to the beach. Pet friendly!

350 Yards to the beach. Pet friendly!
Old Orchard Beach
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.
The price is AED 257
AED 685 total
includes taxes & fees
19 Jan - 20 January 2026
350 Yards to the beach. Pet friendly!

Charming two-bedroom, one-bathroom condo, two short blocks from the beach!

Charming two-bedroom, one-bathroom condo, two short blocks from the beach!
Old Orchard Beach
9.6 out of 10, Exceptional, (7)
"The cottage was clean, good location, close to the beach. "
United States
Debra M.
The price is AED 621
AED 1,233 total
includes taxes & fees
4 Jan - 5 January 2026
Charming two-bedroom, one-bathroom condo, two short blocks from the beach!

Appealing two-bedroom, one-bathroom condo, two short blocks from the beach!

Appealing two-bedroom, one-bathroom condo, two short blocks from the beach!
Old Orchard 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.
The price is AED 621
AED 1,233 total
includes taxes & fees
4 Jan - 5 January 2026
Appealing two-bedroom, one-bathroom condo, two short blocks from the beach!

Cozy 2-bedroom, 1-bathroom condo, two short blocks from the beach!

Cozy 2-bedroom, 1-bathroom condo, two short blocks from the beach!
Old Orchard 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.
The price is AED 621
AED 1,233 total
includes taxes & fees
4 Jan - 5 January 2026
Cozy 2-bedroom, 1-bathroom condo, two short blocks from the beach!

Quaint 2-bedroom, 1-bathroom condo, two short blocks from the beach!

Quaint 2-bedroom, 1-bathroom condo, two short blocks from the beach!
Old Orchard 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.
The price is AED 621
AED 1,233 total
includes taxes & fees
4 Jan - 5 January 2026
Quaint 2-bedroom, 1-bathroom condo, two short blocks from the beach!

Relax and unwind in our 4 bedroom beach condo.

Relax and unwind in our 4 bedroom beach condo.
Old Orchard Beach
8.0 out of 10, Very Good, (1)
The price is AED 621
AED 1,441 total
includes taxes & fees
4 Jan - 5 January 2026
Relax and unwind in our 4 bedroom beach condo.

Oceanfront Condo! Spectacular Views From Private Large Balcony

Oceanfront Condo! Spectacular Views From Private Large Balcony
Old Orchard Beach
9.0 out of 10, Wonderful, (141)
"Great view. Clean pleasant lodgings. "
United States
Mary R.
The price is AED 514
AED 1,061 total
includes taxes & fees
7 Jan - 8 January 2026
Oceanfront Condo! Spectacular Views From Private Large Balcony

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (37)
"Overall a pleasing stay."
United States
Mallory D.
The price is AED 525
AED 1,648 total
includes taxes & fees
4 Jan - 5 January 2026
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Downtown Portland
9.6 out of 10, Exceptional, (21)
"We loved the walkable neighborhood & had a great, comfortable stay!"
United States
Erin R.
The price is AED 729
AED 1,663 total
includes taxes & fees
4 Jan - 5 January 2026
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (74)
"Location was great. Parking was easy."
United States
Bruce G.
The price is AED 628
AED 1,791 total
includes taxes & fees
4 Jan - 5 January 2026
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windham Hotel Reviews

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.