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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 269 Condo Rentals in Windham with updated reviews, rates, and availability.

Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (105)
"Lovely, clean & great location!"
Gorgeous ocean-front home with stunning beach views
Cozy, Elegant and Bright 2 bed in the East End
Fridge, microwave, oven, stovetop

Cozy, Elegant and Bright 2 bed in the East End

9.8 out of 10, Exceptional, (36)
"Excellent stay and location"
The price is $361
includes taxes & fees
$331 per night
May 2 - May 3
Cozy, Elegant and Bright 2 bed in the East End
Oceanfront Condo! Spectacular Views From Private Large Balcony
On the beach

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (122)
"Great location! If you are looking for quiet time during the evening hours this isn’t the place for you as The Brunswick restaurant is directly below. If you like music and a great view, it’s an amazing spot! "
The price is $305
includes taxes & fees
$280 per night
May 5 - May 6
Oceanfront Condo! Spectacular Views From Private Large Balcony
City Amenities, Casco Bay Sunrises and Natural Beauty
Interior

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (105)
"Very comfortable, close to shopping and restaurants, clean, easily accessible"
The price is $269
includes taxes & fees
$247 per night
May 4 - May 5
City Amenities, Casco Bay Sunrises and Natural Beauty
Direct ocean views from extra large balcony! Over 1200 square feet!
On the beach

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

10.0 out of 10, Exceptional, (12)
"Great condo at a great location."
The price is $523
includes taxes & fees
$480 per night
May 1 - May 2
Direct ocean views from extra large balcony! Over 1200 square feet!
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Beach nearby, beach towels

Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

8.2 out of 10, Very Good, (34)
"Is a nice little condo that I we enjoy but next time I should get a 3 bedroom place"
The price is $373
includes taxes & fees
$342 per night
May 18 - May 19
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Parking!
TV, stereo

“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Parking!

10.0 out of 10, Exceptional, (175)
"Beautiful space with an incredible view. Can’t beat the location. Easy and straight forward directions, clean, and comfy. "
The price is $770
includes taxes & fees
$706 per night
May 29 - May 30
“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Parking!
Sky Deck Penthouse Condo, Walk to Beach and Pier
Point of interest

Sky Deck Penthouse Condo, Walk to Beach and Pier

9.8 out of 10, Exceptional, (24)
"Really enjoyed our stay. The property was spacious, clean and modern and convenient to the beach and amusements. We definitely plan to stay here again next year!"
Sky Deck Penthouse Condo, Walk to Beach and Pier
DriftwoodHouse @ Ocean Landing Condominiums 1 minute walk to the beach Sleeps 8
Fridge, microwave, oven, stovetop

DriftwoodHouse @ Ocean Landing Condominiums 1 minute walk to the beach Sleeps 8

10.0 out of 10, Exceptional, (14)
"Beautiful place, very clean and minutes from the beach and pier. We had a wonderful time and i highly recommend this."
DriftwoodHouse @ Ocean Landing Condominiums 1 minute walk to the beach Sleeps 8
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
Miscellaneous

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

10.0 out of 10, Exceptional, (7)
"Our stay was amazing.. close to town, very comfortable and met all of our needs.. would definitely stay there again!"
The price is $169
includes taxes & fees
$155 per night
May 5 - May 6
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
Eastbayside/Munjoy - Charming Downtown Escape
3 bedrooms, iron/ironing board, WiFi, bed sheets

Eastbayside/Munjoy - Charming Downtown Escape

10.0 out of 10, Exceptional, (22)
"Great location and space "
Eastbayside/Munjoy - Charming Downtown Escape
Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style
Fridge, microwave, oven, stovetop

Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style

9.8 out of 10, Exceptional, (37)
"The en-suite bedroom/bathrooms worked perfectly for us."
Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style
Garden Deck on 1st floor - Close to Beach & Pier. Easy Access.
Point of interest

Garden Deck on 1st floor - Close to Beach & Pier. Easy Access.

10.0 out of 10, Exceptional, (12)
"We had an amazing time. Property was clean and comfortable. We loved this dog friendly location and hope to visit again next year!"
Garden Deck on 1st floor - Close to Beach & Pier. Easy Access.
Back Cove - Sunny 2nd Floor Condo
Terrace/patio

Back Cove - Sunny 2nd Floor Condo

10.0 out of 10, Exceptional, (4)
"The property was as listed, very clean, very comfortable and a wonderful, safe location. "
The price is $294
includes taxes & fees
$270 per night
May 1 - May 2
Back Cove - Sunny 2nd Floor Condo
Oceanfront Condo – Walk to Pier & beach out your front door!
On the beach, sun loungers

Oceanfront Condo – Walk to Pier & beach out your front door!

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had such a great stay! The location honestly couldn’t be better - right on the beach and just a short walk to the Pier! The condo itself was clean and comfortable. The loft was perfect for our kids. They loved having their own space and said the beds were comfortable. It had everything we needed and we'll be booking again for next year! "
Oceanfront Condo – Walk to Pier & beach out your front door!
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Interior

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

9.8 out of 10, Exceptional, (202)
"Great codo unit, very close to everything "
The price is $400
includes taxes & fees
$367 per night
May 4 - May 5
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Gorgeously renovated, 2-condo property in the West End - walk everywhere
Fridge, microwave, oven, stovetop

Gorgeously renovated, 2-condo property in the West End - walk everywhere

9.6 out of 10, Exceptional, (8)
"We traveled with 4 couples so this combo unit was perfect. The location was walkable to everything wanted to get to and Portland was a great launching spot for day trips to check out the neighboring towns."
Gorgeously renovated, 2-condo property in the West End - walk everywhere
Sun Deck It's All Here! Beach, Pier, Bright & FUN
Beach nearby

Sun Deck It's All Here! Beach, Pier, Bright & FUN

9.4 out of 10, Exceptional, (25)
"It was a beautiful condo we just loved everything from the comfortable beds to the great location to the beach. "
Sun Deck It's All Here! Beach, Pier, Bright & FUN
Cozy Newly Renovated 2-bedroom Condo By The Beach
Miscellaneous

Cozy Newly Renovated 2-bedroom Condo By The Beach

Cozy Newly Renovated 2-bedroom Condo By The Beach
Walk to Old Port ♦ West End Condo ♦ Parking
Microwave, oven, coffee/tea maker, cookware/dishes/utensils

Walk to Old Port ♦ West End Condo ♦ Parking

9.8 out of 10, Exceptional, (73)
"Everything was amazing!!"
The price is $272
includes taxes & fees
$249 per night
May 5 - May 6
Walk to Old Port ♦ West End Condo ♦ Parking
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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Other property types in Windham

WATERFRONT ON PETTENGILL POND
Smart TV

WATERFRONT ON PETTENGILL POND

WATERFRONT ON PETTENGILL POND
The Weldon Hotel
Deluxe Suite, 2 Bedrooms | Private kitchen | Full-size fridge, microwave, oven, stovetop

The Weldon Hotel

4.0 star property
9.8 out of 10, Exceptional, (56)
"Great hotel"
The price is $311
includes taxes & fees
$292 per night
May 11 - May 12
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (105)
"Lovely, clean & great location!"
Gorgeous ocean-front home with stunning beach views
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.

Frequently asked questions

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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.