Search Windham Cottages

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Windham cottages

Exterior
Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1
Old Orchard Beach
10.0 out of 10, Exceptional, (3)
"The location was wonderful! The host was so communicative and kind!"
United States
Courtney W.
$179 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
Exterior detail
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok

Renovated 2Bd Cottage 10min walk to Beach. Pets Ok

Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
Old Orchard Beach
7.2 out of 10, Good, (12)
"Was as advertised."
United States
Andrew H.
$176 nightly
The price is $192
Jan 1 - Jan 2, 2026
Total with taxes and fees
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
Exterior
Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
10.0 out of 10, Exceptional, (1)
"Clean, very good communication with the host."
United States
Brandon F.
$269 nightly
The price is $293
Dec 22 - Dec 23
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Exterior
Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool

Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool

Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool
Biddeford
10.0 out of 10, Exceptional, (8)
"It was a great stay. The house is in wonderful condition. The hosts were very helpful and our stay was relaxing and enjoyable. "
United States
Christine K.
$571 nightly
The price is $622
Dec 27 - Dec 28
Total with taxes and fees
Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool
Property grounds
Cheerful 1 bedroom cottage only 50ft from beach

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)
"We loved the area. We loved the cottage feel. We only wished it had bigger fridge and a better cook top. Other then that it was great."
United States
Chris A.
$179 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
Beach nearby
Cozy one bedroom cottage, 50 feet from the beach in OOB.

Cozy one bedroom cottage, 50 feet from the beach in OOB.

Cozy one bedroom cottage, 50 feet from the beach in OOB.
Old Orchard Beach
9.6 out of 10, Exceptional, (4)
"Great location to the beach and the pier! "
United States
Pamela C.
$179 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Exterior
Spacious 2 bedroom cabin, 50ft from the beach

Spacious 2 bedroom cabin, 50ft from the beach

Spacious 2 bedroom cabin, 50ft from the beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1)
"The amenities were perfect and the communication was excellent!"
United States
Dawn C.
$245 nightly
The price is $267
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spacious 2 bedroom cabin, 50ft from the beach
Interior
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

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)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
$195 nightly
The price is $213
Jan 5 - Jan 6, 2026
Total with taxes and fees
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Exterior
The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach

The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach

The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach
Surfside
10.0 out of 10, Exceptional, (3)
"Great place for a family retreat "
United States
joey r.
$657 nightly
The price is $716
Dec 22 - Dec 23
Total with taxes and fees
The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach
Exterior
Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$190 nightly
The price is $207
Jan 4 - Jan 5, 2026
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby
Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$179 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Exterior
Large 2BD cottage 10 min to Pier & Beach Pets ok

Large 2BD cottage 10 min to Pier & Beach Pets ok

Large 2BD cottage 10 min to Pier & Beach Pets ok
Old Orchard Beach
9.0 out of 10, Wonderful, (36)
"Wondeful place to stay while in the area. EASY walk to the beach and all that the boardwalk area has to offer. "
United States
Steven D.
$200 nightly
The price is $218
Dec 30 - Dec 31
Total with taxes and fees
Large 2BD cottage 10 min to Pier & Beach Pets ok
Beach nearby
beautiful 1 bedroom cabin only 50 ft from beach

beautiful 1 bedroom cabin only 50 ft from beach

beautiful 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$179 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
Exterior
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
Brownfield
10.0 out of 10, Exceptional, (3)
"Everything was great for check in, and the amenities and snacks there were a great touch! Came in handy for the couple that forgot to pack their toothbrushes! "
United States
Brian A.
$291 nightly
The price is $317
Jan 6 - Jan 7, 2026
Total with taxes and fees
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"Great room. Courteous staff."
Carmen 1-night trip
Posted 17 hours ago
Clarion Hotel Portland Airport ME

Find out more about Windham

Windham Cottages information

Number of reviews
94
Accommodation
374 Cottages
Lowest Price
$192
Highest Price
$716

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $192 and $716 per night. These retreats offer a chance to reconnect with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Windham?
Enjoy the beauty of nature in one of the 374 cottages available in Windham. To help you find your ideal stay, make use of our handy filters to search for must-have amenities or perks.
Why book your cottage in Windham with Expedia?
Expedia has some superb cottages in Windham, so start planning for an unforgettable stay on nature's doorstep. If you have a fixed budget, click on how much you want to spend and your preferred property star rating. Or, use our handy filters to search for cottages with a pool or a kitchen. We'll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in Windham?
The easiest way to locate cheap cottages in Windham is with Expedia's handy filter tool. Narrow down your search by star rating, amenities and budget to land awesome rates in just a few keystrokes.
What is there to do in Windham near my cottage?
The ideal travel accessory is a well-planned to-do list. Maine Wildlife Park is a top place to kick-start your adventures in Windham.

Explore a world of travel with Expedia