A white church with a steeple and red accents, surrounded by autumn trees.

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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Windham cottages

Exterior

1. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (16 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
$699 nightly
The price is $762
Sep 2 - Sep 3
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

2. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
$210 nightly
The price is $229
Aug 13 - Aug 14
Total with taxes and fees
Charming Rustic Cottage
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

3. Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs

Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
Old Orchard Beach
7.2 out of 10, Good, (12 reviews)
"Was as advertised."
United States
Andrew H.
$360 nightly
The price is $364
Sep 1 - Sep 2
Total with taxes and fees
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
Exterior

4. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.0 out of 10, Wonderful, (12 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
$397 nightly
The price is $432
Sep 7 - Sep 8
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Exterior

5. Soothing 2-bedroom cottage with Sauna in Old Orchard Beach

Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
Old Orchard Beach
10.0 out of 10, Exceptional, (2 reviews)
"Great place. Would stay again!!"
United States
Jay T.
$410 nightly
The price is $447
Sep 1 - Sep 2
Total with taxes and fees
Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
Exterior

6. Cottage by the Sea #3 by Bayley Vacation Rentals

Cottage by the Sea #3 by Bayley Vacation Rentals
Surfside
8.6 out of 10, Excellent, (4 reviews)
"Great location and cottage! Views of the beach are unbeatable."
United States
Nathan M.
$1,265 nightly
The price is $1,370
Aug 15 - Aug 16
Total with taxes and fees
Cottage by the Sea #3 by Bayley Vacation Rentals
Property grounds

7. Cheerful 1 bedroom cottage only 50ft from beach

Cheerful 1 bedroom cottage only 50ft from beach
Old Orchard Beach
9.6 out of 10, Exceptional, (5 reviews)
"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.
$413 nightly
The price is $450
Sep 8 - Sep 9
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
House (2 Bedrooms) | Interior

8. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
$267 nightly
The price is $291
Aug 25 - Aug 26
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
Interior

9. Large 2BD cottage 10 min to Pier & Beach Sleeps 6<br>- FREE parking<br>- 2 queen beds and futons in the living room<br>- smart TVs<br>- washer and dryer in the unit<br>- picnic table and grill (shared)

Large 2BD cottage 10 min to Pier & Beach Sleeps 6<br>- FREE parking<br>- 2 queen beds and futons in the living room<br>- smart TVs<br>- washer and dryer in the unit<br>- picnic table and grill (shared)
Old Orchard Beach
9.0 out of 10, Wonderful, (41 reviews)
"Clean and convenient. Perfect little place to stay for a spring break in OOB"
United States
Anneliese H.
$392 nightly
The price is $396
Sep 7 - Sep 8
Total with taxes and fees
Large 2BD cottage 10 min to Pier & Beach Sleeps 6<br>- FREE parking<br>- 2 queen beds and futons in the living room<br>- smart TVs<br>- washer and dryer in the unit<br>- picnic table and grill (shared)
Exterior

10. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$456 nightly
The price is $497
Sep 8 - Sep 9
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

11. Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1
Old Orchard Beach
9.8 out of 10, Exceptional, (8 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
$401 nightly
The price is $437
Sep 8 - Sep 9
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
Beach nearby

12. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
10.0 out of 10, Exceptional, (3 reviews)
"Great place! Loved being on the end so we only had one neighbor. No crazy list of things to do at check out was much appreciated."
United States
Mandy H.
$489 nightly
The price is $533
Sep 8 - Sep 9
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

13. 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, (5 reviews)
"Great location to the beach and the pier! "
United States
Pamela C.
$542 nightly
The price is $591
Aug 14 - Aug 15
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Great location. Beautiful historic property. I felt updated and modernized. Definitely recommend."
susan 1-night trip
Posted 6 hours ago
Portland Regency Hotel & Spa

Find out more about Windham

Windham Cottages information

Number of reviews
108
Accommodation
427 Cottages
Lowest Price
$229
Highest Price
$1,370

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $229 and $1,370 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 427 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.

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