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

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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.
$698 nightly
The price is $761
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
$208 nightly
The price is $227
Aug 23 - Aug 24
Total with taxes and fees
Charming Rustic Cottage
Exterior

3. Cottages by the Sea #1 by Bayley Vacation Rentals

Cottages by the Sea #1 by Bayley Vacation Rentals
Surfside
9.8 out of 10, Exceptional, (9 reviews)
"Clean place, had everything we needed, and can’t beat the location. Will definitely be back."
United States
Matthew J.
$896 nightly
The price is $969
Sep 7 - Sep 8
Total with taxes and fees
Cottages by the Sea #1 by Bayley Vacation Rentals
Exterior

4. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (15 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
$383 nightly
The price is $417
Sep 7 - Sep 8
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Exterior

5. Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful place!"
United States
Louise P.
$897 nightly
The price is $970
Sep 4 - Sep 5
Total with taxes and fees
Nautical View
Interior

6. 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, (43 reviews)
"Clean and convenient. Perfect little place to stay for a spring break in OOB"
United States
Anneliese H.
$385 nightly
The price is $390
Sep 8 - Sep 9
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

7. 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.
$425 nightly
The price is $463
Sep 7 - Sep 8
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
Beach

8. Updated 2 BD cottage. 10 min walk to Pier & Beach<br>- FREE parking<br>- 2 Queen beds and a futon<br>- Fast fiber Wifi<br>- ACs<br>- 2 smart TVs

Updated 2 BD cottage. 10 min walk to Pier & Beach<br>- FREE parking<br>- 2 Queen beds and a futon<br>- Fast fiber Wifi<br>- ACs<br>- 2 smart TVs
Old Orchard Beach
8.0 out of 10, Very Good, (24 reviews)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
$356 nightly
The price is $360
Sep 8 - Sep 9
Total with taxes and fees
Updated 2 BD cottage. 10 min walk to Pier & Beach<br>- FREE parking<br>- 2 Queen beds and a futon<br>- Fast fiber Wifi<br>- ACs<br>- 2 smart TVs
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

9. 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.
$372 nightly
The price is $377
Sep 14 - Sep 15
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
Beach nearby

10. 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.
$428 nightly
The price is $467
Sep 10 - Sep 11
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Property grounds

11. 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.
$425 nightly
The price is $463
Sep 7 - Sep 8
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
Exterior

12. Spacious 2 bedroom cabin, 50ft from the beach

Spacious 2 bedroom cabin, 50ft from the beach
Old Orchard Beach
8.8 out of 10, Excellent, (3 reviews)
"Clean room, friendly host, a nice part of the beach that you walk out to."
United States
Beverley R.
$483 nightly
The price is $526
Sep 8 - Sep 9
Total with taxes and fees
Spacious 2 bedroom cabin, 50ft from the beach
Beach nearby

13. 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.
$425 nightly
The price is $463
Sep 7 - Sep 8
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

14. beautiful 1 bedroom cabin only 50 ft from beach

beautiful 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Being so close to the water was great. Place was a little smaller than we typically get but sufficient and was very clean. The owner was great to communicate with and quick to respond to questions. We particularly liked the shaded patio area in front."
United States
Allan S.
$425 nightly
The price is $463
Sep 7 - Sep 8
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
Exterior

15. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$448 nightly
The price is $488
Sep 15 - Sep 16
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

16. Little Miss Cottages - Two Bedroom Cottage Suite - 9

Little Miss Cottages - Two Bedroom Cottage Suite - 9
Old Orchard Beach
5.4 out of 10, (3 reviews)
"WiFi and tv was spotty on a good day and non existent towards the end of our stay. If we were to go again I wouldn’t want to stay in suite 9. Some of the other cottages were a little more secluded and had a deck."
United States
Ralph B.
$468 nightly
The price is $511
Aug 30 - Aug 31
Total with taxes and fees
Little Miss Cottages - Two Bedroom Cottage Suite - 9
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

The Westin Portland Harborview

The Westin Portland Harborview

8/10 Good
"Convient location is why I chose it. A 15 minute walk to downtown wharf with all it’s charming restaurants & bars. No need to drive. Room OK. Not 5-Star. All of Portland is Manhattan prices. Parked in public garage adjoining hotel. Green sign. Hotel charged me $38 for the one night of parking. Breakfast was included but not allowed dishes that include lobster.😀"
Brian 1-night trip
Posted 4 hours ago
The Westin Portland Harborview

Find out more about Windham

Windham Cottages information

Number of reviews
152
Accommodation
420 Cottages
Lowest Price
$227
Highest Price
$970

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $227 and $970 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 420 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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