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

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In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Windham cottages

A two-story house with a white exterior and a black base. There is a white staircase leading to the front door, surrounded by lush greenery and flowering plants.

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, (17 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
$681 nightly
The price is $742
Sep 2 - Sep 3
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A beachfront property with multiple buildings, including a cottage-style house and a larger building with a balcony. There are several white lounge chairs arranged on the sandy beach in front of the buildings.

2. 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.
$888 nightly
The price is $960
Sep 7 - Sep 8
Total with taxes and fees
Cottages by the Sea #1 by Bayley Vacation Rentals
A two-story house with a front porch, a garage, and a well-maintained lawn.

3. Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Old Orchard Beach
9.8 out of 10, Exceptional, (87 reviews)
"Perfect getaway cottage for my husband & me & our 2 small dogs. And a fenced-in yard!"
United States
Margaret K.
$322 nightly
The price is $351
Sep 1 - Sep 2
Total with taxes and fees
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

4. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (17 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
$340 nightly
The price is $371
Sep 1 - Sep 2
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
A small house with a blue door, a deck with outdoor furniture, and a 'Welcome' sign.

5. Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful place!"
United States
Louise P.
$823 nightly
The price is $889
Sep 4 - Sep 5
Total with taxes and fees
Nautical View
A room with a ceiling fan, a dining table with chairs, a sofa, and a window with blinds.

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.
$324 nightly
The price is $327
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)
A rustic building with a pond, stone pathway, and flower beds.

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.
$313 nightly
The price is $341
Sep 1 - Sep 2
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach

8. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
$233 nightly
The price is $254
Sep 6 - Sep 7
Total with taxes and fees
Charming Rustic Cottage
A two-story house with a garage and a covered porch.

9. 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
$249 nightly
The price is $271
Sep 23 - Sep 24
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
A room with a bed, a round wooden table, a ceiling fan, a TV on the wall, and a door leading to another room.

10. 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.
$285 nightly
The price is $288
Sep 22 - Sep 23
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
A wooden pier with multiple pillars extending into the water.

11. 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.
$313 nightly
The price is $341
Aug 31 - Sep 1
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
A two-story house with a front porch, a bench, and a well-maintained lawn.

12. 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.
$313 nightly
The price is $341
Aug 31 - Sep 1
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
A beach with people, a pier, and an American flag.

13. 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
8.2 out of 10, Very Good, (26 reviews)
"Even though the property was small it was spacious for two people especially my husband and I we had an awesome awesome week there the host was unbelievably kind the woman Kathy that clean the unit was exceptional and very very nice the neighborhood was peaceful and it was very convenient to the pier and all the shops definitely will be staying there from now on every year it was awesome"
United States
Catherine
$301 nightly
The price is $305
Sep 7 - Sep 8
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
A pier extending into calm waters with a building at the end.

14. 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.
$313 nightly
The price is $341
Aug 31 - Sep 1
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

15. 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.
$395 nightly
The price is $430
Sep 1 - Sep 2
Total with taxes and fees
Little Miss Cottages - Two Bedroom Cottage Suite - 9
A pier with a building on stilts over the beach.

16. 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.
$313 nightly
The price is $341
Aug 31 - Sep 1
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
An aerial view of a residential area with numbered houses, a central patio with outdoor furniture, and surrounding greenery.

17. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$313 nightly
The price is $341
Aug 31 - Sep 1
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
A white wooden house with a white picket fence, a small porch, and a window with shutters.

18. 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.
$447 nightly
The price is $487
Sep 29 - Sep 30
Total with taxes and fees
Spacious 2 bedroom cabin, 50ft from the beach
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"Helpful staff and the shuttle to/from airport and back and forth from downtown was really great."
DeeDee 4-night trip
Posted 2 hours ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Windham

Windham Cottages information

Number of reviews
Accommodation
420 Cottages
Lowest Price
$271
Highest Price
$271

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $271 and $271 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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