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

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Our top choices for Windham cottages

A shower area with stone tiles and a wooden beam ceiling.

1. Cozy 1-bedroom cottage in soothing Standish with AC

Cozy 1-bedroom cottage in soothing Standish with AC
Standish
$324 nightly
The price is $353
Sep 20 - Sep 21
Total with taxes and fees
Cozy 1-bedroom cottage in soothing Standish with AC
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.

2. 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, (18 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
$543 nightly
The price is $592
Oct 6 - Oct 7
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A wooden deck with wicker furniture and a view of boats on the water.

3. 'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (23 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
$570 nightly
The price is $621
Sep 30 - Oct 1
Total with taxes and fees
'Osprey Cottage' South Freeport Home on Casco Bay!
A wooden deck with wicker furniture and a view of boats on the water.

4. 'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
$579 nightly
The price is $614
Sep 30 - Oct 1
Total with taxes and fees
'osprey Cottage' South Freeport Home on Casco Bay!
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.

5. 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.
Cottages by the Sea #1 by Bayley Vacation Rentals
A two-story house with a front porch, a garage, and a well-maintained lawn.

6. 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, (90 reviews)
"Great, pet-friendly spot! Walkable to the beach, places to eat, etc. Loved the space (indoor and outdoor) to spread out a bit."
United States
Blake S.
$343 nightly
The price is $374
Sep 21 - Sep 22
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.

7. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.0 out of 10, Wonderful, (18 reviews)
"It was very clean and it’s pet friendly. The host went above and beyond and was truly friendly while doing so. A great location and quiet at this time of year. The bed was very comfortable. The shower nice and hot. I would rent that seaside shanty again. "
United States
Lynne B.
$334 nightly
The price is $364
Sep 8 - Sep 9
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
A single-story house with a covered porch, a front door, and a window.

8. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
$176 nightly
The price is $192
Sep 12 - Sep 13
Total with taxes and fees
Charming Rustic Cottage
A small house with a wooden deck and a porch.

9. •Tranquil 2BR Summer Home•Steps to Private Beach•

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
10.0 out of 10, Exceptional, (1 review)
$540 nightly
The price is $589
Oct 1 - Oct 2
Total with taxes and fees
•Tranquil 2BR Summer Home•Steps to Private Beach•
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.
$295 nightly
The price is $298
Sep 29 - Sep 30
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 small house with a blue door, a deck with outdoor furniture, and a 'Welcome' sign.

11. Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful place!"
United States
Louise P.
$766 nightly
The price is $828
Sep 23 - Sep 24
Total with taxes and fees
Nautical View
A wooden pier with multiple pillars extending into the water.

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.
$288 nightly
The price is $314
Sep 14 - Sep 15
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
A rustic building with a pond, stone pathway, and flower beds.

13. 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.
$288 nightly
The price is $314
Sep 15 - Sep 16
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
A two-story house with a garage and a covered porch.

14. 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 two-story house with a front porch, a bench, and a well-maintained lawn.

15. 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, (9 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
$288 nightly
The price is $314
Sep 14 - Sep 15
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
A room with a ceiling fan, a dining table with chairs, a sofa, and a window with blinds.

16. 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, (45 reviews)
"Clean and convenient. Perfect little place to stay for a spring break in OOB"
United States
Anneliese H.
$336 nightly
The price is $340
Sep 29 - Sep 30
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 pier extending into calm waters with a building at the end.

17. 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
9.8 out of 10, Exceptional, (6 reviews)
"Great location to the beach and the pier! "
United States
Pamela C.
$288 nightly
The price is $314
Sep 21 - Sep 22
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
An aerial view of a residential area with numbered houses, a central patio with outdoor furniture, and surrounding greenery.

18. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$289 nightly
The price is $315
Sep 16 - Sep 17
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
A beach with people, a pier, and an American flag.

19. 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
$305 nightly
The price is $308
Oct 7 - Oct 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 white wooden house with a white picket fence, a small porch, and a window with shutters.

20. 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.
$372 nightly
The price is $405
Sep 8 - Sep 9
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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

8/10 Good
"We love the Clarion for its handy location and free, non-valet parking. At the end of a busy summer it IS looking a bit battered--signage is faded, hall carpets are worn/dirty, and the rooms have some dings and scuffs. Still: good overall. Hope it gets a touch up on the off season."
Rebecca 1-night trip
Posted 1 hour ago
Clarion Hotel Portland Airport ME

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Windham Cottages information

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Frequently asked questions

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