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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Windham cottages

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

Cozy 1-bedroom cottage in soothing Standish with AC
Standish
10.0 out of 10, Exceptional, (1 review)
"Amazing property & so many things to do around the area, we will definitely try to come back!!"
United States
Alyssa
$326 nightly
The price is $355
Sep 20 - Sep 21
Total with taxes and fees
Cozy 1-bedroom cottage in soothing Standish with AC
Exterior

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, (19 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
$527 nightly
The price is $575
Sep 28 - Sep 29
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Outdoor dining

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.
$593 nightly
The price is $646
Sep 24 - Sep 25
Total with taxes and fees
'Osprey Cottage' South Freeport Home on Casco Bay!
Cottage (2 Bedrooms) | Interior

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 24 - Sep 25
Total with taxes and fees
'osprey Cottage' South Freeport Home on Casco Bay!
Outdoor dining

5. Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed

Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed
SEBAGO
10.0 out of 10, Exceptional, (1 review)
"Absolutely beautiful location. Quiet area on the lake and great sunrises. Will definitely go back."
United States
Christian R.
$787 nightly
The price is $858
Oct 13 - Oct 14
Total with taxes and fees
Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed
Exterior

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, (91 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.
$254 nightly
The price is $277
Oct 14 - Oct 15
Total with taxes and fees
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

7. Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful place!"
United States
Louise P.
$708 nightly
The price is $764
Sep 23 - Sep 24
Total with taxes and fees
Nautical View
Exterior

8. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (21 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.
$338 nightly
The price is $368
Sep 21 - Sep 22
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Exterior

9. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
$155 nightly
The price is $169
Sep 25 - Sep 26
Total with taxes and fees
Charming Rustic Cottage
Beach nearby

10. 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.
$289 nightly
The price is $315
Sep 20 - Sep 21
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, (9 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
$289 nightly
The price is $315
Sep 20 - Sep 21
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
Property grounds

12. 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 23 - Sep 24
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft 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
9.8 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.
House (2 Bedrooms) | Interior

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
Beach nearby

15. 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.
$283 nightly
The price is $308
Sep 24 - Sep 25
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
Exterior

16. 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 20 - Sep 21
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

17. 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.
$352 nightly
The price is $384
Sep 23 - Sep 24
Total with taxes and fees
Spacious 2 bedroom cabin, 50ft from the beach
Exterior

18. 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.
$413 nightly
The price is $450
Oct 13 - Oct 14
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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"Nice clean place. Easy walk to the Thompson’s Point music venue."
Paul 1-night trip
Posted 1 hour ago
Clarion Hotel Portland Airport ME

Find out more about Windham

Windham Cottages information

Number of reviews
183
Accommodation
420 Cottages
Lowest Price
$169
Highest Price
$858

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $169 and $858 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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