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

Search Windham Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

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

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Windham cottages

A two-story building with a metal exterior, a door with a cactus and a cow design, and three windows with decorative panels.

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, (2 reviews)
"Amazing property & so many things to do around the area, we will definitely try to come back!!"
United States
Alyssa
$306 nightly
The price is $333
Oct 13 - Oct 14
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, (20 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
$539 nightly
The price is $587
Nov 2 - Nov 3
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A room with a bed, a round wooden table, a ceiling fan, a TV on the wall, and a door leading to another room.

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.
$297 nightly
The price is $301
Nov 3 - Nov 4
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 two-story house with a front porch, a garage, and a well-maintained lawn.

4. 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, (95 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.
$236 nightly
The price is $258
Oct 6 - Oct 7
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.

5. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (24 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.
$291 nightly
The price is $317
Nov 2 - Nov 3
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
A pier extending into calm waters with a building at the end.

6. 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.
$264 nightly
The price is $288
Oct 12 - Oct 13
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
A small, single-story house with a number '20' on the front, a front door, and a small porch with steps leading up to it.

7. 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.
$409 nightly
The price is $446
Oct 18 - Oct 19
Total with taxes and fees
Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
A two-story house with a garage and a covered porch.

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
$297 nightly
The price is $324
Oct 20 - Oct 21
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
A rustic building with a pond, stone pathway, and flower beds.

9. 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.
$264 nightly
The price is $288
Oct 6 - Oct 7
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
A pier with a building on stilts over the beach.

10. 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.
$264 nightly
The price is $288
Oct 6 - Oct 7
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
A two-story house with a front porch, a bench, and a well-maintained lawn.

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.
$264 nightly
The price is $288
Oct 6 - Oct 7
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
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, (4 reviews)
"Great place, dog friendly and very close the beach! Perfect little getaway!"
United States
Jenna M.
$275 nightly
The price is $300
Oct 28 - Oct 29
Total with taxes and fees
Attractive 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.

13. 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
Nov 3 - Nov 4
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.

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

Spacious 2 bedroom cabin, 50ft from the beach
Old Orchard Beach
9.0 out of 10, Wonderful, (4 reviews)
"Clean room, friendly host, a nice part of the beach that you walk out to."
United States
Beverley R.
$363 nightly
The price is $396
Oct 19 - Oct 20
Total with taxes and fees
Spacious 2 bedroom cabin, 50ft from the beach
A lakeside house with a dock, a small boathouse, and a flag.

15. Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table

Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
Brownfield
10.0 out of 10, Exceptional, (6 reviews)
"Everything was great for check in, and the amenities and snacks there were a great touch! Came in handy for the couple that forgot to pack their toothbrushes! "
United States
Brian A.
$317 nightly
The price is $345
Nov 2 - Nov 3
Total with taxes and fees
Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

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

Little Miss Cottages - Two Bedroom Cottage Suite - 9
Old Orchard Beach
6.4 out of 10, (5 reviews)
"First cottage had a foul smell, but host was able to move us to another cottage. They are tiny but have what is needed. Cottage 7 has a definite slant to the floor. Very close to a uncrowded beach."
United States
April H.
$348 nightly
The price is $379
Oct 7 - Oct 8
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

10/10 Excellent
"Clean and well-maintained; helpful staff; right off the highway; easy parking."
Charlie 2-night trip
Posted 7 hours ago
DoubleTree by Hilton Hotel Portland

Find out more about Windham

Windham Cottages information

Number of reviews
184
Accommodation
420 Cottages
Lowest Price
$258
Highest Price
$587

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $258 and $587 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.

Explore a world of travel with Expedia