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

Search Windham Cottages

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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
The price is £228
includes taxes & fees
21 Oct - 22 Oct
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, (22 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is £502
includes taxes & fees
25 Oct - 26 Oct
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)
"Super comfortable beds! Small cozy cottage, but with so much to do in town who needs more space?"
United States
John G.
The price is £225
includes taxes & fees
3 Nov - 4 Nov
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, (96 reviews)
"Very clean and my dog loved the fenced in yard"
United States
Jackie S.
The price is £210
includes taxes & fees
14 Oct - 15 Oct
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
A pier with a building on stilts over the beach.

5. 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.
The price is £212
includes taxes & fees
14 Oct - 15 Oct
beautiful 1 bedroom cabin only 50 ft from beach
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

6. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (25 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.
The price is £243
includes taxes & fees
14 Oct - 15 Oct
Little Miss Cottages - One Bedroom Cottage
A wooden pier with multiple pillars extending into the water.

7. 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.
The price is £221
includes taxes & fees
14 Oct - 15 Oct
Attractive 1 bedroom cabin only 50 ft from beach
A rustic building with a pond, stone pathway, and flower beds.

8. 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.
The price is £221
includes taxes & fees
14 Oct - 15 Oct
Cheerful 1 bedroom cottage only 50ft from beach
A pier extending into calm waters with a building at the end.

9. 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.
The price is £221
includes taxes & fees
28 Oct - 29 Oct
Cozy one bedroom cottage, 50 feet from the beach in OOB.
A two-story house with a garage and a covered porch.

10. 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
The price is £244
includes taxes & fees
20 Oct - 21 Oct
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.

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.
The price is £221
includes taxes & fees
14 Oct - 15 Oct
Adorable 1 bedroom cabin only 50 ft from beach#1
An aerial view of a residential area with numbered houses, a central patio with outdoor furniture, and surrounding greenery.

12. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
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.

13. 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.
The price is £258
includes taxes & fees
1 Nov - 2 Nov
Spacious 2 bedroom cabin, 50ft from the beach
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

14. 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.
The price is £290
includes taxes & fees
14 Oct - 15 Oct
Little Miss Cottages - Two Bedroom Cottage Suite - 9
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.
The price is £252
includes taxes & fees
2 Nov - 3 Nov
Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
A beach with people, a pier, and an American flag.

16. 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, (28 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
The price is £269
includes taxes & fees
12 Nov - 13 Nov
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
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

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

10/10 Excellent
"No complaints - friendly staff and good property for a one night stay!"
Sam 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Find out more about Windham

Windham Cottages information

Number of reviews
118
Accommodation
430 Cottages
Lowest Price
£210
Highest Price
£502

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between £210 and £502 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 430 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