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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

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, (4 reviews)
"Amazing property & so many things to do around the area, we will definitely try to come back!!"
United States
Alyssa
$259 nightly
The price is $282
Nov 29 - Nov 30
Total with taxes and fees
Cozy 1-bedroom cottage in soothing Standish with AC
A two-story house with a gabled roof and a front porch.

2. 3BR Cottage Parking A Peaceful Oasis on Munjoy Hill

3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (2 reviews)
"Super clean and spacious in a walkable area. "
United States
Nell F.
$312 nightly
The price is $341
Nov 30 - Dec 1
Total with taxes and fees
3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
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.

3. 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 house! Wonderful location with so many wonderful touches to make our stay so comfortable. We would definitely stay there again."
United States
Anonymous traveler
$455 nightly
The price is $496
Nov 30 - Dec 1
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
An outdoor patio with picnic tables and chairs, surrounded by trees and a house.

4. 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.
$222 nightly
The price is $242
Nov 24 - Nov 25
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
A backyard with outdoor seating, a fire pit, and a small grill area.

5. Little Miss Cottages 1-4: 1BR by Everrow

Little Miss Cottages 1-4: 1BR by Everrow
Old Orchard Beach
9.2 out of 10, Wonderful, (25 reviews)
"Very good place !! I love it"
United States
Pecheur_Québec
$280 nightly
The price is $305
Nov 10 - Nov 11
Total with taxes and fees
Little Miss Cottages 1-4: 1BR by Everrow
A wooden deck with picnic tables, a blue house, and trees in the background.

6. Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach

Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach
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
$326 nightly
The price is $327
Nov 8 - Nov 9
Total with taxes and fees
Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach
A lakeside house with a dock, a small boathouse, and a flag.

7. 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)
"Great little camp with lake access! Thanks for hosting us :-)"
United States
Anonymous traveler
$278 nightly
The price is $303
Nov 16 - Nov 17
Total with taxes and fees
Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
A backyard with white Adirondack chairs, a small patio table, and blue umbrellas.

8. 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)
"Nice place"
United States
Brad G.
$224 nightly
The price is $244
Nov 8 - Nov 9
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
A two-story house with a front porch, a bench, and a well-maintained lawn.

9. Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1
Old Orchard Beach
10.0 out of 10, Exceptional, (11 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
$224 nightly
The price is $244
Nov 16 - Nov 17
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
A single-story house with a white exterior and dark trim around the windows and door.

10. 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.
$222 nightly
The price is $242
Nov 24 - Nov 25
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
A backyard with white Adirondack chairs, a small patio table, and blue umbrellas.

11. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
9.6 out of 10, Exceptional, (5 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.
$222 nightly
The price is $242
Nov 24 - Nov 25
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from 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.

12. Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach

Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach
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.
$317 nightly
The price is $318
Nov 8 - Nov 9
Total with taxes and fees
Sleeps 5 • 2BR • OOB • 10-min walk to Pier & 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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Learn more about Windham

Outdoor enthusiasts flock to Dundee Park's sandy beach for swimming and picnicking on Pleasant River's shores. Windham's historic district reveals 19th-century charm, while nearby Sebago Lake State Park offers prime fishing and boating.

See all hotels in Windham
A white church with a steeple and red accents, surrounded by autumn trees.

Top reviews in Windham

A multi-story hotel with a covered entrance and a parking area.
Dormir

Dormir

Dormir
Windham

10/10 Excellent

Hotel was very clean and quiet when we arrived. Service was exceptional in every way. All expectations were met.
United States
Kevin
Reviewed August 23, 2019
Dormir

Frequently Asked Questions

How much do cottages in Windham cost?

Cottages in Windham range between $241 and $496 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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