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Oct 17 - Oct 19
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In two months
Dec 5 - Dec 7

Cottages in Windham

Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
Property grounds

Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches

10.0 out of 10, Exceptional, (2)
"Wonderful property with great ocean views! The house was very nice, comfortable and quiet. Found the bed to be very comfortable. Would highly recommend to anyone that is interested in staying in this area."
The price is ￥37,502
￥99,899 total
includes taxes & fees
Nov 2 - Nov 3
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
Cheerful 1 bedroom cottage only 50ft from beach
Exterior

Cheerful 1 bedroom cottage only 50ft from beach

10.0 out of 10, Exceptional, (2)
"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."
The price is ￥19,743
￥34,199 total
includes taxes & fees
Nov 2 - Nov 3
Cheerful 1 bedroom cottage only 50ft from beach
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Exterior detail

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

8.0 out of 10, Very Good, (24)
"Property was just as expected. It was nice for us. Only complaint was the grill was broken and we didn’t realize it until after we went and purchased meats for the grill"
The price is ￥19,131
￥38,203 total
includes taxes & fees
Oct 15 - Oct 16
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Little Miss Cottages - Two Bedroom Cottage
Exterior

Little Miss Cottages - Two Bedroom Cottage

10.0 out of 10, Exceptional, (1)
"Excellent place, so much fun!!!"
The price is ￥21,488
￥45,610 total
includes taxes & fees
Nov 2 - Nov 3
Little Miss Cottages - Two Bedroom Cottage
Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool
Exterior

Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool

10.0 out of 10, Exceptional, (5)
The price is ￥52,917
￥94,100 total
includes taxes & fees
Nov 11 - Nov 12
Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool
Charming 2-bedroom Oceanside Cottage in Old Orchard Beach
Exterior

Charming 2-bedroom Oceanside Cottage in Old Orchard Beach

10.0 out of 10, Exceptional, (2)
"Great stay wonderful local ion"
The price is ￥43,845
￥83,552 total
includes taxes & fees
Oct 24 - Oct 25
Charming 2-bedroom Oceanside Cottage in Old Orchard Beach
The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach
Exterior

The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach

10.0 out of 10, Exceptional, (3)
"Great place for a family retreat "
The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach
Adorable 1 bedroom cabin only 50 ft from beach#1
Exterior

Adorable 1 bedroom cabin only 50 ft from beach#1

10.0 out of 10, Exceptional, (1)
"The location was wonderful! The host was so communicative and kind!"
The price is ￥19,743
￥34,199 total
includes taxes & fees
Nov 2 - Nov 3
Adorable 1 bedroom cabin only 50 ft from beach#1
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Beach nearby

Cozy one bedroom cottage, 50 feet from the beach in OOB.

9.4 out of 10, Exceptional, (3)
"Peaceful and close to the beach, had a great stay "
The price is ￥19,743
￥34,199 total
includes taxes & fees
Nov 2 - Nov 3
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
Private kitchen

Renovated 2Bd Cottage 10min walk to Beach. Pets Ok

7.2 out of 10, Good, (12)
"Super comfortable beds! Small cozy cottage, but with so much to do in town who needs more space?"
The price is ￥21,167
￥40,540 total
includes taxes & fees
Oct 24 - Oct 25
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
beautiful 1 bedroom cabin only 50 ft from beach
Beach nearby

beautiful 1 bedroom cabin only 50 ft from beach

The price is ￥18,213
￥32,197 total
includes taxes & fees
Oct 28 - Oct 29
beautiful 1 bedroom cabin only 50 ft from beach
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

Attractive 1 bedroom cabin only 50 ft from beach

The price is ￥19,743
￥36,034 total
includes taxes & fees
Nov 2 - Nov 3
Attractive 1 bedroom cabin only 50 ft from beach
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

Attractive 1 bedroom cabin only 50 ft from beach

The price is ￥19,743
￥34,199 total
includes taxes & fees
Nov 2 - Nov 3
Attractive 1 bedroom cabin only 50 ft from beach
Spacious 2 bedroom cabin, 50ft from the beach
Exterior

Spacious 2 bedroom cabin, 50ft from the beach

The price is ￥22,804
￥42,373 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 2 bedroom cabin, 50ft from the beach
Little Miss Cottages - Studio
Exterior

Little Miss Cottages - Studio

The price is ￥18,844
￥42,394 total
includes taxes & fees
Oct 13 - Oct 14
Little Miss Cottages - Studio
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.0 out of 10, Wonderful, (36)
"Easy walk into the board walk shopping area ! Private parking and owner was readily available for any issues or concerns....gas station and lobster pound close enough i walked to pick us up dinner....5 lobster fresh cooked $45 and we're still steaming hot by time i walked back to the house"
Large 2BD cottage 10 min to Pier & Beach Pets ok
Little Miss Cottages - One Bedroom Cottage
Exterior

Little Miss Cottages - One Bedroom Cottage

The price is ￥21,488
￥45,443 total
includes taxes & fees
Nov 2 - Nov 3
Little Miss Cottages - One Bedroom Cottage
Little Miss Cottages - Two Bedroom Cottage - 10
Exterior

Little Miss Cottages - Two Bedroom Cottage - 10

The price is ￥24,959
￥49,894 total
includes taxes & fees
Oct 21 - Oct 22
Little Miss Cottages - Two Bedroom Cottage - 10
Little Miss Cottages - 173 House
Outdoor dining

Little Miss Cottages - 173 House

Little Miss Cottages - 173 House
Lakeside cottage with boats, grill, firepit, pet and Kid Friendly
Exterior

Lakeside cottage with boats, grill, firepit, pet and Kid Friendly

9.6 out of 10, Exceptional, (21)
"Our stay at the cabin was wonderful quiet and great weather too host was wonderful and always responded quickly place was perfect and had everything needed to make our stay awesome thank you for a very memorable vacation "
Lakeside cottage with boats, grill, firepit, pet and Kid Friendly
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

Germaine Inn South Portland

Germaine Inn South Portland

10/10 Excellent
"Inside was great, the parking lot had a lot of trash and there was a hypodermic needle among the trash. Again, staff, inside and stay was exceptional. Thank you"
Cynthia 3-night trip
Posted 10 hours ago
Germaine Inn South Portland

Find out more about Windham

Windham Cottages information

Number of reviews
101
Accommodation
457 Cottages
Lowest Price
￥32,197
Highest Price
￥99,899

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between ￥32,197 and ￥99,899 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 457 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.