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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Windham cottages

Exterior

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, (15 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
The price is ￥72,195
￥118,515 total
includes taxes & fees
Aug 18 - Aug 19
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

Cottages By The Sea #2 by Bayley Vacation Rentals

Cottages By The Sea #2 by Bayley Vacation Rentals
Surfside
10.0 out of 10, Exceptional, (2 reviews)
"Perfect little getaway."
United States
Tish L.
The price is ￥50,286
￥151,740 total
includes taxes & fees
Aug 1 - Aug 2
Cottages By The Sea #2 by Bayley Vacation Rentals
Exterior

Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.0 out of 10, Wonderful, (9 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
The price is ￥37,687
￥77,150 total
includes taxes & fees
Jul 26 - Jul 27
Little Miss Cottages - One Bedroom Cottage
Beach nearby

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
9.6 out of 10, Exceptional, (4 reviews)
"Great location to the beach and the pier! "
United States
Pamela C.
The price is ￥54,234
￥82,511 total
includes taxes & fees
Jul 26 - Jul 27
Cozy one bedroom cottage, 50 feet from the beach in OOB.
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

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.
The price is ￥36,985
￥70,667 total
includes taxes & fees
Aug 25 - Aug 26
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
Exterior

Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
The price is ￥31,452
￥38,212 total
includes taxes & fees
Aug 24 - Aug 25
Charming Rustic Cottage
Exterior

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, (81 reviews)
"Perfect getaway cottage for my husband & me & our 2 small dogs. And a fenced-in yard!"
United States
Margaret K.
The price is ￥36,125
￥60,270 total
includes taxes & fees
Jul 26 - Jul 27
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

Cottages by the Sea #1 by Bayley Vacation Rentals

Cottages by the Sea #1 by Bayley Vacation Rentals
Surfside
9.8 out of 10, Exceptional, (8 reviews)
"Clean place, had everything we needed, and can’t beat the location. Will definitely be back."
United States
Matthew J.
The price is ￥72,815
￥207,183 total
includes taxes & fees
Aug 1 - Aug 2
Cottages by the Sea #1 by Bayley Vacation Rentals
Exterior

Cottage by the Sea #3 by Bayley Vacation Rentals

Cottage by the Sea #3 by Bayley Vacation Rentals
Surfside
8.6 out of 10, Excellent, (4 reviews)
"Great location and cottage! Views of the beach are unbeatable."
United States
Nathan M.
The price is ￥82,548
￥239,257 total
includes taxes & fees
Aug 15 - Aug 16
Cottage by the Sea #3 by Bayley Vacation Rentals
Exterior

Little Miss Cottages - Two Bedroom Cottage Suite - 9

Little Miss Cottages - Two Bedroom Cottage Suite - 9
Old Orchard Beach
5.0 out of 10, (2 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 ￥46,540
￥93,591 total
includes taxes & fees
Jul 28 - Jul 29
Little Miss Cottages - Two Bedroom Cottage Suite - 9
Exterior

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, (6 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
The price is ￥61,109
￥91,431 total
includes taxes & fees
Jul 29 - Jul 30
Adorable 1 bedroom cabin only 50 ft from beach#1
Exterior

Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
The price is ￥65,368
￥96,609 total
includes taxes & fees
Jul 27 - Jul 28
Attractive 1 bedroom cabin only 50 ft from beach
Property grounds

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 ￥73,560
￥106,074 total
includes taxes & fees
Aug 5 - Aug 6
Cheerful 1 bedroom cottage only 50ft from beach
Beach nearby

beautiful 1 bedroom cabin only 50 ft from beach

beautiful 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
The price is ￥65,368
￥96,609 total
includes taxes & fees
Jul 27 - Jul 28
beautiful 1 bedroom cabin only 50 ft from beach
Beach nearby

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.
The price is ￥76,181
￥110,181 total
includes taxes & fees
Aug 24 - Aug 25
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

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.
The price is ￥86,677
￥128,411 total
includes taxes & fees
Aug 6 - Aug 7
Spacious 2 bedroom cabin, 50ft from the beach
Beach

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
8.0 out of 10, Very Good, (24 reviews)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is ￥46,279
￥81,929 total
includes taxes & fees
Aug 19 - Aug 20
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.
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Top Windham Hotel Reviews

Waves Oceanfront Resort

Waves Oceanfront Resort

10/10 Excellent
"Nous avions accès à 4 piscines, c’est exceptionnel."
Steven 2-night trip
Posted 1 hour ago
Waves Oceanfront Resort

Find out more about Windham

Windham Cottages information

Number of reviews
167
Accommodation
420 Cottages
Lowest Price
￥38,212
Highest Price
￥239,257

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between ￥38,212 and ￥239,257 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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