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
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Windham cottages

House (2 Bedrooms) | Interior

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
1 Mi to Maine Street! Mcm-style Home in Brunswick
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, (76 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
The price is £304
includes taxes & fees
15 Jul - 16 Jul
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

•Tranquil 2BR Summer Home•Steps to Private Beach•

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
The price is £400
includes taxes & fees
14 Jul - 15 Jul
•Tranquil 2BR Summer Home•Steps to Private Beach•
Outdoor dining

'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (22 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
The price is £489
includes taxes & fees
19 Jul - 20 Jul
'Osprey Cottage' South Freeport Home on Casco Bay!
Exterior

The Outlet House, Comfortable Cottage

The Outlet House, Comfortable Cottage
Freeport
9.8 out of 10, Exceptional, (58 reviews)
"Awesome place. Thank you for the hospitality!"
United States
Nick F.
The Outlet House, Comfortable Cottage
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Renovated 2Bd Cottage 10min walk to Beach.

Renovated 2Bd Cottage 10min walk to Beach.
Old Orchard Beach
7.2 out of 10, Good, (12 reviews)
"Was as advertised."
United States
Andrew H.
The price is £248
includes taxes & fees
8 Jul - 9 Jul
Renovated 2Bd Cottage 10min walk to Beach.
Exterior

Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.0 out of 10, Wonderful, (7 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
The price is £330
includes taxes & fees
8 Jul - 9 Jul
Little Miss Cottages - One Bedroom Cottage
Exterior

Cottages by the Sea #1 by Bayley Vacation Rentals

Cottages by the Sea #1 by Bayley Vacation Rentals
Surfside
10.0 out of 10, Exceptional, (7 reviews)
"Clean place, had everything we needed, and can’t beat the location. Will definitely be back."
United States
Matthew J.
The price is £868
includes taxes & fees
13 Jul - 14 Jul
Cottages by the Sea #1 by Bayley Vacation Rentals
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 £484
includes taxes & fees
6 Aug - 7 Aug
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Interior

Large 2BD cottage 10 min to Pier & Beach Sleeps 6

Large 2BD cottage 10 min to Pier & Beach Sleeps 6
Old Orchard Beach
9.0 out of 10, Wonderful, (40 reviews)
"The location and the space is great!!"
United States
Anonymous traveller
The price is £361
includes taxes & fees
13 Jul - 14 Jul
Large 2BD cottage 10 min to Pier & Beach Sleeps 6
Cottage (2 Bedrooms) | Front of property

'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
The price is £458
includes taxes & fees
19 Jul - 20 Jul
'osprey Cottage' South Freeport Home on Casco Bay!
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 £747
includes taxes & fees
24 Jul - 25 Jul
Cottages By The Sea #2 by Bayley Vacation Rentals
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 £395
includes taxes & fees
8 Jul - 9 Jul
Cheerful 1 bedroom cottage only 50ft 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, (2 reviews)
"It was very close to the beach but I would not call it beach view. Having said that it was only a very short walk, 5 minutes. The cabin was perfect for two people and two mid sized dogs. Very clean and well supplied. Will most certainly book again."
United States
Nichole B.
The price is £395
includes taxes & fees
8 Jul - 9 Jul
Attractive 1 bedroom cabin only 50 ft from beach
Beach

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

Updated 2 BD cottage. 10 min walk to Pier & Beach
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 £273
includes taxes & fees
8 Jul - 9 Jul
Updated 2 BD cottage. 10 min walk to Pier & Beach
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 £533
includes taxes & fees
23 Jul - 24 Jul
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 £460
includes taxes & fees
6 Aug - 7 Aug
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)
"The amenities were perfect and the communication was excellent!"
United States
Dawn C.
The price is £639
includes taxes & fees
6 Aug - 7 Aug
Spacious 2 bedroom cabin, 50ft from the beach
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 £347
includes taxes & fees
8 Jul - 9 Jul
Little Miss Cottages - Two Bedroom Cottage Suite - 9
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 £470
includes taxes & fees
10 Jul - 11 Jul
beautiful 1 bedroom cabin only 50 ft from 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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Top Windham Hotel Reviews

Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

10/10 Excellent
"The airport shuttle was easy to find and prompt."
Autumn 1-night trip
Posted 5 hours ago
Spark by Hilton Portland Airport Maine Mall

Find out more about Windham

Windham Cottages information

Number of reviews
261
Accommodation
429 Cottages
Lowest Price
£248
Highest Price
£868

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between £248 and £868 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 429 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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