Search Windham Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Windham cottages

Exterior

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

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
$527 nightly
The price is $575
Jul 14 - Jul 15
Total with taxes and fees
•Tranquil 2BR Summer Home•Steps to Private Beach•
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
$310 nightly
The price is $338
Jul 16 - Jul 17
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
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, (13 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
$755 nightly
The price is $823
Jun 28 - Jun 29
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
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, (72 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful place!"
United States
Louise P.
$977 nightly
The price is $1,057
Jun 23 - Jun 24
Total with taxes and fees
Nautical View
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.
$1,351 nightly
The price is $1,463
Jul 13 - Jul 14
Total with taxes and fees
Cottages by the Sea #1 by Bayley Vacation Rentals
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, (1 review)
"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.
$449 nightly
The price is $489
Jun 21 - Jun 22
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
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 traveler
$392 nightly
The price is $396
Jun 21 - Jun 22
Total with taxes and fees
Large 2BD cottage 10 min to Pier & Beach Sleeps 6
Exterior

Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
8.8 out of 10, Excellent, (5 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
$449 nightly
The price is $489
Jun 23 - Jun 24
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Exterior

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, (5 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
$348 nightly
The price is $379
Jun 22 - Jun 23
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
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.
$361 nightly
The price is $365
Jun 21 - Jun 22
Total with taxes and fees
Updated 2 BD cottage. 10 min walk to Pier & Beach
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.
$361 nightly
The price is $365
Jun 21 - Jun 22
Total with taxes and fees
Renovated 2Bd Cottage 10min walk to 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, (4 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.
$428 nightly
The price is $467
Jun 22 - Jun 23
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
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.
$375 nightly
The price is $409
Jun 22 - Jun 23
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Exterior

Spacious 2 bedroom cabin, 50ft from the beach

Spacious 2 bedroom cabin, 50ft from the beach
Old Orchard Beach
8.0 out of 10, Very Good, (2 reviews)
"The amenities were perfect and the communication was excellent!"
United States
Dawn C.
$799 nightly
The price is $871
Jun 28 - Jun 29
Total with taxes and fees
Spacious 2 bedroom cabin, 50ft from the beach
Beach nearby

beautiful 1 bedroom cabin only 50 ft from beach

beautiful 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$375 nightly
The price is $409
Jun 22 - Jun 23
Total with taxes and fees
beautiful 1 bedroom cabin only 50 ft from beach
Exterior

Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
$424 nightly
The price is $462
Jun 21 - Jun 22
Total with taxes and fees
Attractive 1 bedroom cabin only 50 ft from beach
Outdoor dining

Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed

Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed
SEBAGO
Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed
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

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

10/10 Excellent
"We had a great stay, comfortable, clean and quiet"
Amy 1-night trip
Posted less than an hour ago
Comfort Inn South Portland Airport

Find out more about Windham

Windham Cottages information

Number of reviews
Accommodation
427 Cottages
Lowest Price
$338
Highest Price
$630

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $338 and $630 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 427 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