Search Windham Cottage Rentals from CA $373

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Windham cottages

Exterior

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

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
•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
The price is CA $236
CA $522 total
includes taxes & fees
Jul 2 - Jul 3
1 Mi to Maine Street! Mcm-style Home in Brunswick
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 CA $457
CA $895 total
includes taxes & fees
Jun 12 - Jun 13
'Osprey Cottage' South Freeport Home on Casco Bay!
Exterior

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Old Orchard Beach
9.6 out of 10, Exceptional, (72 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
The price is CA $194
CA $373 total
includes taxes & fees
Jun 9 - Jun 10
Dog Friendly, Relaxing Cottage Stay • Steps Away from The 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
10.0 out of 10, Exceptional, (5 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
The price is CA $236
CA $424 total
includes taxes & fees
Jun 8 - Jun 9
Adorable 1 bedroom cabin only 50 ft from beach#1
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, (12 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 CA $772
CA $1,205 total
includes taxes & fees
Jun 28 - Jun 29
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful place!"
United States
Louise P.
The price is CA $483
CA $1,473 total
includes taxes & fees
Jun 23 - Jun 24
Nautical View
Exterior

Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.6 out of 10, Exceptional, (4 reviews)
"It was very clean and it’s pet friendly. The host went above and beyond and was truly friendly while doing so. A great location and quiet at this time of year. The bed was very comfortable. The shower nice and hot. I would rent that seaside shanty again. "
United States
Lynne B.
The price is CA $176
CA $481 total
includes taxes & fees
Jun 8 - Jun 9
Little Miss Cottages - One Bedroom 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 CA $234
CA $513 total
includes taxes & fees
Jun 8 - Jun 9
Renovated 2Bd Cottage 10min walk to 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, (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.
The price is CA $247
CA $438 total
includes taxes & fees
Jun 8 - Jun 9
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
Cottage (2 Bedrooms) | Interior

'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
The price is CA $511
CA $878 total
includes taxes & fees
Jun 12 - Jun 13
'osprey Cottage' South Freeport Home on Casco Bay!
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.
The price is CA $249
CA $442 total
includes taxes & fees
Jun 9 - Jun 10
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.
The price is CA $459
CA $702 total
includes taxes & fees
Jun 16 - Jun 17
Cozy one bedroom cottage, 50 feet from the beach in OOB.
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 CA $236
CA $424 total
includes taxes & fees
Jun 8 - Jun 9
beautiful 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 traveller
The price is CA $222
CA $555 total
includes taxes & fees
Jun 8 - Jun 9
Large 2BD cottage 10 min to Pier & Beach Sleeps 6
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 CA $220
CA $495 total
includes taxes & fees
Jun 15 - Jun 16
Updated 2 BD cottage. 10 min walk to Pier & Beach
Exterior

Little Miss Cottages - Two Bedroom Cottage Suite - 9

Little Miss Cottages - Two Bedroom Cottage Suite - 9
Old Orchard Beach
The price is CA $313
CA $651 total
includes taxes & fees
Jun 14 - Jun 15
Little Miss Cottages - Two Bedroom Cottage Suite - 9
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 CA $474
CA $720 total
includes taxes & fees
Jun 14 - Jun 15
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
8.0 out of 10, Very good, (2 reviews)
"The amenities were perfect and the communication was excellent!"
United States
Dawn C.
The price is CA $708
CA $1,056 total
includes taxes & fees
Jun 28 - Jun 29
Spacious 2 bedroom cabin, 50ft from the 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.
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

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

8/10 Good
"Impossible to use the pool due to a large group with lots of young kids staying at the same time."
Jamie 1-night trip
Posted less than an hour ago
Embassy Suites by Hilton Portland Maine

Find out more about Windham

Windham Cottages information

Number of reviews
219
Accommodation
401 Cottages
Lowest Price
CA $373
Highest Price
CA $1,473

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between CA $373 and CA $1,473 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 401 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