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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Windham cottages

A two-story building with a metal exterior, a door with a cactus and a cow design, and three windows with decorative panels.

1. Cozy 1-bedroom cottage in soothing Standish with AC

Cozy 1-bedroom cottage in soothing Standish with AC
Standish
10.0 out of 10, Exceptional, (2 reviews)
"Amazing property & so many things to do around the area, we will definitely try to come back!!"
United States
Alyssa
The price is AU$466
includes taxes & fees
28 Sept - 29 Sept
Cozy 1-bedroom cottage in soothing Standish with AC
A two-story house with a gabled roof and a front porch.

2. 3BR Cottage Parking A Peaceful Oasis on Munjoy Hill

3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (2 reviews)
"Super clean and spacious in a walkable area. "
United States
Nell F.
3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
A two-story house with a white exterior and a black base. There is a white staircase leading to the front door, surrounded by lush greenery and flowering plants.

3. 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, (20 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is AU$837
includes taxes & fees
28 Sept - 29 Sept
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A two-story house with a front porch, a garage, and a well-maintained lawn.

4. 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, (92 reviews)
"Great, pet-friendly spot! Walkable to the beach, places to eat, etc. Loved the space (indoor and outdoor) to spread out a bit."
United States
Blake S.
The price is AU$379
includes taxes & fees
6 Oct - 7 Oct
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
A covered outdoor area with a table and chairs, a view of the water, and a wooden deck.

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

Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed
SEBAGO
10.0 out of 10, Exceptional, (1 review)
"Absolutely beautiful location. Quiet area on the lake and great sunrises. Will definitely go back."
United States
Christian R.
The price is AU$1,200
includes taxes & fees
13 Oct - 14 Oct
Sebago Waterfront-Large Private Lot, Dock, Screened Porch, Grill. Pets Allowed
A small house with a wooden deck and a porch.

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

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
10.0 out of 10, Exceptional, (1 review)
The price is AU$642
includes taxes & fees
1 Oct - 2 Oct
•Tranquil 2BR Summer Home•Steps to Private Beach•
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

7. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (23 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 AU$435
includes taxes & fees
28 Sept - 29 Sept
Little Miss Cottages - One Bedroom Cottage

8. Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings

Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Biddeford Pool
9.4 out of 10, Exceptional, (60 reviews)
"We love this place. Our dogs enjoy coming."
United States
amy b.
The price is AU$1,096
includes taxes & fees
28 Sept - 29 Sept
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
A wooden pier with multiple pillars extending into the water.

9. 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 AU$412
includes taxes & fees
5 Oct - 6 Oct
Attractive 1 bedroom cabin only 50 ft from beach
A room with a bed, a round wooden table, a ceiling fan, a TV on the wall, and a door leading to another room.

10. 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 AU$438
includes taxes & fees
28 Oct - 29 Oct
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
A two-story house with a garage and a covered porch.

11. 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
A two-story house with a front porch, a bench, and a well-maintained lawn.

12. 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, (9 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
The price is AU$414
includes taxes & fees
30 Sept - 1 Oct
Adorable 1 bedroom cabin only 50 ft from beach#1
A rustic building with a pond, stone pathway, and flower beds.

13. 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 AU$414
includes taxes & fees
30 Sept - 1 Oct
Cheerful 1 bedroom cottage only 50ft from beach
A pier extending into calm waters with a building at the end.

14. 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
9.8 out of 10, Exceptional, (6 reviews)
"Great location to the beach and the pier! "
United States
Pamela C.
The price is AU$414
includes taxes & fees
30 Sept - 1 Oct
Cozy one bedroom cottage, 50 feet from the beach in OOB.
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

15. Little Miss Cottages - Two Bedroom Cottage Suite - 9

Little Miss Cottages - Two Bedroom Cottage Suite - 9
Old Orchard Beach
6.6 out of 10, (4 reviews)
"WiFi and tv was spotty on a good day and non existent towards the end of our stay. If we were to go again I wouldn’t want to stay in suite 9. Some of the other cottages were a little more secluded and had a deck."
United States
Ralph B.
The price is AU$542
includes taxes & fees
28 Sept - 29 Sept
Little Miss Cottages - Two Bedroom Cottage Suite - 9
A pier with a building on stilts over the beach.

16. beautiful 1 bedroom cabin only 50 ft from beach

beautiful 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Being so close to the water was great. Place was a little smaller than we typically get but sufficient and was very clean. The owner was great to communicate with and quick to respond to questions. We particularly liked the shaded patio area in front."
United States
Allan S.
The price is AU$414
includes taxes & fees
30 Sept - 1 Oct
beautiful 1 bedroom cabin only 50 ft from beach
An aerial view of a residential area with numbered houses, a central patio with outdoor furniture, and surrounding greenery.

17. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
The price is AU$1,168
includes taxes & fees
13 Oct - 14 Oct
Attractive 1 bedroom cabin only 50 ft from beach
A white wooden house with a white picket fence, a small porch, and a window with shutters.

18. 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 AU$553
includes taxes & fees
18 Oct - 19 Oct
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.
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Top Windham Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Excellent hotel! Loved it!"
Teresa 2-night trip
Posted 1 hour ago
Portland Harbor Hotel

Find out more about Windham

Windham Cottages information

Number of reviews
239
Accommodation
432 Cottages
Lowest Price
AU$379
Highest Price
AU$1,200

Frequently asked questions

How much do cottages in Windham cost?
Prices for cottages in Windham range between AU$379 and AU$1,200 per night. Whatever your budget, you're sure to find a perfect place to get reacquainted with nature. This price was 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?
Surround yourself with nature in one of the 432 cottages waiting for you in Windham. To help you find your ideal place, use our handy filter tool to search for perks or amenities you need.
What is there to do in Windham near my cottage?
Windham has enough sights and activities to keep you going for weeks, beginning with Seacoast Adventure. Maine Wildlife Park, Childrens Museum and Theatre of Maine and Southworth Planetarium are other wonderful attractions. If you're sticking around a while, Thompsons Point and University of Southern Maine are nice final touches to your itinerary.

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