A white church with a steeple and red accents, surrounded by autumn trees.

Book a Windham Cottage

  • 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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (4 reviews)
"Amazing property & so many things to do around the area, we will definitely try to come back!!"
United States
Alyssa
The price is NZ$517
includes taxes & fees
21 Oct - 22 Oct
Cozy 1-bedroom cottage in soothing Standish with AC
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.

2. 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, (22 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is NZ$1,137
includes taxes & fees
25 Oct - 26 Oct
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A two-story house with a front porch, a garage, and a well-maintained lawn.

3. 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, (96 reviews)
"Very clean and my dog loved the fenced in yard"
United States
Jackie S.
The price is NZ$467
includes taxes & fees
15 Oct - 16 Oct
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

4. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (25 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 NZ$553
includes taxes & fees
1 Nov - 2 Nov
Little Miss Cottages - One Bedroom Cottage
A room with a bed, a round wooden table, a ceiling fan, a TV on the wall, and a door leading to another room.

5. 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)
"Super comfortable beds! Small cozy cottage, but with so much to do in town who needs more space?"
United States
John G.
The price is NZ$507
includes taxes & fees
4 Nov - 5 Nov
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
A pier with a building on stilts over the beach.

6. 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 NZ$495
includes taxes & fees
25 Oct - 26 Oct
beautiful 1 bedroom cabin only 50 ft from beach
A small, single-story house with a number '20' on the front, a front door, and a small porch with steps leading up to it.

7. Soothing 2-bedroom cottage with Sauna in Old Orchard Beach

Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
Old Orchard Beach
10.0 out of 10, Exceptional, (2 reviews)
"Great place. Would stay again!!"
United States
Jay T.
The price is NZ$758
includes taxes & fees
18 Oct - 19 Oct
Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
A wooden pier with multiple pillars extending into the water.

8. 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, (4 reviews)
"Great place, dog friendly and very close the beach! Perfect little getaway!"
United States
Jenna M.
The price is NZ$498
includes taxes & fees
25 Oct - 26 Oct
Attractive 1 bedroom cabin only 50 ft from beach
A two-story house with a garage and a covered porch.

9. 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 NZ$577
includes taxes & fees
1 Nov - 2 Nov
1 Mi to Maine Street! Mcm-style Home in Brunswick
A rustic building with a pond, stone pathway, and flower beds.

10. 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 NZ$498
includes taxes & fees
25 Oct - 26 Oct
Cheerful 1 bedroom cottage only 50ft from beach
A pier extending into calm waters with a building at the end.

11. 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 NZ$498
includes taxes & fees
9 Nov - 10 Nov
Cozy one bedroom cottage, 50 feet from the beach in OOB.
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, (10 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
The price is NZ$498
includes taxes & fees
25 Oct - 26 Oct
Adorable 1 bedroom cabin only 50 ft from beach#1
A white wooden house with a white picket fence, a small porch, and a window with shutters.

13. Spacious 2 bedroom cabin, 50ft from the beach

Spacious 2 bedroom cabin, 50ft from the beach
Old Orchard Beach
9.0 out of 10, Wonderful, (4 reviews)
"Clean room, friendly host, a nice part of the beach that you walk out to."
United States
Beverley R.
The price is NZ$592
includes taxes & fees
19 Oct - 20 Oct
Spacious 2 bedroom cabin, 50ft from the beach
A lakeside house with a dock, a small boathouse, and a flag.

14. Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table

Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
Brownfield
10.0 out of 10, Exceptional, (6 reviews)
"Everything was great for check in, and the amenities and snacks there were a great touch! Came in handy for the couple that forgot to pack their toothbrushes! "
United States
Brian A.
The price is NZ$589
includes taxes & fees
4 Nov - 5 Nov
Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
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
6.4 out of 10, (5 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 NZ$675
includes taxes & fees
15 Oct - 16 Oct
Little Miss Cottages - Two Bedroom Cottage Suite - 9
A beach with people, a pier, and an American flag.

16. 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
8.2 out of 10, Very good, (28 reviews)
"Even though the property was small it was spacious for two people especially my husband and I we had an awesome awesome week there the host was unbelievably kind the woman Kathy that clean the unit was exceptional and very very nice the neighborhood was peaceful and it was very convenient to the pier and all the shops definitely will be staying there from now on every year it was awesome"
United States
Catherine
The price is NZ$631
includes taxes & fees
13 Nov - 14 Nov
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.
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

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"The weight room and Spa was open both times when I went into it it was very nice"
DANA 2-night trip
Posted 1 hour ago
Fireside Inn & Suites Portland

Find out more about Windham

Windham Cottages information

Number of reviews
123
Accommodation
435 Cottages
Lowest Price
NZ$467
Highest Price
NZ$1,137

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between NZ$467 and NZ$1,137 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 435 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.
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