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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 CA $190
CA $429 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $475
CA $833 total
includes taxes & fees
Nov 19 - Nov 20
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, (98 reviews)
"Pet friendly, clean cottage in quiet neighborhood."
United States
Alejandra
The price is CA $186
CA $359 total
includes taxes & fees
Nov 1 - Nov 2
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
A wooden pier with multiple pillars extending into the water.

4. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
9.6 out of 10, Exceptional, (5 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 CA $195
CA $375 total
includes taxes & fees
Oct 25 - Oct 26
Attractive 1 bedroom cabin only 50 ft from beach
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

5. 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 CA $153
CA $454 total
includes taxes & fees
Oct 25 - Oct 26
Little Miss Cottages - One Bedroom Cottage
A two-story house with a garage and a covered porch.

6. 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 $211
CA $454 total
includes taxes & fees
Nov 1 - Nov 2
1 Mi to Maine Street! Mcm-style Home in Brunswick
A beach with people, a pier, and an American flag.

7. 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 CA $187
CA $461 total
includes taxes & fees
Nov 19 - Nov 20
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
A lakeside cabin with a deck, surrounded by dense trees.

8. Lake Front Taylor Pond Cottage

Lake Front Taylor Pond Cottage
Auburn
10.0 out of 10, Exceptional, (3 reviews)
"Great place! Immaculate and had everything we needed."
United States
Tracy V.
The price is CA $411
CA $636 total
includes taxes & fees
Nov 3 - Nov 4
Lake Front Taylor Pond Cottage
A pier extending into calm waters with a building at the end.

9. 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)
The price is CA $195
CA $375 total
includes taxes & fees
Oct 25 - Oct 26
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.

10. 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 CA $195
CA $375 total
includes taxes & fees
Oct 25 - Oct 26
Adorable 1 bedroom cabin only 50 ft from beach#1
A pier with a building on stilts over the beach.

11. 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 CA $195
CA $375 total
includes taxes & fees
Oct 25 - Oct 26
beautiful 1 bedroom cabin only 50 ft from beach
A rustic building with a pond, stone pathway, and flower beds.

12. 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 CA $195
CA $371 total
includes taxes & fees
Oct 27 - Oct 28
Cheerful 1 bedroom cottage only 50ft from beach
A lakeside house with a dock, a small boathouse, and a flag.

13. 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)
"Great little camp with lake access! Thanks for hosting us :-)"
United States
Anonymous traveller
The price is CA $255
CA $496 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
A room with a bed, a round wooden table, a ceiling fan, a TV on the wall, and a door leading to another room.

14. 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 CA $142
CA $407 total
includes taxes & fees
Oct 23 - Oct 24
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- 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.
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Top Windham Hotel Reviews

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

8/10 Good
"It was just what we needed. It was close enough to the airport and Portland and parking and breakfast were free! My only complaint is the room had a very strong bleach smell. I appreciated that everything was clean, but the smell gave me a headache and was stuck in my throat."
Anna 1-night trip
Posted less than an hour ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Windham

Windham Cottages information

Number of reviews
219
Accommodation
435 Cottages
Lowest Price
CA $359
Highest Price
CA $833

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between CA $359 and CA $833 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.
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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