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

Search Windham Cottage Rentals from CA $266

  • 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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Windham cottages

Bathroom

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

Cozy 1-bedroom cottage in soothing Standish with AC
Standish
The price is CA $242
CA $487 total
includes taxes & fees
Sep 20 - Sep 21
Cozy 1-bedroom cottage in soothing Standish with AC
Exterior

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, (18 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is CA $473
CA $819 total
includes taxes & fees
Oct 6 - Oct 7
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Outdoor dining

3. 'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (23 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 $455
CA $894 total
includes taxes & fees
Sep 30 - Oct 1
'Osprey Cottage' South Freeport Home on Casco Bay!
Cottage (2 Bedrooms) | Interior

4. '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 $547
CA $850 total
includes taxes & fees
Sep 30 - Oct 1
'osprey Cottage' South Freeport Home on Casco Bay!
Exterior

5. Cottages by the Sea #1 by Bayley Vacation Rentals

Cottages by the Sea #1 by Bayley Vacation Rentals
Surfside
9.8 out of 10, Exceptional, (9 reviews)
"Clean place, had everything we needed, and can’t beat the location. Will definitely be back."
United States
Matthew J.
Cottages by the Sea #1 by Bayley Vacation Rentals
Exterior

6. 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, (90 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 CA $311
CA $517 total
includes taxes & fees
Sep 21 - Sep 22
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

7. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.0 out of 10, Wonderful, (18 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 $211
CA $521 total
includes taxes & fees
Sep 8 - Sep 9
Little Miss Cottages - One Bedroom Cottage
Exterior

8. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
The price is CA $216
CA $266 total
includes taxes & fees
Sep 12 - Sep 13
Charming Rustic Cottage
Exterior

9. •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 CA $309
CA $817 total
includes taxes & fees
Oct 1 - Oct 2
•Tranquil 2BR Summer Home•Steps to Private Beach•
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 CA $151
CA $414 total
includes taxes & fees
Sep 28 - Sep 29
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
Exterior

11. Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful place!"
United States
Louise P.
The price is CA $231
CA $1,140 total
includes taxes & fees
Sep 23 - Sep 24
Nautical View
Beach

12. 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 CA $248
CA $439 total
includes taxes & fees
Sep 14 - Sep 15
Attractive 1 bedroom cabin only 50 ft from beach
Property grounds

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 CA $248
CA $434 total
includes taxes & fees
Sep 15 - Sep 16
Cheerful 1 bedroom cottage only 50ft from beach
House (2 Bedrooms) | Interior

14. 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 $141
CA $375 total
includes taxes & fees
Sep 23 - Sep 24
1 Mi to Maine Street! Mcm-style Home in Brunswick
Exterior

15. 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)
The price is CA $248
CA $439 total
includes taxes & fees
Sep 14 - Sep 15
Adorable 1 bedroom cabin only 50 ft from beach#1
Interior

16. Large 2BD cottage 10 min to Pier & Beach Sleeps 6<br>- FREE parking<br>- 2 queen beds and futons in the living room<br>- smart TVs<br>- washer and dryer in the unit<br>- picnic table and grill (shared)

Large 2BD cottage 10 min to Pier & Beach Sleeps 6<br>- FREE parking<br>- 2 queen beds and futons in the living room<br>- smart TVs<br>- washer and dryer in the unit<br>- picnic table and grill (shared)
Old Orchard Beach
9.0 out of 10, Wonderful, (45 reviews)
"Clean and convenient. Perfect little place to stay for a spring break in OOB"
United States
Anneliese H.
The price is CA $155
CA $476 total
includes taxes & fees
Sep 29 - Sep 30
Large 2BD cottage 10 min to Pier & Beach Sleeps 6<br>- FREE parking<br>- 2 queen beds and futons in the living room<br>- smart TVs<br>- washer and dryer in the unit<br>- picnic table and grill (shared)
Beach

17. 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 CA $248
CA $434 total
includes taxes & fees
Sep 21 - Sep 22
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Exterior

18. 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 $248
CA $434 total
includes taxes & fees
Sep 16 - Sep 17
Attractive 1 bedroom cabin only 50 ft from beach
Beach

19. 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, (26 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 $164
CA $426 total
includes taxes & fees
Oct 7 - Oct 8
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
Exterior

20. 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 CA $317
CA $567 total
includes taxes & fees
Sep 8 - Sep 9
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"Richard is where he should be"
Jason 1-night trip
Posted less than an hour ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Windham

Windham Cottages information

Number of reviews
156
Accommodation
420 Cottages
Lowest Price
CA $266
Highest Price
CA $1,140

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between CA $266 and CA $1,140 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 420 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