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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Windham cottages

Exterior

1. Cottage by the Sea #4 by Bayley Vacation Rentals

Cottage by the Sea #4 by Bayley Vacation Rentals
Surfside
Cottage by the Sea #4 by Bayley Vacation Rentals
Exterior

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

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
The price is AU$738
includes taxes & fees
1 Sept - 2 Sept
•Tranquil 2BR Summer Home•Steps to Private Beach•
House (2 Bedrooms) | Interior

3. 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 AU$402
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Maine Street! Mcm-style Home in Brunswick
Exterior

4. 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, (16 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 AU$1,044
includes taxes & fees
2 Sept - 3 Sept
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

5. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
The price is AU$300
includes taxes & fees
12 Sept - 13 Sept
Charming Rustic Cottage
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
9.6 out of 10, Exceptional, (84 reviews)
"Perfect getaway cottage for my husband & me & our 2 small dogs. And a fenced-in yard!"
United States
Margaret K.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

7. Cottages By The Sea #2 by Bayley Vacation Rentals

Cottages By The Sea #2 by Bayley Vacation Rentals
Surfside
10.0 out of 10, Exceptional, (2 reviews)
"Perfect little getaway."
United States
Tish L.
Cottages By The Sea #2 by Bayley Vacation Rentals
Exterior

8. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (14 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
The price is AU$609
includes taxes & fees
7 Sept - 8 Sept
Little Miss Cottages - One Bedroom Cottage
Exterior

9. 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, (8 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
The price is AU$592
includes taxes & fees
7 Sept - 8 Sept
Adorable 1 bedroom cabin only 50 ft from beach#1
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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$548
includes taxes & fees
1 Sept - 2 Sept
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
Exterior

11. 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
Property grounds

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 AU$649
includes taxes & fees
7 Sept - 8 Sept
Cheerful 1 bedroom cottage only 50ft from beach
Interior

13. 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, (42 reviews)
"Clean and convenient. Perfect little place to stay for a spring break in OOB"
United States
Anneliese H.
The price is AU$531
includes taxes & fees
8 Sept - 9 Sept
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

14. 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
8.0 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 AU$500
includes taxes & fees
8 Sept - 9 Sept
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
Beach nearby

15. 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$592
includes taxes & fees
7 Sept - 8 Sept
beautiful 1 bedroom cabin only 50 ft from beach
Exterior

16. 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$624
includes taxes & fees
7 Sept - 8 Sept
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

17. 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$764
includes taxes & fees
7 Sept - 8 Sept
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

18. 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, (5 reviews)
"Great location to the beach and the pier! "
United States
Pamela C.
The price is AU$859
includes taxes & fees
27 Aug - 28 Aug
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Exterior

19. 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$814
includes taxes & fees
7 Sept - 8 Sept
Spacious 2 bedroom cabin, 50ft from the beach
Outdoor dining

20. 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
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

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

8/10 Good
"The room was very clean and breakfast had many options. Easy drive into Portland."
Amanda 2-night trip
Posted 3 hours ago
Quality Inn & Suites South Portland

Find out more about Windham

Windham Cottages information

Number of reviews
226
Accommodation
433 Cottages
Lowest Price
AU$300
Highest Price
AU$1,044

Frequently asked questions

How much do cottages in Windham cost?
Prices for cottages in Windham range between AU$300 and AU$1,044 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 433 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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