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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Windham cottages

Exterior

1. 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 €661
includes taxes & fees
2 Sept - 3 Sept
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

2. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
The price is €202
includes taxes & fees
13 Aug - 14 Aug
Charming Rustic Cottage
2 bedrooms, iron/ironing board, free WiFi, bed sheets

3. 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 €302
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

4. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (11 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
The price is €390
includes taxes & fees
1 Sept - 2 Sept
Little Miss Cottages - One Bedroom Cottage
Exterior

5. 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.
Soothing 2-bedroom cottage with Sauna in Old Orchard Beach
Exterior

6. Cottage by the Sea #3 by Bayley Vacation Rentals

Cottage by the Sea #3 by Bayley Vacation Rentals
Surfside
8.6 out of 10, Excellent, (4 reviews)
"Great location and cottage! Views of the beach are unbeatable."
United States
Nathan M.
The price is €1,187
includes taxes & fees
15 Aug - 16 Aug
Cottage by the Sea #3 by Bayley Vacation Rentals
Property grounds

7. 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 €401
includes taxes & fees
7 Sept - 8 Sept
Cheerful 1 bedroom cottage only 50ft from beach
House (2 Bedrooms) | Interior

8. 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 €252
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Maine Street! Mcm-style Home in Brunswick
Interior

9. 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, (41 reviews)
"Clean and convenient. Perfect little place to stay for a spring break in OOB"
United States
Anneliese H.
The price is €344
includes taxes & fees
7 Sept - 8 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)
Exterior

10. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
The price is €436
includes taxes & fees
7 Sept - 8 Sept
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

11. 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 €389
includes taxes & fees
7 Sept - 8 Sept
Adorable 1 bedroom cabin only 50 ft from beach#1
Beach nearby

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 €470
includes taxes & fees
7 Sept - 8 Sept
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

13. 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 €507
includes taxes & fees
14 Aug - 15 Aug
Cozy one bedroom cottage, 50 feet from the beach in OOB.
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

Clarion Pointe South Portland

Clarion Pointe South Portland

10/10 Excellent
"Good place to stay good breakfast helpful staff"
Neerav 5-night trip
Posted 1 hour ago
Clarion Pointe South Portland

Find out more about Windham

Windham Cottages information

Number of reviews
107
Accommodation
429 Cottages
Lowest Price
€202
Highest Price
€1,187

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between €202 and €1,187 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 429 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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