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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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, (17 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 NZ$1,232
includes taxes & fees
2 Sept - 3 Sept
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Exterior

2. 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

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, (87 reviews)
"Perfect getaway cottage for my husband & me & our 2 small dogs. And a fenced-in yard!"
United States
Margaret K.
The price is NZ$543
includes taxes & fees
2 Sept - 3 Sept
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

4. Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.2 out of 10, Wonderful, (17 reviews)
"Clean, very good communication with the host."
United States
Brandon F.
The price is NZ$590
includes taxes & fees
1 Sept - 2 Sept
Little Miss Cottages - One Bedroom Cottage
Exterior

5. Nautical View

Nautical View
Old Orchard Beach
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful place!"
United States
Louise P.
The price is NZ$1,457
includes taxes & fees
4 Sept - 5 Sept
Nautical View
Interior

6. 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, (43 reviews)
"Clean and convenient. Perfect little place to stay for a spring break in OOB"
United States
Anneliese H.
The price is NZ$562
includes taxes & fees
29 Sept - 30 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)
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 NZ$560
includes taxes & fees
1 Sept - 2 Sept
Cheerful 1 bedroom cottage only 50ft from beach
Exterior

8. Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
The price is NZ$441
includes taxes & fees
12 Sept - 13 Sept
Charming Rustic Cottage
House (2 Bedrooms) | Interior

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$458
includes taxes & fees
23 Sept - 24 Sept
1 Mi to Maine Street! Mcm-style Home in Brunswick
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 NZ$463
includes taxes & fees
29 Sept - 30 Sept
Renovated 2Bd Cottage 10min walk to Beach.<br>- Pet friendly<br>- FREE parking<br>- 2 queen beds and futon<br>- smart TVs
Beach nearby

11. 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 NZ$560
includes taxes & fees
31 Aug - 1 Sept
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

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, (8 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
The price is NZ$560
includes taxes & fees
31 Aug - 1 Sept
Adorable 1 bedroom cabin only 50 ft from beach#1
Beach

13. 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 NZ$529
includes taxes & fees
29 Sept - 30 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

14. 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 NZ$560
includes taxes & fees
31 Aug - 1 Sept
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Exterior

15. Little Miss Cottages - Two Bedroom Cottage Suite - 9

Little Miss Cottages - Two Bedroom Cottage Suite - 9
Old Orchard Beach
5.4 out of 10, (3 reviews)
"WiFi and tv was spotty on a good day and non existent towards the end of our stay. If we were to go again I wouldn’t want to stay in suite 9. Some of the other cottages were a little more secluded and had a deck."
United States
Ralph B.
The price is NZ$720
includes taxes & fees
2 Sept - 3 Sept
Little Miss Cottages - Two Bedroom Cottage Suite - 9
Beach nearby

16. 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$560
includes taxes & fees
31 Aug - 1 Sept
beautiful 1 bedroom cabin only 50 ft from beach
Exterior

17. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
The price is NZ$560
includes taxes & fees
2 Sept - 3 Sept
Attractive 1 bedroom cabin only 50 ft from beach
Exterior

18. 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 NZ$816
includes taxes & fees
29 Sept - 30 Sept
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.
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Top Windham Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"Helpful staff and the shuttle to/from airport and back and forth from downtown was really great."
DeeDee 4-night trip
Posted 11 hours ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Windham

Windham Cottages information

Number of reviews
259
Accommodation
416 Cottages
Lowest Price
NZ$441
Highest Price
NZ$1,457

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between NZ$441 and NZ$1,457 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 416 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.

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