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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Cottages in Windham

Exterior
The Outlet House, Comfortable Cottage

Cottage in Freeport

9.8 out of 10, Exceptional, (49)
"Fantastic house in a great location! Will definitely be back"
United States
Brandon G.
The price is SAR 422
SAR 796 total
includes taxes & fees
7 Dec - 8 Dec
The Outlet House, Comfortable Cottage
Private kitchen
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok

Cottage in Old Orchard Beach

7.2 out of 10, Good, (12)
"Was as advertised."
United States
Andrew H.
The price is SAR 300
SAR 716 total
includes taxes & fees
3 Dec - 4 Dec
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
Exterior
Adorable 1 bedroom cabin only 50 ft from beach#1

Cottage in Old Orchard Beach

10.0 out of 10, Exceptional, (3)
"The location was wonderful! The host was so communicative and kind!"
United States
Courtney W.
The price is SAR 559
SAR 928 total
includes taxes & fees
14 Dec - 15 Dec
Adorable 1 bedroom cabin only 50 ft from beach#1
Exterior
Little Miss Cottages - One Bedroom Cottage

Cottage in Old Orchard Beach

10.0 out of 10, Exceptional, (1)
"Clean, very good communication with the host."
United States
Brandon F.
The price is SAR 677
SAR 1,306 total
includes taxes & fees
1 Jan - 2 January 2026
Little Miss Cottages - One Bedroom Cottage
Exterior
The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach

Cottage in Surfside

10.0 out of 10, Exceptional, (3)
"Great place for a family retreat "
United States
joey r.
The price is SAR 1,407
SAR 2,688 total
includes taxes & fees
14 Dec - 15 Dec
The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach
Exterior
Cheerful 1 bedroom cottage only 50ft from beach

Cottage in Old Orchard Beach

10.0 out of 10, Exceptional, (2)
"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 SAR 559
SAR 929 total
includes taxes & fees
12 Dec - 13 Dec
Cheerful 1 bedroom cottage only 50ft from beach
Beach nearby
Cozy one bedroom cottage, 50 feet from the beach in OOB.

Cottage in Old Orchard Beach

9.6 out of 10, Exceptional, (4)
"Great location to the beach and the pier! "
United States
Pamela C.
The price is SAR 559
SAR 929 total
includes taxes & fees
14 Dec - 15 Dec
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Exterior detail
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Cottage in Old Orchard Beach

8.0 out of 10, Very Good, (24)
"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 SAR 375
SAR 810 total
includes taxes & fees
3 Dec - 4 Dec
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Exterior
Spacious 2 bedroom cabin, 50ft from the beach

Cottage in Old Orchard Beach

The price is SAR 634
SAR 1,129 total
includes taxes & fees
2 Jan - 3 January 2026
Spacious 2 bedroom cabin, 50ft from the beach
Exterior
Large 2BD cottage 10 min to Pier & Beach Pets ok

Cottage in Old Orchard Beach

9.0 out of 10, Wonderful, (36)
"Wondeful place to stay while in the area. EASY walk to the beach and all that the boardwalk area has to offer. "
United States
Steven D.
The price is SAR 375
SAR 810 total
includes taxes & fees
15 Dec - 16 Dec
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior
Attractive 1 bedroom cabin only 50 ft from beach

Cottage in Old Orchard Beach

The price is SAR 559
SAR 974 total
includes taxes & fees
14 Dec - 15 Dec
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby
beautiful 1 bedroom cabin only 50 ft from beach

Cottage in Old Orchard Beach

The price is SAR 559
SAR 929 total
includes taxes & fees
12 Dec - 13 Dec
beautiful 1 bedroom cabin only 50 ft from beach
Beach nearby
Attractive 1 bedroom cabin only 50 ft from beach

Cottage in Old Orchard Beach

The price is SAR 559
SAR 929 total
includes taxes & fees
14 Dec - 15 Dec
Attractive 1 bedroom cabin only 50 ft from beach
Exterior
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile

Cottage in Brownfield

10.0 out of 10, Exceptional, (3)
"Everything was great for check in, and the amenities and snacks there were a great touch! Came in handy for the couple that forgot to pack their toothbrushes! "
United States
Brian A.
The price is SAR 480
SAR 1,068 total
includes taxes & fees
9 Dec - 10 Dec
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
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

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"Easy check in, cozy and clean 👍"
Kathryn 2-night trip
Posted 1 day ago
Fireside Inn & Suites Portland

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between SAR 716 and SAR 2,659 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 458 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.