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Check prices for these dates

Next weekend
26 Sept - 28 Sept
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

Featured Cottages in Windham and around

Private Contemporary Artist's Tree House on two acres with perennial gardens.
Exterior

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (48)
"Beautiful, fun space. Very comfortable, and accommodating. Great location and hosts!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Exterior

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (7)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (60)
"My stay at the cottage was exactly what I needed, it’s an updated beachy vibe and excellent use of every space including some rainy day puzzles and books! The small fenced in yard was perfect for the furry family members, and you cant beat the location, such a close walk to the beach, and just far enough away from the busy OOB hustle! Would definitely stay again! "
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
WATERFRONT ON PETTENGILL POND
Exterior

WATERFRONT ON PETTENGILL POND

9.6 out of 10, Exceptional, (4)
"My kids and I loved our stay at the pond. We enjoyed kayaking and floating in the peaceful setting. "
WATERFRONT ON PETTENGILL POND
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Terrace/patio

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (39)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Professionally styled waterfront cottage on Sebago. Cozy and Serene.
Exterior

Professionally styled waterfront cottage on Sebago. Cozy and Serene.

10.0 out of 10, Exceptional, (17)
"Good location, good fishing"
Professionally styled waterfront cottage on Sebago. Cozy and Serene.
Lakefront Cottage - private dock, large decks, large fire pit
Outdoor dining

Lakefront Cottage - private dock, large decks, large fire pit

9.2 out of 10, Wonderful, (25)
"Good location "
Lakefront Cottage - private dock, large decks, large fire pit
Lakefront Traditional 4-bedroom cottage in Frye Island
Exterior

Lakefront Traditional 4-bedroom cottage in Frye Island

2.0 star property
10.0 out of 10, Exceptional, (2)
"Our family of four (with older kids) had a peaceful and memorable stay at this cozy lakefront cottage. The setting is stunning—perfect for disconnecting and enjoying nature. The cottage is right on the water with a dock (no beach, but several are nearby), and we loved kayaking and watching sunsets from the deck.Some rooms are a bit tight, and Frye Island’s ferry access and dirt roads can be inconvenient—but if you’re looking for quiet, beauty, and simplicity, it’s worth it. The owner was...
Lakefront Traditional 4-bedroom cottage in Frye Island
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.0 out of 10, Wonderful, (36)
"Easy walk into the board walk shopping area ! Private parking and owner was readily available for any issues or concerns....gas station and lobster pound close enough i walked to pick us up dinner....5 lobster fresh cooked $45 and we're still steaming hot by time i walked back to the house"
The price is €401
includes taxes & fees
22 Oct - 23 Oct
Large 2BD cottage 10 min to Pier & Beach Pets ok
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Exterior

Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

9.4 out of 10, Exceptional, (9)
"We recently rented this for a quick family vacation and it exceeded our expectations. Can't wait to go back next summer!"
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Property grounds

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.4 out of 10, Exceptional, (88)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
Beach

GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗

9.8 out of 10, Exceptional, (82)
"Clean and well equipped property with a convenient location to Nassan Beach. Comfortable stay and my family had a great time. Would recommend to others."
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Terrace/patio

Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!

9.8 out of 10, Exceptional, (33)
"Clean, cute cottage for four on a steep waterfront lot with a beautiful vista. Nice kitchen for exended stay. Great fireplace."
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Coastal Charm 2 Bedroom Beach Cottage ~Just Steps to the Beach in Kinney Shores~
Exterior

Coastal Charm 2 Bedroom Beach Cottage ~Just Steps to the Beach in Kinney Shores~

10.0 out of 10, Exceptional, (5)
Coastal Charm 2 Bedroom Beach Cottage ~Just Steps to the Beach in Kinney Shores~
Glamorous cottage-glamping at Sebago Lake
Terrace/patio

Glamorous cottage-glamping at Sebago Lake

9.8 out of 10, Exceptional, (80)
"We had an amazing time at Bo and Frank’s and would love to come back in the future!"
Glamorous cottage-glamping at Sebago Lake
Cozy countryside cottage located on Crooked river in Naples Maine.
Exterior

Cozy countryside cottage located on Crooked river in Naples Maine.

10.0 out of 10, Exceptional, (17)
"Cute place with lots of thoughtful amenities that made the stay wonderful. "
Cozy countryside cottage located on Crooked river in Naples Maine.
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
Terrace/patio

Ocean Watch - Relax and let the ocean sweep you away at this charming retreat

8.6 out of 10, Excellent, (20)
"Very beautiful and easy to communicate with the property management "
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
3 BR Lake house in Sebago Maine steps from beach!
Exterior

3 BR Lake house in Sebago Maine steps from beach!

10.0 out of 10, Exceptional, (2)
"Great house to stay at. We had the perfect week! Huge thanks Nelson family."
3 BR Lake house in Sebago Maine steps from beach!
Luxurious Beachfront New England Cottage
Property grounds

Luxurious Beachfront New England Cottage

10.0 out of 10, Exceptional, (6)
"This house was gorgeous and we highly enjoyed our stay. We will be back!!"
Luxurious Beachfront New England Cottage
Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool
Exterior

Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool

10.0 out of 10, Exceptional, (4)
"It was a great stay. The house is in wonderful condition. The hosts were very helpful and our stay was relaxing and enjoyable. "
Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"We were a 3-10 minute from almost everything. "
Melinda 6-night trip
Posted 3 days ago
Portland Regency Hotel & Spa

Find out more about Windham

Find out more about Windham

Windham Cottages information

Number of reviews
558
Accommodation
458 Cottages
Lowest Price
€401
Highest Price
€401

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between €401 and €401 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.

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