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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Windham and around

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Relax on the deck with a view of the calm lake, featuring comfortable seating and a barbecue grill.

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

9.6 out of 10, Exceptional, (85)
"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
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Smart TV

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

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Relax in a hot tub surrounded by a serene backyard setting.

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

10.0 out of 10, Exceptional, (39)
"Great stay. Unique place with lots of character. Clean and pleasant. Loved the geese that greeted us each time we walked in/out (fenced not loose) !"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
Relax in a comfortable seating area with a sofa and bench, surrounded by a mix of modern and rustic elements.

Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access

9.6 out of 10, Exceptional, (4)
"This was a gem, and the location was perfect for what we need. Very charming and such a comfortable bed"
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Harbor scene with boats moored at the dock.

Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings

9.6 out of 10, Exceptional, (49)
"We had a wonderful time at this house! It’s perfectly situated by the beach, just a stone’s throw away from the charming village of Biddeford Pool. You can even grab some fresh, steamed lobster at the grocery store there. The house offers breathtaking views of the sunset and the bay, and there’s plenty of great outdoor space for relaxation. Parking is also a breeze. The host is incredibly friendly and responsive, making our stay even more enjoyable. We even had a travel massage for our...
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
WATERFRONT ON PETTENGILL POND
Property grounds

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
Little Miss Cottages
Relax in a serene outdoor space with Adirondack chairs, a picnic table, and a fire pit.

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (86)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages
Professionally styled waterfront cottage on Sebago. Cozy and Serene.
Enjoy cooking and entertaining in this well-equipped kitchen with modern appliances, a dishwasher, and ample kitchenware.

Professionally styled waterfront cottage on Sebago. Cozy and Serene.

10.0 out of 10, Exceptional, (9)
"Good location, good fishing"
Professionally styled waterfront cottage on Sebago. Cozy and Serene.
100 feet from the ocean 3 bedroom cottage 420 friendly
Walk along the boardwalk to the beach, flanked by rope barriers and a welcoming sign.

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (18)
"Our family of 5 stayed here with our dog. This place has it all and we wanted for nothing. Stocked with towels, everything you would need in the kitchen. There’s even a washer and dryer on site. Right next the beach and a short walk to the pier. It was very clean and well taken care of. We will definitely be back!"
100 feet from the ocean 3 bedroom cottage 420 friendly
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (2)
"Cute cabin in small quiet campground close to pool and short walk to downtown. The cabin itself was clean, cozy, and had everything we needed for a comfortable stay. Perfect for a small family getaway or a relaxing weekend."
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Large 2BD cottage 10 min to Pier & Beach Pets ok
Stroll up to the charming entrance, where a front porch invites you to relax.

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

9.0 out of 10, Wonderful, (33)
"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 €382
includes taxes & fees
31 Jul - 1 Aug
Large 2BD cottage 10 min to Pier & Beach Pets ok
The Great Escape - Picturesque Sebago Lake
Relax in this spacious loft-style living area with a stone fireplace, dining table, and comfortable seating area.

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (50)
"Property was perfect for our stay."
The Great Escape - Picturesque Sebago Lake
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Enjoy the ocean views from this deck overlooking the coastline.

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

9.8 out of 10, Exceptional, (29)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Walk along the beach pathway to the ocean's edge.

Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!

9.6 out of 10, Exceptional, (45)
"We enjoyed our visit"
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
Enjoy serene waterfront views and easy access to boats at this picturesque marina.

Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

9.8 out of 10, Exceptional, (118)
"My family and I had a wonderful stay. The cabin is great, the location is beautiful and so peaceful and Kyle is a wonderful host. I would definitely want to stay there again on my next trip to Maine."
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
3 BR Lake house in Sebago Maine steps from beach!
Enjoy a serene beach experience with calm waters and opportunities for boating.

3 BR Lake house in Sebago Maine steps from beach!

10.0 out of 10, Exceptional, (1)
"Close to the beach boat rentals and restaurants. Far enough away from the noise. Clean house with all the amenities needed. Philip was great and always available."
3 BR Lake house in Sebago Maine steps from beach!
Dock + Fire Pit: Secluded Cottage in Denmark
Enjoy cooking in this well-equipped kitchen with a stainless steel stove, microwave, and oven.

Dock + Fire Pit: Secluded Cottage in Denmark

8.0 out of 10, Very good, (1)
"The lake is beautiful and all of the kayaks and other water gear to enjoy it was much appreciated! The only thing that wasn't clearly explained in the description is that the master bedroom is its own separate structure (so you have to go outside the main cabin to get to it). This was not a problem for us because our kids are older, but if you have very small kiddos, this is important to know. But the cabin has just about everything you could possibly need, all stored very artfully in the...
Dock + Fire Pit: Secluded Cottage in Denmark
Quaint Cottage Just Steps From The Beach And The Saco River
Kitchen equipped with microwave, oven, and sink, featuring a chair and window.

Quaint Cottage Just Steps From The Beach And The Saco River

9.8 out of 10, Exceptional, (16)
"We had a very nice, clean and comfortable stay!"
Quaint Cottage Just Steps From The Beach And The Saco River
Waterfront Lake Arrowhead Home w/ Kayaks & Grill!
Relax in a spacious living area with a high ceiling, comfortable sofa, and dining space.

Waterfront Lake Arrowhead Home w/ Kayaks & Grill!

9.4 out of 10, Exceptional, (22)
"We enjoyed our stay. It was comfy cozy."
Waterfront Lake Arrowhead Home w/ Kayaks & Grill!
15A Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Enjoy a serene garden oasis with lush plants, a hedge, and a small tree, surrounded by a stone wall and outdoor dining area.

15A Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit

9.8 out of 10, Exceptional, (51)
"Convenient to all that Old Orchard Beach has to offer. Great communication and offerings of beach chairs and beach towels. Wonderful time. Definitely recommend."
15A Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
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 Hotel Portland

Clarion Hotel Portland

10/10 Excellent
"The lobby is welcoming. I mean spacious, clean and bright!"
FRANCIS 1-night trip
Posted 19 hours ago
Clarion Hotel Portland

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between €382 and €382 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.