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Check prices for these dates

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 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

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, (38)
"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

10.0 out of 10, Exceptional, (2)
"I cannot think of a single thing our host Emily could have done to make our stay even better. Her communucation was excellent. The property is spotless, well appointed, tastefully decorated and exceedingly comfortable. Great bed and shower. Soothing hot tub. Front and back decks to enjoy.The easy access to the lake, with the use of a canoe and paddleboards was a joy. Emily made herself available to answer all questions and provide splendid hospitality. I cannot recommend this property highly...
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, (46)
"We had a great visit!!"
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
WATERFRONT ON PETTENGILL POND
Property grounds

WATERFRONT ON PETTENGILL POND

10.0 out of 10, Exceptional, (2)
"had a wonderful stay at this cabin, beautiful lake view with plenty of bass to catch. the owners were very accomidating to us and the check in check out was very simple. i will definitely be staying again!"
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, (82)
"Place was great "
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, (8)
"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, (16)
"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, (1)
"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, (30)
"This 2 bedroom cottage was perfect for our 3 day stay.Location was a 10 minute walk to the boardwalk.Would like to come back in the summer."
The price is €433
includes taxes & fees
14 Jul - 15 Jul
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, (49)
"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, (27)
"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

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, (21)
"Nice cabin with great views. Quiet and secluded"
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, (49)
"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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Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between €433 and €433 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 381 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.