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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Windham and around

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Relax on the deck with a comfortable sofa set and enjoy the serene lake view.

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
Exterior

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.
Stroll through the charming garden, featuring a tree with vibrant foliage and a wooden bench on the covered porch.

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.
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Relax in a serene outdoor setting with Adirondack chairs and a table overlooking the distant shoreline.

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
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
Enjoy a peaceful retreat on this single-story home's deck, surrounded by lush trees and a clear sky.

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
WATERFRONT ON PETTENGILL POND
Escape to a serene retreat surrounded by lush greenery and a tranquil stream.

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
Stroll up to this charming home, featuring a cozy front porch surrounded by a lush garden and a beautifully maintained lawn.

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.
Escape to a serene lakeside retreat surrounded by lush forest and tranquil waters.

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.
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

10.0 out of 10, Exceptional, (4)
"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
The Great Escape - Picturesque Sebago Lake
Enjoy the serene lake view from this deck with a bench and potted plant.

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (52)
"Property was perfect for our stay."
The Great Escape - Picturesque Sebago Lake
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, (34)
"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
5 Sept - 6 Sept
Large 2BD cottage 10 min to Pier & Beach Pets ok
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!
Situated in a suburban setting, this two-story home features a curved balcony and a mix of siding materials.

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

9.6 out of 10, Exceptional, (46)
"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
Escape to a secluded cabin surrounded by a serene forest, perfect for those seeking tranquility.

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

9.8 out of 10, Exceptional, (119)
"I stayed at the end of April, so it was very quiet. The location is great right on the river. The cabin is cozy. Host was very responsive and friendly."
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
3 BR Lake house in Sebago Maine steps from beach!
Enjoy outdoor dining on the porch with a tranquil view of the surrounding trees.

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!
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Relax on the deck with a tranquil view of the water, featuring a table, Adirondack chairs, and a shaded area.

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.4 out of 10, Exceptional, (16)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Quaint Cottage Just Steps From The Beach And The Saco River
Traditional two-story house with a charming porch and American flag.

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
Dock + Fire Pit: Secluded Cottage in Denmark
Relax on the lakeside patio with a table and chairs, surrounded by dense trees and a serene lake.

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
Last Min Summer Availability: Lakefront Home!
Enjoy outdoor cooking on the deck, where a modern electric grill awaits.

Last Min Summer Availability: Lakefront Home!

9.4 out of 10, Exceptional, (22)
"We enjoyed our stay. It was comfy cozy."
Last Min Summer Availability: Lakefront Home!
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Relax on the dockside deck, surrounded by lush greenery and picturesque views of the marina.

'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!

10.0 out of 10, Exceptional, (12)
"Really enjoyed the house and location."
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
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

La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

10/10 Excellent
"I liked that it was so close to the airport I had a 6am flight "
Angela 3-night trip
Posted 9 hours ago
La Quinta Inn & Suites by Wyndham 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.