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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
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, (5)
"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
Little Miss Cottages
Exterior

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
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, (3)
"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
COZY,Newly renovated,West Shores ,short walk to Nasons Beach 🏖🏠
Property grounds

COZY,Newly renovated,West Shores ,short walk to Nasons Beach 🏖🏠

9.6 out of 10, Exceptional, (81)
"Overall we had a great stay! The water is super close, the cottage is clean, comfy and cozy and has everything you need. We enjoyed fires at night and morning coffee on the hammock. Great communication as well. "
COZY,Newly renovated,West Shores ,short walk to Nasons 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
The Outlet House, Comfortable Cottage
Exterior

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (43)
"We loved our stay here! The cottage was super clean and in a quiet area within walking distance to town and all the shops and restaurants. Check-in was simple and the hosts were very friendly and responded quickly. Would definitely stay again!"
The Outlet House, Comfortable Cottage
2 bedroom cottage
Smart TV

2 bedroom cottage

9.2 out of 10, Wonderful, (5)
"quiet, clean, short walk to beach"
2 bedroom cottage
The Great Escape - Picturesque Sebago Lake
Terrace/patio

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
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

9.6 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
Cute cottage only a 10 min walk to the beach.
Exterior

Cute cottage only a 10 min walk to the beach.

10.0 out of 10, Exceptional, (9)
"Our stay was perfect. The house is really cute and well located for going to the beach."
Cute cottage only a 10 min walk to the beach.
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Property grounds

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.
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
Exterior

Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path

9.2 out of 10, Wonderful, (74)
"Loved how close it was to the beach.. very sweet little cottage."
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Exterior

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!
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Property grounds

Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!

10.0 out of 10, Exceptional, (142)
"This place is amazing. Lots of relaxation and fun was spent here. "
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
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, (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 HK$1,374
HK$2,421 total
includes taxes & fees
1 Sept - 2 Sept
Large 2BD cottage 10 min to Pier & Beach Pets ok
The Hidden Cove by Bayley Vacation Rentals
Exterior

The Hidden Cove by Bayley Vacation Rentals

9.8 out of 10, Exceptional, (23)
"Great stay"
The Hidden Cove by Bayley Vacation Rentals
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)
"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!
Charming cottage short walk to beach!
Exterior

Charming cottage short walk to beach!

9.4 out of 10, Exceptional, (30)
"This cottage was just as advertised. It was nice and clean and we had a great stay there."
Charming cottage short walk to beach!
Nautical View by Bayley Vacation Rentals
Exterior

Nautical View by Bayley Vacation Rentals

10.0 out of 10, Exceptional, (18)
"Beautiful place!"
Nautical View by Bayley Vacation Rentals
Cheerful 1 bedroom cottage only 50ft from beach
Exterior

Cheerful 1 bedroom cottage only 50ft from 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."
The price is HK$2,112
HK$3,090 total
includes taxes & fees
2 Sept - 3 Sept
Cheerful 1 bedroom cottage only 50ft from beach
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

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

10/10 Excellent
"It was a last minute decision to stay here, and it turned out to be great. Stay was friendly breakfast was nice and hot. We would definitely stay here again. "
Dan 3-night trip
Posted 14 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between HK$1,374 and HK$2,112 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 448 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.