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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 382 Cottages in Windham with updated reviews, rates, and availability.

2 bedroom cottage
Smart TV

2 bedroom cottage

9.6 out of 10, Exceptional, (4)
"quiet, clean, short walk to beach"
2 bedroom cottage
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior

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

9.4 out of 10, Exceptional, (28)
"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 AED 716
AED 1,221 total
includes taxes & fees
9 Jun - 10 Jun
Large 2BD cottage 10 min to Pier & Beach Pets ok
The Great Escape - Picturesque Sebago Lake
Interior

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (47)
"Property was perfect for our stay."
The Great Escape - Picturesque Sebago Lake
Sea Bisquit Cottage by the Ocean
Sun loungers, beach towels

Sea Bisquit Cottage by the Ocean

9.4 out of 10, Exceptional, (10)
"Location great, plenty of privacy and everything you need for a beach get away Will be back!"
Sea Bisquit Cottage by the Ocean
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, (27)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
The Outlet House, Comfortable Cottage
Fridge, microwave, oven, stovetop

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (39)
"We booked this to be near our daughter and grandchildren in Freeport. It is a great location, large interior, quiet location."
The Outlet House, Comfortable Cottage
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Beach

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
Beach

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

9.8 out of 10, Exceptional, (114)
"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
Charming 2-bedroom Oceanside Cottage in Old Orchard Beach
Beach

Charming 2-bedroom Oceanside Cottage in Old Orchard Beach

The price is AED 1,065
AED 2,006 total
includes taxes & fees
1 Jun - 2 Jun
Charming 2-bedroom Oceanside Cottage in Old Orchard Beach
Cute 2+ Bedroom Cottage
Fridge, microwave, oven, stovetop

Cute 2+ Bedroom Cottage

9.6 out of 10, Exceptional, (14)
"Returned this year for our 2nd stay. Clean, comfortable and quiet. Will book again!"
Cute 2+ Bedroom Cottage
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Beach

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

10.0 out of 10, Exceptional, (1)
"Boomfish Cottage is a cozy place with everything you could need . It was clean , comfy and serene . It provided the perfect calm for us during a weekend long family wedding at nearby Caswell Flower Farm . It was also easy access for an older person ( me) as well as small children and my little ShihTzu rescue dogs . My granddaughters came by and loved catching minnows in the still warm lake. Extra bonus was enjoying the peak foliage at the lake . Eric , the property manager was very communicative...
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Sea Cottage at Fortunes Rocks
On the beach

Sea Cottage at Fortunes Rocks

9.8 out of 10, Exceptional, (79)
"Enjoyed our stay."
Sea Cottage at Fortunes Rocks
Glamorous cottage-glamping at Sebago Lake
Interior

Glamorous cottage-glamping at Sebago Lake

9.8 out of 10, Exceptional, (72)
"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
Thorburn - Experience a classic ME vacation at this beautiful summer cottage
Fridge, microwave, oven, stovetop

Thorburn - Experience a classic ME vacation at this beautiful summer cottage

9.8 out of 10, Exceptional, (13)
"Absolutely loved our late summer stay at this dreamy cottage in Harpswell. The cottage reminded us of childhood summer stays in coastal New England and the nostalgia was real and definitely welcome."
Thorburn - Experience a classic ME vacation at this beautiful summer cottage
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Property grounds

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

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

10.0 out of 10, Exceptional, (32)
"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.
The Hidden Cove by Bayley Vacation Rentals
Beach nearby

The Hidden Cove by Bayley Vacation Rentals

9.8 out of 10, Exceptional, (20)
"Great stay"
The Hidden Cove by Bayley Vacation Rentals
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Miscellaneous

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

7.8 out of 10, Good, (20)
"This was a great find! Short walk to downtown, but far enough away to be away from the crowds. Perfect oasis for myself, my pregnant wife, and our dog. We would definitely stay again!"
The price is AED 588
AED 1,073 total
includes taxes & fees
2 Jun - 3 Jun
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Cottages by the Sea #1 by Bayley Vacation Rentals
On the beach

Cottages by the Sea #1 by Bayley Vacation Rentals

10.0 out of 10, Exceptional, (6)
"Clean place, had everything we needed, and can’t beat the location. Will definitely be back."
Cottages by the Sea #1 by Bayley Vacation Rentals
Quaint Cottage Just Steps From The Beach And The Saco River
Beach

Quaint Cottage Just Steps From The Beach And The Saco River

9.8 out of 10, Exceptional, (15)
"We had a very nice, clean and comfortable stay!"
Quaint Cottage Just Steps From The Beach And The Saco River
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 AED 588 and AED 1,065 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 382 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.