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Check prices for these dates

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Aug 29 - Aug 31
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Sep 5 - Sep 7
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Sep 19 - Sep 21
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Browse Select Windham Cottages

Our top choices for Windham cottages

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

9.8 out of 10, Exceptional, (7)
"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
Property grounds

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (87)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages
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, (5)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
COZY,Newly renovated,West Shores ,short walk to Nasons Beach 🏖🏠
Beach

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

9.6 out of 10, Exceptional, (82)
"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
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
The Outlet House, Comfortable Cottage
Interior

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
Interior

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

9.4 out of 10, Exceptional, (86)
"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.
Beach

Cute cottage only a 10 min walk to the beach.

10.0 out of 10, Exceptional, (11)
"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)
"Lovely cabin. "
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
Dining

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

9.2 out of 10, Wonderful, (75)
"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!
Beach

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!
Children's area

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 CA $243
CA $432 total
includes taxes & fees
Sep 1 - Sep 2
Large 2BD cottage 10 min to Pier & Beach Pets ok
The Hidden Cove by Bayley Vacation Rentals
Beach nearby

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!
Beach

3 BR Lake house in Sebago Maine steps from beach!

10.0 out of 10, Exceptional, (2)
"Great house to stay at. We had the perfect week! Huge thanks Nelson family."
3 BR Lake house in Sebago Maine steps from beach!
Charming cottage short walk to beach!
TV, fireplace

Charming cottage short walk to beach!

9.6 out of 10, Exceptional, (31)
"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
Fridge, microwave, oven, stovetop

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 CA $311
CA $473 total
includes taxes & fees
Sep 15 - Sep 16
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

La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

10/10 Excellent
"Nice and clean"
Renee 2-night trip
Posted 8 hours ago
La Quinta Inn & Suites by Wyndham Portland