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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

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, (27)
"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 588
AED 1,073 total
includes taxes & fees
6 May - 7 May
Large 2BD cottage 10 min to Pier & Beach Pets ok
Charming cottage short walk to beach!
TV, fireplace

Charming cottage short walk to beach!

9.4 out of 10, Exceptional, (26)
"We had a great time on our recent stay here. short walk to the beach, quiet neighborhood. This home was fully stocked with all the amenities and truly felt like our home away from home. Check in/out was seamless and there was great communication the the host. If we ever plan to travel to the area again, we would definately stay here once more. "
Charming cottage short walk to beach!
The Renaissance - Majestic Sebago Lake panorama
Miscellaneous

The Renaissance - Majestic Sebago Lake panorama

9.4 out of 10, Exceptional, (14)
"Second time we are coming for a family holiday here and it was even better. "
The Renaissance - Majestic Sebago Lake panorama
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Terrace/patio

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (100)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
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, (136)
"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!
Cozy countryside cottage located on Crooked river in Naples Maine.
Property grounds

Cozy countryside cottage located on Crooked river in Naples Maine.

10.0 out of 10, Exceptional, (10)
"We enjoyed our stay immensely! The place is immaculate and set up perfectly ! The owners are wonderful people. Every detail was top notch!"
Cozy countryside cottage located on Crooked river in Naples Maine.
100 feet from the ocean 3 bedroom cottage 420 friendly
Interior

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"All good! "
100 feet from the ocean 3 bedroom cottage 420 friendly
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, (112)
"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
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
Lakefront Cottage - private dock, large decks, large fire pit
Property grounds

Lakefront Cottage - private dock, large decks, large fire pit

9.4 out of 10, Exceptional, (24)
"Good location "
Lakefront Cottage - private dock, large decks, large fire pit
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
Spring into Summer at Turtle Lane Cottage
Smart TV, fireplace

Spring into Summer at Turtle Lane Cottage

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay while visiting together for a sister's weekend."
Spring into Summer at Turtle Lane Cottage
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
Beach

GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗

9.8 out of 10, Exceptional, (76)
"Clean and well equipped property with a convenient location to Nassan Beach. Comfortable stay and my family had a great time. Would recommend to others."
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
15A Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Point of interest

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
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
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, (78)
"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 🏖🏠
Classic Maine Cottage with the Comforts of Home
Fridge, microwave, oven, stovetop

Classic Maine Cottage with the Comforts of Home

9.2 out of 10, Wonderful, (10)
"This property was an excellent fit for our family. Fantastic location from the beach and within walking distance to the pier. We loved the neighborhood and spending time on the front porch. The rooms were spacious and we appreciated the large beds and futon couches in the livingroom. We will be back!"
Classic Maine Cottage with the Comforts of Home
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Fridge, microwave, oven, stovetop

Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

9.8 out of 10, Exceptional, (6)
"A rustic quaint adorable house. Great views of the water--everything was on the small size, but really do you need anything more?"
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Terrace/patio

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (31)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
The Great Escape - Picturesque Sebago Lake
Interior

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (46)
"Excellent stay!"
The Great Escape - Picturesque Sebago Lake
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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Other property types in Windham

WATERFRONT ON PETTENGILL POND
Smart TV

WATERFRONT ON PETTENGILL POND

WATERFRONT ON PETTENGILL POND
The Weldon Hotel
Deluxe Suite, 2 Bedrooms | Private kitchen | Full-size fridge, microwave, oven, stovetop

The Weldon Hotel

4.0 star property
9.8 out of 10, Exceptional, (56)
"Great hotel"
The price is AED 773
AED 1,118 total
includes taxes & fees
15 May - 16 May
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (105)
"Lovely, clean & great location!"
Gorgeous ocean-front home with stunning beach views
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.