Windham Vacation Rentals

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Browse Select Windham Vacation Homes

Kitchen area with microwave, toaster, refrigerator, and sink.

"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."

CA $574 total

includes taxes & fees

Aug 20 - Aug 21

Stroll along the pier, taking in the serene views of the ocean and surrounding landscape.

"Mitchells home was PERFECT.Always quick to communicate and very accommodating. If you are looking for a great place to stay I cant say enough good things. Well stocked he has thought of everything people need when away. He even has games to play which was a nice surprise. You wont regret staying bere! Thanks again so much Mitchell!!!"

"Perfect location and communication with the property manager"

Cozy attic bedroom with a large bed, nightstands, and a window above.

"The house is in a wonderful location with great views of the ocean from several rooms. The listing photos really do tell the story of this beautiful home. The beach is just a few steps away from the property. Attention to detail was obviously put in to ensure a wonderful guest experience. The home is very clean, there are practical amenities throughout (4 smart TV’s), and our host was super communicative and accommodating. Portland & Saco being a short drive away is just icing on the cake. Can’t...

CA $1,152 total

includes taxes & fees

Aug 31 - Sep 1

Enjoy a peaceful stay in this charming house with a porch, surrounded by a lush lawn and a majestic tree.

"Great stay in very clean house in a very quiet ocean side community. Perfect getaway!"

Kitchen features a stove, microwave, sink, and dishwasher, with a window offering a view of the outdoors.

"Daughter lives in area it suited us just fine."

Relax on the spacious deck with a table and chairs, taking in views of the surrounding greenery.

"This apartment was very clean, modern, and fairly private, located on a quite street, but still close enough to walk to shops, cafes, breweries. Only about half a mile from downtown. Would definitely stay again!"

Stunning two-story home surrounded by lush greenery and trees, featuring a charming front porch and symmetrical facade.

"We had a great stay! Amazing weather and plenty of lobster."

"Excellent cottage with great interior space and couldn’t ask for a better location. "

Relax in a serene lakeside setting with a clear view of the lake and a cozy outdoor seating area featuring two Adirondack chairs and a fire pit.

Enjoy meals in the kitchen with a stove and dining area featuring a table and chairs.

CA $2,998 total

includes taxes & fees

Aug 17 - Aug 18

Relax in this stylish living room with a high ceiling, comfortable sofa, and flat-screen TV.

"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"

"We enjoyed this well kept property with beautiful gardens. It was very pet friendly with a nice back yard area. We cooked steak on the grill one night."

Enjoy serene lakeside views and access to the water from this picturesque dock.

"Would stay here again. Loved the location and the size of the rooms! Perfect for a group and very pet friendly."

Enjoy cooking in this well-equipped kitchen with oven, microwave, and refrigerator.

"We really enjoyed this property. It was very clean, and very comfortable. We will visit again. "

Relax on the outdoor deck, surrounded by lush greenery and shaded by a large umbrella.

"Perfect Lakefront Getaway on Panther PondWe had a fantastic week at this beautiful lake house on Panther Pond. The home was clean, spacious, and had a great kitchen.The lake was peaceful and perfect for swimming and kayaking. We spent most days on the water and evenings grilling and relaxing by the fire pit. One enjoyable perk was the ping pong table in the basement — we had nightly tournaments that kept us entertained.The location was quiet yet close to stores and towns like Raymond and...

Relax on the porch with a round table and two Adirondack chairs, surrounded by lush greenery.

"Comfortable place to stay and enjoy time with family. We enjoyed exploring Peaks Island and Portland. Everything we needed."

Fully equipped kitchen with dishwasher, oven, refrigerator, sink, and kettle.

"This was our second stay at Beth’s home, and it certainly won’t be the last (as long as she’s willing to have us!) Everything is absolutely perfect. Beth is a thoughtful host, the location is perfect and the home is beautiful - you can’t go wrong!"