Bailey Island which includes a bay or harbour

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Browse Select Great Island Holiday Homes

Relax on the deck with Adirondack chairs, enjoy a cozy fireplace, and unwind in a serene natural setting.

"Very clean and had everything we needed for a nice long weekend with our pup in Boothbay Harbor"

Enjoy a clean, contemporary kitchen with a large window offering a view of the surrounding landscape.

"Beautiful location, comfortable beds and wonderful linens. This place was wonderful"

"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."

includes taxes & fees

7 Aug - 8 Aug

includes taxes & fees

24 Aug - 25 Aug

"We could not have been more pleased with our experience. Not only is the home beautiful and cozy, but the attention to detail is beyond any expectations. The entire process was smooth as could be and the property was an excellent base for our visit to the area. Everything was considered - more amenities than you would imagine and also completely top notch. Excellent views, comfortable beds, luxurious towels, fully appointed kitchen, etc. We felt so lucky to be there."

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!"

Relax in a comfortable bedroom with a plush sofa, decorative headboard, and a cozy rug.

"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "

Relax on the waterfront deck with Adirondack chairs and a small table, taking in the view of the nearby cruise ship.

"We loved our stay here. Everything was clean. My kids loved the toy blocks and running out on the beach. There is a playground nearby on the beach. Views are amazing and the area is very quiet. Great vacation!"

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!"

Enjoy cooking and dining in this well-equipped kitchen with a central island and dining area.

"A nice, quiet location that is just a walk away from a pretty town, and not too far of a drive away from many great places to visit along the coastline."

Enjoy meals in the kitchen with a dining table and benches, and access to a staircase leading to the upper level.

"Just as advertised, would definitely stay here again. Great location!"

Relax in this spacious living room with a high ceiling, large windows, and a cozy fireplace.

"Your home is beautiful!! Love all the windows, very comfortable!!"

Enjoy cooking in this well-lit kitchen with ample workspace and a large island.

"Super clean and excellent location with a view."

3 bedrooms, iron/ironing board, travel cot, free WiFi

"Wonderful place to stay provided so many amenities. Beautiful views of Curtis Bay. Would definitely come back! "

Set amidst lush greenery, this traditional building features a gabled roof and a serene natural setting.

"Wooded setting is very nice and quiet in a well maintained house. Convenient to Boothbay Harbor, East Boothbay, and Maine Botanical Gardens. A list of nearby hiking trails would be useful. Lots of nearby restaurants. We liked Shannon's Unshelled, Thistle Inn, and Carriage House. Linekin/Burley hike was rugged but very good on Ocean Point Rd."

Enjoy meals in this dining area with a glass-top table and comfortable seating.

"Our family enjoyed our stay at this home in Bath, ME The host was very kind and helpful!"

Enjoy the serene garden surroundings and outdoor space.

"We thoroughly enjoyed our stay at the Portland Cottage! It was a wonderful location, extremely clean, and incredible cozy. Paul is a delightful host!"