Bailey Island showing a house and rocky coastline

Holiday Homes in Bailey Island

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In one month

In two months

In three months

Featured Holiday Homes in Bailey Island and around

"Beautiful views, very clean and enjoyed the oceanside vibe both inside and out! Easy walk to general store and walkable to Giant Stairs trail and Cedar Beach."

"Connie and Mike are great hosts. The camp was clean and air conditioned! The view from camp was beautiful. The dock was amazing. "

includes taxes & fees

14 Oct - 15 Oct

"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."

"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!"

"I visited Maine with several family members. We stayed in this lovely home and used it as a homebase. It is very well located and quite nicely equipped. "

"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "

includes taxes & fees

8 Oct - 9 Oct

"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."

"Wonderful all around"

"Great view, nice property, cool area in Harpswell. Great to stay at if you are in town for Live Well Farm. Lots of rooms, beds, and privacy. "

"Convenient location to downtown. Views are superb of the harbor. Quiet neighborhood.The kitchen is not very well equipped, but we survived. Need additional silverware, plates, etc.."

"Perfect accommodation for extended family to get together for a long weekend. House was comfortable and well-appointed with plenty of space, beds, towels etc. Air conditioning worked perfectly when needed."

includes taxes & fees

8 Oct - 9 Oct

"I stayed here for a weekend with a group of friends and it was a dream! So lovely!"

"An ideal home away from home at our most favorite place in Maine. Plenty of extra touches to make guests feel welcome and comfortable. Owner is quick to respond to any questions, and went well above-and-beyond to help us out when we experienced an unforeseen situation. I am so very grateful! I hope we can book this wonderful home again next summer. Thank you!"

"The cottage is just lovely, very “Maine”, newly redone and extremely comfortable. Communication with the host was easy. We thoroughly enjoyed our stay."

"Fantastic coastal cottage feel! Beautiful view of the the bay. Updated bathrooms and kitchen. Perfect location to walk to center of Boothbay harbor shops and restaurants. My only suggestion...replace any bad window shades with working ones..andCheck all ac unit filters.maybe consider updating the upstairs ac units.We had an amazing time."

"The house was the perfect size for my family of 7 adults. We enjoyed the short walk to downtown Boothbay too."

"Beautiful property with plenty of room for our family of 6."

"Cute neighborhood. Very quiet. I do have a couple things that wasn’t very pleasant…there was a loofa with hair left in the shower. Nothing felt clean. The rug was dirty in the back sitting room. It was very very hot . There was nowhere to put the trash because the trash was full outside. A lock should be on cellar door. Owner was very easy yo deal with. "