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Our top choices for Bailey Island vacation homes
Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (2)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
Gregory M.
The price is AED 347
AED 742 total
includes taxes & fees
10 Dec - 11 Dec
The Outlet Studio, Rustic Comfort w Fireplace
Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
Deanna S.
The price is AED 298
AED 585 total
includes taxes & fees
10 Dec - 11 Dec
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5)
"Great place for our family to stay while visiting the Maine coast."
Craig C.
The price is AED 514
AED 1,305 total
includes taxes & fees
21 Dec - 22 Dec
Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
Heather S.
The price is AED 771
AED 1,368 total
includes taxes & fees
5 Jan - 6 January 2026
Huge Historic Downtown Townhome
West End
9.8 out of 10, Exceptional, (8)
"The house is so charming and in an excellent location! It is walking distance to many options, on a quiet, beautiful street with comfortable beds and a well appointed kitchen. Easy booking and communication throughout! "
Siobhain C.
The price is AED 651
AED 1,694 total
includes taxes & fees
8 Jan - 9 January 2026
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
8.8 out of 10, Excellent, (23)
"Nice place, I'd stay again!"
Ronnie C.
The price is AED 496
AED 1,401 total
includes taxes & fees
10 Dec - 11 Dec
Spacious Portland Home + Parking
Parkside
9.0 out of 10, Wonderful, (2)
"we used the house has home base for several outings in Portland. Great location and easy parking."
Ellen M.
The price is AED 606
AED 2,130 total
includes taxes & fees
10 Dec - 11 Dec
Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58)
"Most enjoyed vacation this year.Location was beautiful. "
Debra S.
The price is AED 771
AED 1,333 total
includes taxes & fees
31 Dec - 1 January 2026
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.
Top Bailey Island Hotel Reviews
Clarion Hotel Portland Airport ME
10/10 Excellent
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