Search Vacation Homes in Bailey Island
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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.
$192 nightly
The price is $202
Dec 10 - Dec 11
Total with taxes and fees
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.
$146 nightly
The price is $159
Dec 10 - Dec 11
Total with taxes and fees
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.
$327 nightly
The price is $356
Dec 11 - Dec 12
Total with taxes and fees
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.
$291 nightly
The price is $308
Dec 26 - Dec 27
Total with taxes and fees
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.
$391 nightly
The price is $427
Dec 14 - Dec 15
Total with taxes and fees
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.
$350 nightly
The price is $382
Dec 10 - Dec 11
Total with taxes and fees
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.
$525 nightly
The price is $572
Dec 10 - Dec 11
Total with taxes and fees
Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58)
"Most enjoyed vacation this year.Location was beautiful. "
Debra S.
$333 nightly
The price is $363
Dec 31 - Jan 1, 2026
Total with taxes and fees
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
Find out more about Bailey Island
Bailey Island Vacation Homes information
Number of reviews | 244 |
|---|---|
Accommodation | 524 Vacation Homes |
Lowest Price | $159 |
Highest Price | $872 |
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