Experience Small-town Maine Living in Bailey Island Rentals

Bailey Island, Maine is a wonderful summer getaway destination for families and couples alike. Here, you’ll find the comfort of home in Bailey Island rentals and plenty of fun in the sun with access to neighboring Orr Island, too.

Stay in Bailey Island Rentals for a Cozy Getaway


Several Bailey Island vacation rentals have been touted for their attention to detail and rustic décor made to make visitors feel welcome. Schedule a short weekend away with your sweetie, and take advantage of the nearly world-famous seafood at one of the local restaurants, too. Choose Bailey Island, ME rentals on the beach for a romantic evening walk, or relax while watching the sunset together.

Day Trips from Bailey Island Vacation Rentals


Since the construction of the Cobwork Bridge, which connects Bailey Island to Orr Island, the choices in things to do here have literally become endless. Since you most likely will drive to stay in Bailey Island rentals, simply hop in the car and explore an additional island that offers Maine’s best food and attractions.

Bailey Island vacation rentals are also located near The Giant Steps, an interesting rock formation that looks much like a flight of stairs on the edge of the island. Bailey Island, ME rentals demand a visit to Mackerel Cove, as this is known as one of the top-photographed locations in Maine.

Access Local Beaches near Bailey Island ME Rentals


Your entire group will love a day at Land’s End, a famous beach located near Bailey Island rentals. This is an ideal location, as Bailey Island vacation rentals are located in an area famous for rocky beaches. Birds and other wildlife reside here, and you’ll find plenty of photo opportunities during mating and migrating seasons. Your choice in Bailey Island, ME rentals offers access to a multitude of activities and natural attractions the entire family can enjoy during your stay.

Still searching for the perfect vacation rental in the Portland and Casco Bay area? Consider staying in rentals in Brunswick, Cape Elizabeth rentals, Freeport vacation rentals, Harpswell lodging, Orr's Island rentals, rental lodging in Phippsburg, Popham Beach rentals, or rentals in Portland.

Use filters to narrow your search results!

Bailey Island: Cottages, Houses & More(44)

44 Results
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
#465503vb
(6)
2 - 7 night minimum stay
  • 4 BR,
  • 5 BA,
  • Sleeps 12
#299567
(9)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
#318909vb
(19)
  • 7 BR,
  • 4 BA,
  • Sleeps 18
#120204
(14)
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
#3001385
(7)
7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 8
#232029
(9)
4 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 11
#3579815
2 Reviews
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
#164879
2 Reviews
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
#962008
(9)
2 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
#287769
(15)
3 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 6
#184120
(4)
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
#140223
(3)
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
#229351
2 Reviews
$1,300 - $2,000
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 7
#106396
(12)
3 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
#3697949
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
#116337
(14)
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 7
#3714547
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
#116191
4 - 31 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
#940196
(4)
7 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 3
#118009
(37)
7 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 3
#175535
(9)
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
#114948
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 14
#112112
1 Review
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
#236595
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
#104516
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 17
#110724
1 Review
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 3
#242266
(3)
17 more choices from the HomeAway Network
3 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
#461438vb
1 Review
  • 2 BR,
  • Sleeps 4
#422689vb
(8)
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
#511559vb
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