Skip to content

Holiday rentals in Bailey Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Bailey Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Sweet Retreat
SUPERHOST
Entire bungalow · 2 guests · 1 bed · 1 bathroom

Sweet RetreatThis lovely contemporary one-story home is a relaxing, unfussy place to call home for a few days (or longer). It is located within walking distance of the famous Cribstone Bridge, Orr’s Island Candy Store and two popular restaurants on Bailey Island.

Bright Island Studio Cottage
SUPERHOST
Entire house · 2 guests · 1 bed · 1 bathroom

Bright Island Studio CottageThis small, open cottage, originally a candy store, is now an open space with queen size mattress on the sleeping loft floor, full-size futon on the main level and convenient kitchen and bathroom with shower. Within easy walking distance of the current candy store, Cribstone Bridge, restaurants and a Community Remembrance Garden honoring Holocaust victims and others, including enslaved Africans. Local honoree Black Will/William “Will” Black and descendants.

Journeys End
SUPERHOST
Entire cottage · 4 guests · 1 bed · 1 bathroom

Journeys EndJourney’s End - Fully remodeled 1 bedroom house with breath taking views of the water. Located near the end of Bailey Island, this idyllic island get away is only 15 minutes from Bowdoin College, the Maine State Music Theater and other local attractions. It is a short drive to Freeport to visit the LL Bean Flagship store and only 1 hour to Portland. Enjoy the beauty of the Maine coast in this fishing community. The luxury of home with the feel of being really away from it all.

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Bailey Island holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Bailey Island

  1. Entire house
  2. Harpswell
Ocean Watch
₹12,022 per night
  1. Entire cottage
  2. Harpswell
Classic Maine Cottage with astonishing easterly views located within walking distance to Cedar Beach!
₹10,555 per night
SUPERHOST
  1. Entire flat
  2. Harpswell
Coastal Retreat - Comfortable Stay
₹11,728 per night
  1. Entire cottage
  2. Harpswell
Nautical themed Oceanfront Cottage located at the Mouth of picturesque Mackerel Cove !
₹15,540 per night
  1. Entire house
  2. Harpswell
Oceanfront Magazine Showcase Home
₹57,071 per night
  1. Entire cottage
  2. Harpswell
3 Bedroom Oceanview Cottage just steps to desirable Stovers Beach
₹16,933 per night
SUPERHOST
  1. Entire flat
  2. Orr's Island
Shore House, Posey Unit - Ocean Front Property
₹12,095 per night
  1. Entire cottage
  2. Harpswell
On Island Time Cottage
₹16,493 per night
  1. Entire apartment
  2. Harpswell
Welcome to Bailey Island Condo on Mackerel Cove!
₹12,828 per night
  1. Entire cottage
  2. Harpswell
Compass Rose Cottage
₹9,383 per night
  1. Entire cottage
  2. Harpswell
Bailey Island, Maine Rental
₹6,964 per night
  1. Entire cottage
  2. Harpswell
Couples Cottage at the head of Mackerel Cove - Enjoy your views of Mt. Washington from the Rooftop Deck!
₹10,922 per night

Nearby destinations