Book Holiday Homes in Bailey Island
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Featured Holiday Homes in Bailey Island

Sunny Modern Oasis in Portland’s Trendy East End

Fantastic Waterfront Views

Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Captain's Guest Room w/private bath. Walk to everything.

Large, light filled 4 bedroom house - walk to ocean and ferry

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Lone Pine Cottage Maine - Chef’s Kitchen
Bailey Island Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Bailey Island vacation homes are the perfect way for you to wing it.
Holiday houses in Bailey Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Bailey Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Bailey Island adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Bailey Island with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Bailey Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Bailey Island Holiday Homes essential information
Accommodation | 535 Holiday Homes |
|---|---|
Lowest Price | NZ$125 |
Highest Price | NZ$641 |
Popular accommodation | Sunny Modern Oasis in Portland’s Trendy East End, Fantastic Waterfront Views, Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH., Captain's Guest Room w/private bath. Walk to everything., Large, light filled 4 bedroom house - walk to ocean and ferry, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Lone Pine Cottage Maine - Chef’s Kitchen |
Top trending hotels in Bailey Island

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Tru by Hilton Portland Airport Area

Portland Harbor Hotel

Portland Regency Hotel & Spa
More ways to explore Bailey Island
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^Subject to availability and chosen travel dates.
