Book Holiday Homes in Bailey Island
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Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Bailey Island

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

The Globe House on Munjoy Hill - Walk to Breweries

Rent a room in the gorgeous Holt House

Beautifully renovated home w/ prime location - walk to the footbridge & downtown

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

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Ambleside- a beautifully renovated home in Boothbay Harbor Maine!

Spacious Country Home Freeport, Only 5 min to LL Bean!
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 | 534 Holiday Homes |
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Lowest Price | NZ$161 |
Highest Price | NZ$1,218 |
Popular accommodation | Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, The Globe House on Munjoy Hill - Walk to Breweries, Rent a room in the gorgeous Holt House, Beautifully renovated home w/ prime location - walk to the footbridge & downtown, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary, Welcome to Owl House - Your Coastal Retreat in East Boothbay! , Ambleside- a beautifully renovated home in Boothbay Harbor Maine!, Spacious Country Home Freeport, Only 5 min to LL Bean! |
More accommodations in Bailey Island
Top trending hotels in Bailey Island

Ramada Plaza by Wyndham Portland

Portland Harbor Hotel

Cambria Hotel Portland Downtown-Old Port

Clarion Hotel Portland
More ways to explore Bailey Island
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.