Book Holiday Homes in Bailey Island
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Bailey Island

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

Shady Potts Point Cottage Cooled by Ocean Breezes

Sunny Modern Oasis in Portland’s Trendy East End

On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Elegant and efficient Island home 4 miles from downtown Portland

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

Fantastic Waterfront Views
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 | 581 Holiday Homes |
---|---|
Lowest Price | NZ$196 |
Highest Price | NZ$845 |
Popular accommodation | Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor, Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!, Shady Potts Point Cottage Cooled by Ocean Breezes , Sunny Modern Oasis in Portland’s Trendy East End, On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing., Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary, Elegant and efficient Island home 4 miles from downtown Portland, Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, Fantastic Waterfront Views |
More accommodations in Bailey Island
Top trending hotels in Bailey Island

Days Inn by Wyndham Airport/Maine Mall

Germaine Inn South Portland

Ramada Plaza by Wyndham Portland

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