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

Peaceful Lake waterfront! Full Kitchen! Heat&AC! 5min to town, 8min to Garden!

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Sunny Modern Oasis in Portland’s Trendy East End

Full sized home

The Globe House on Munjoy Hill - Walk to Breweries

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Spacious 4-bedroom house located in the heart of Portland, ME.
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 | 509 Holiday Homes |
|---|---|
Lowest Price | NZ$140 |
Highest Price | NZ$1,810 |
Popular accommodation | Peaceful Lake waterfront! Full Kitchen! Heat&AC! 5min to town, 8min to Garden!, Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port, Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!, Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome, Sunny Modern Oasis in Portland’s Trendy East End, Full sized home, The Globe House on Munjoy Hill - Walk to Breweries, New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!, Spacious 4-bedroom house located in the heart of Portland, ME. |
Top trending hotels in Bailey Island

The Westin Portland Harborview

Clarion Hotel Portland Airport ME

Portland Harbor Hotel

Holiday Inn Portland-By the Bay by IHG
More ways to explore Bailey Island
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
