Book Holiday Homes in Bailey Island

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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
Holiday Homes
Lowest Price
NZ$192
Highest Price
NZ$322
Popular accommodation
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary, PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room, Portland Harbor Hotel, Holiday Inn Portland-By the Bay, an IHG Hotel

Top trending hotels in Bailey Island

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Bailey Island
Book a stay at this family-friendly vacation home in Bailey Island. Enjoy free WiFi, a garden, and patios. Popular attractions Bailey Island Bridge and Cobwork ...
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Bailey Island
Stay at this cottage in Bailey Island. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Land's End Gift Shop and Casco Bay are located ...
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$322 per night from 17 Feb to 18 Feb
NZ$322
includes taxes & fees
17 Feb - 18 Feb
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
Portland Harbor Hotel
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Holiday Inn Portland-By the Bay, an IHG Hotel

Holiday Inn Portland-By the Bay, an IHG Hotel

3 out of 5
88 Spring St, Portland, ME
Fully refundable
The price is NZ$192 per night from 5 Feb to 6 Feb
NZ$192
includes taxes & fees
5 Feb - 6 Feb
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Holiday Inn Portland-By the Bay, an IHG Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.