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$196
Highest Price
NZ$320
Popular accommodation
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room, Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary, The Westin Portland Harborview, Portland Harbor Hotel

Top trending hotels in Bailey Island

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
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
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$196 per night from 20 Mar to 21 Mar
NZ$196
includes taxes & fees
20 Mar - 21 Mar
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
The Westin Portland Harborview
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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$320 per night from 19 Mar to 20 Mar
NZ$320
includes taxes & fees
19 Mar - 20 Mar
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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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.