Book Holiday Homes in Bailey Island

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Featured Holiday Homes in Bailey Island

Sunny Modern Oasis in Portland’s Trendy East End

Sunny Modern Oasis in Portland’s Trendy East End

Portland ME
Stay at this holiday home in Portland. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Portland Observatory and Maine Jewish ...
Opens in a new windowSunny Modern Oasis in Portland’s Trendy East End
Fantastic Waterfront Views

Fantastic Waterfront Views

Phippsburg ME
The price is NZ$641 per night from 5 Jan to 6 Jan
NZ$641
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this holiday home in Phippsburg. Enjoy laundry facilities and an in-room coffee maker. Popular attractions Bates-Morse Mountain Conservation Area and ...
Opens in a new windowFantastic Waterfront Views
Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Boothbay Harbor ME
Stay at this holiday home in Boothbay Harbor. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the property condition in their reviews. Popular ...
Opens in a new windowNewly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.
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Captain's Guest Room w/private bath. Walk to everything.

Captain's Guest Room w/private bath. Walk to everything.

Bath ME
Stay at this holiday home in Bath. Enjoy free Wi-Fi. Popular attractions Markings Gallery and Waterfront Park are located nearby.
Opens in a new windowCaptain's Guest Room w/private bath. Walk to everything.
Large, light filled 4 bedroom house - walk to ocean and ferry

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island ME
Stay at this holiday home in Peaks Island. Enjoy a garden, laundry facilities and patios. Popular attractions Umbrella Cover Museum and Fifth Maine Museum are ...
Opens in a new windowLarge, light filled 4 bedroom house - walk to ocean and ferry
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

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

Boothbay Harbor ME
Stay at this beach holiday home in Boothbay Harbor. Enjoy a beach locale, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowDowntown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Woolwich ME
Stay at this family-friendly holiday home in Woolwich. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Waterfront Park and Markings Gallery ...
Opens in a new windowWindward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Harpswell ME
Stay at this holiday home in Harpswell. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Mitchell Field and Paddleworks are located ...
Opens in a new windowBeautiful house on the Harpswell Peninsula over looking Casco Bay
Lone Pine Cottage Maine - Chef’s Kitchen

Lone Pine Cottage Maine - Chef’s Kitchen

Bath ME
Stay at this family-friendly holiday home in Bath. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Maine Maritime Museum and Markings ...
Opens in a new windowLone Pine Cottage Maine - Chef’s Kitchen
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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.

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
535 Holiday Homes
Lowest Price
NZ$125
Highest Price
NZ$641
Popular accommodation
Sunny Modern Oasis in Portland’s Trendy East End, Fantastic Waterfront Views, Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH., Captain's Guest Room w/private bath. Walk to everything., Large, light filled 4 bedroom house - walk to ocean and ferry, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Lone Pine Cottage Maine - Chef’s Kitchen

Top trending hotels in Bailey Island

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island ME
Stay at this beach holiday home in Bailey Island. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Cobwork Bridge and Mackerel Cove are located ...
Opens in a new windowNew Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$125 per night from 11 Jan to 12 Jan
NZ$125
11 Jan - 12 Jan 2026
includes taxes & fees
Stay at this hotel in South Portland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
Opens in a new windowTru by Hilton Portland Airport Area
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$276 per night from 16 Dec to 17 Dec
NZ$276
16 Dec - 17 Dec
includes taxes & fees
Stay at this business-friendly hotel in Portland. Enjoy free Wi-Fi, 3 coffee shops/cafes and breakfast (surcharge). Our guests praise the helpful staff and the ...
Opens in a new windowPortland Harbor Hotel
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Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star spa hotel in Portland. Enjoy free Wi-Fi, a full-service spa and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowPortland Regency Hotel & Spa
Don't see what you're looking for?
See all available properties in Bailey Island
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.