Book Holiday Homes in Bailey Island

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Featured Holiday Homes in Bailey Island

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Boothbay Harbor
A stay at this vacation home places you in the heart of Boothbay Harbor, within a 5-minute walk of Boothbay Region Land Trust and Boothbay Region Historical ...
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
Oceanfront Cabin-Castle in Maine Woods

Oceanfront Cabin-Castle in Maine Woods

Georgetown
Located in Georgetown, this vacation home is by the ocean, a 1-minute drive from Reid State Park and 8 minutes from Georgetown Historical Society.
Oceanfront Cabin-Castle in Maine Woods
Charming 110-year former Inn 10' from the Ocean!

Charming 110-year former Inn 10' from the Ocean!

South Portland
Located in South Portland (Willard), this vacation home is within a 10-minute drive of Portland Head Light and State Theatre.
Charming 110-year former Inn 10' from the Ocean!
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The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries

Portland
With a stay at this vacation home, you'll be centrally located in Portland, a 3-minute drive from State Theatre and 5 minutes from Thompson's Point.
The Globe House on Munjoy Hill - Walk to Breweries
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 5-minute drive of State Theatre and Thompson's Point.
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Oceanfront home & guesthouse w/ incredible ocean views, deck & location

Oceanfront home & guesthouse w/ incredible ocean views, deck & location

Boothbay
With a stay at this vacation home, you'll be centrally located in East Boothbay, just a 3-minute walk from Grimes Cove Beach and 13 minutes by foot from Linekin ...
Oceanfront home & guesthouse w/ incredible ocean views, deck & location
Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR

Harpswell
When you a stay at this vacation home in Bailey Island, you'll be on the waterfront, just steps from Casco Bay and Cobwork Bridge.
Orchid Harbor, Bailey Island 3BR
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Bailey Island
A stay at this vacation home places you in the heart of Bailey Island, steps from Casco Bay and Bailey Island Bridge.
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Beautiful, Spacious Home, minutes to the Old Port!

Beautiful, Spacious Home, minutes to the Old Port!

Portland
The price is AU$590 per night from 2 Feb to 3 Feb
AU$590
includes taxes & fees
2 Feb - 3 Feb
With a stay at this vacation home in Portland (North Deering), you'll be within a 10-minute drive of State Theatre and Thompson's Point.
Beautiful, Spacious Home, minutes to the Old Port!
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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
404 Holiday Homes
Lowest Price
AU$174
Highest Price
AU$590
Popular accommodation
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown., Oceanfront Cabin-Castle in Maine Woods, Charming 110-year former Inn 10' from the Ocean!, The Globe House on Munjoy Hill - Walk to Breweries, Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, Oceanfront home & guesthouse w/ incredible ocean views, deck & location, Orchid Harbor, Bailey Island 3BR, Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary, Beautiful, Spacious Home, minutes to the Old Port!

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
When you a stay at this cottage in Bailey Island, you'll be on the waterfront, just steps from Casco Bay and Land's End Gift Shop.
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
A stay at this vacation home places you in the heart of Bailey Island, steps from Casco Bay and Bailey Island Bridge.
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
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 AU$279 per night from 5 Feb to 6 Feb
AU$279
includes taxes & fees
5 Feb - 6 Feb
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 5-minute drive of State Theatre and Thompson's Point.
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 AU$174 per night from 3 Feb to 4 Feb
AU$174
includes taxes & fees
3 Feb - 4 Feb
With a stay at Holiday Inn Portland-By the Bay, an IHG Hotel in Portland (Downtown Portland), you'll be a 5-minute walk from State Theatre and within a 5-minute ...
Holiday Inn Portland-By the Bay, an IHG Hotel
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.

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^Subject to availability and chosen travel dates.