Book Holiday Homes in Bailey Island

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Featured Holiday Homes in Bailey Island

Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views

Harpswell ME
Located in Harpswell, this vacation home is a 1-minute drive from Casco Bay and 7 minutes from Androscoggin River.
Opens in a new windowBeautiful Oceanfront House- Stunning Water Views
Boothbay Harbor Woodland Retreat

Boothbay Harbor Woodland Retreat

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute drive of Boothbay Harbor Marina and Burnt Island Living Lighthouse.
Opens in a new windowBoothbay Harbor Woodland Retreat
Centerview cottage

Centerview cottage

Harpswell ME
The price is AU$675 per night from 25 May to 26 May
AU$675
25 May - 26 May
includes taxes & fees
Located in Harpswell, this vacation home is by the ocean, a 1-minute drive from Casco Bay and 9 minutes from Paddleworks.
Opens in a new windowCenterview cottage
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5 Star Back Cove Apartment with water view!

5 Star Back Cove Apartment with water view!

Portland ME
With a stay at this vacation home in Portland (Back Cove), you'll be within a 5-minute drive of Thompson's Point and Casco Bay.
Opens in a new window5 Star Back Cove Apartment with water view!
Downtown Waterfront Cottage with shoreline sitting room

Downtown Waterfront Cottage with shoreline sitting room

Boothbay Harbor ME
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by ...
Opens in a new windowDowntown Waterfront Cottage with shoreline sitting room
Rare West End Home • Walk to Old Port, Harbor View

Rare West End Home • Walk to Old Port, Harbor View

Portland ME
With a stay at this vacation home in Portland (West End), you'll be within a 5-minute drive of Thompson's Point and Victoria Mansion.
Opens in a new windowRare West End Home • Walk to Old Port, Harbor View
Captain's Guest Room. Discover the authenticity & great value!

Captain's Guest Room. Discover the authenticity & great value!

Bath ME
The price is AU$178 per night from 24 May to 25 May
AU$178
24 May - 25 May
includes taxes & fees
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church Arts Center and Bath Center for the Arts.
Opens in a new windowCaptain's Guest Room. Discover the authenticity & great value!
Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Phippsburg ME
A stay at this vacation home places you in the heart of Phippsburg, a 1-minute drive from Casco Bay and 7 minutes from Maine Maritime Museum.
Opens in a new windowSummer 2026 ! Kayak on the Kennebec " EVERYTHING you need "
Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute walk of Opera House at Boothbay Harbor and Boothbay Region Historical Society ...
Opens in a new windowBoothbay Harbor, 2-Story Cottage, downtown
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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
545 Holiday Homes
Lowest Price
AU$178
Highest Price
AU$675
Popular accommodation
Beautiful Oceanfront House- Stunning Water Views, Boothbay Harbor Woodland Retreat, Centerview cottage, 5 Star Back Cove Apartment with water view!, Downtown Waterfront Cottage with shoreline sitting room, Rare West End Home • Walk to Old Port, Harbor View, Captain's Guest Room. Discover the authenticity & great value!, Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need ", Boothbay Harbor, 2-Story Cottage, downtown

Top trending hotels in Bailey Island

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$340 per night from 25 May to 26 May
AU$340
25 May - 26 May
includes taxes & fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 5-minute drive of Thompson's Point and Fore Street Gallery.
Opens in a new windowPortland Harbor Hotel
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
The price is AU$249 per night from 26 May to 27 May
AU$249
26 May - 27 May
includes taxes & fees
With a stay at Portland Regency Hotel & Spa, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Fore Street Gallery.
Opens in a new windowPortland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is AU$296 per night from 25 May to 26 May
AU$296
25 May - 26 May
includes taxes & fees
With a stay at Cambria Hotel Portland Downtown-Old Port in Portland (Downtown Portland), you'll be within a 10-minute drive of Thompson's Point and Maine Jewish ...
Opens in a new windowCambria Hotel Portland Downtown-Old Port
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HomeAwhile

HomeAwhile

2 out of 5
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 26 May to 27 May
AU$191
26 May - 27 May
includes taxes & fees
With a stay at HomeAwhile in Scarborough, you'll be near the airport, within a 10-minute drive of Thompson's Point and Maine Mall.
Opens in a new windowHomeAwhile
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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.