Book Holiday Homes in Bailey Island

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Featured Holiday Homes in Bailey Island

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cumberland
With a stay at this vacation home, you'll be centrally located in Cumberland Center, within a 15-minute drive of Thompson's Point and Casco Bay.
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
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, within a 10-minute drive of Thompson's Point and Maine Mall.
The Globe House on Munjoy Hill - Walk to Breweries
Rent a room in the gorgeous Holt House

Rent a room in the gorgeous Holt House

Portland
With a stay at this vacation home in Portland (Parkside), you'll be a 3-minute drive from Thompson's Point and 8 minutes from Maine Mall.
Rent a room in the gorgeous Holt House
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Beautifully renovated home w/ prime location - walk to the footbridge & downtown

Beautifully renovated home w/ prime location - walk to the footbridge & downtown

Boothbay Harbor
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 4-minute walk from Fisherman's Memorial Park and 8 minutes by foot ...
Beautifully renovated home w/ prime location - walk to the footbridge & downtown
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
With a stay at this vacation home in Boothbay Harbor, you'll be on the beach, just a 4-minute walk from Boothbay Harbor Memorial Library and 6 minutes by foot ...
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
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
Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Boothbay
With a stay at this vacation home in East Boothbay (Ocean Point), you'll be a 4-minute walk from Linekin Bay and 11 minutes by foot from Grimes Cove Beach.
Welcome to Owl House - Your Coastal Retreat in East Boothbay!
Ambleside- a beautifully renovated home in Boothbay Harbor Maine!

Ambleside- a beautifully renovated home in Boothbay Harbor Maine!

Boothbay Harbor
When you stay at this vacation home in Boothbay Harbor, you'll be by the sea, within a 15-minute walk of Fisherman's Memorial Park and Linekin Bay.
Ambleside- a beautifully renovated home in Boothbay Harbor Maine!
Spacious Country Home Freeport, Only 5 min to LL Bean!

Spacious Country Home Freeport, Only 5 min to LL Bean!

Freeport
The price is AU$1,129 per night from 24 Apr to 25 Apr
AU$1,129
includes taxes & fees
24 Apr - 25 Apr
With a stay at this vacation home in Freeport, you'll be by the sea, within a 10-minute drive of LL Bean Flagship Store and Casco Bay.
Spacious Country Home Freeport, Only 5 min to LL Bean!
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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
534 Holiday Homes
Lowest Price
AU$148
Highest Price
AU$1,129
Popular accommodation
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, The Globe House on Munjoy Hill - Walk to Breweries, Rent a room in the gorgeous Holt House, Beautifully renovated home w/ prime location - walk to the footbridge & downtown, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary, Welcome to Owl House - Your Coastal Retreat in East Boothbay! , Ambleside- a beautifully renovated home in Boothbay Harbor Maine!, Spacious Country Home Freeport, Only 5 min to LL Bean!

Top trending hotels in Bailey Island

La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

2.5 out of 5
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$148 per night from 7 Apr to 8 Apr
AU$148
includes taxes & fees
7 Apr - 8 Apr
Located in Portland, La Quinta Inn & Suites by Wyndham Portland is a 5-minute walk from Portland Exposition Building and 5 minutes by foot from Hadlock ...
La Quinta Inn & Suites by Wyndham Portland
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$312 per night from 6 Apr to 7 Apr
AU$312
includes taxes & fees
6 Apr - 7 Apr
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$265 per night from 10 Apr to 11 Apr
AU$265
includes taxes & fees
10 Apr - 11 Apr
Located in Portland (East Bayside), Cambria Hotel Portland Downtown-Old Port is within a 10-minute drive of Thompson's Point and Maine Mall.
Cambria Hotel Portland Downtown-Old Port
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Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$266 per night from 21 Apr to 22 Apr
AU$266
includes taxes & fees
21 Apr - 22 Apr
With a stay at Canopy by Hilton Portland Waterfront in Portland (Downtown Portland), you'll be a 5-minute drive from Thompson's Point and 9 minutes from Maine ...
Canopy by Hilton Portland Waterfront
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.