Book Holiday Homes in Bailey Island

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Featured Holiday Homes in Bailey Island

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by foot from Boothbay Harbor ...
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Captain's Quarters  Guest Room w/Private Bath & Entrance. Best Value in Town!

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

Bath
The price is AU$254 per night from 13 Aug to 14 Aug
AU$254
13 Aug - 14 Aug
includes taxes & fees
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church and Markings Gallery.
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
Shady Potts Point Cottage Cooled by Ocean Breezes

Shady Potts Point Cottage Cooled by Ocean Breezes

Harpswell
With a stay at this vacation home in Harpswell, you'll be by the sea, just steps from Casco Bay and a 3-minute drive from Ash Cove Pottery.
Shady Potts Point Cottage Cooled by Ocean Breezes
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Sunny Modern Oasis in Portland’s Trendy East End

Sunny Modern Oasis in Portland’s Trendy East End

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.
Sunny Modern Oasis in Portland’s Trendy East End
On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.

On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.

Phippsburg
Located in Phippsburg, this vacation home is by the ocean, a 1-minute drive from Casco Bay and 6 minutes from Popham Beach State Park.
On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.
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
Elegant and efficient Island home 4 miles from downtown Portland

Elegant and efficient Island home 4 miles from downtown Portland

Portland
With a stay at this vacation home in Portland, you'll be steps from Casco Bay and a 3-minute drive from Little Diamond Island.
Elegant and efficient Island home 4 miles from downtown Portland
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 LL Bean Flagship ...
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Fantastic Waterfront Views

Fantastic Waterfront Views

Phippsburg
The price is AU$877 per night from 17 Aug to 18 Aug
AU$877
17 Aug - 18 Aug
includes taxes & fees
With a stay at this vacation home in Phippsburg (West Point), you'll be within a 15-minute drive of Casco Bay and Popham Beach State Park.
Fantastic Waterfront Views
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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
583 Holiday Homes
Lowest Price
AU$162
Highest Price
AU$877
Popular accommodation
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor, Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!, Shady Potts Point Cottage Cooled by Ocean Breezes , Sunny Modern Oasis in Portland’s Trendy East End, On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing., Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary, Elegant and efficient Island home 4 miles from downtown Portland, Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, Fantastic Waterfront Views

Top trending hotels in Bailey Island

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$194 per night from 25 Aug to 26 Aug
AU$194
25 Aug - 26 Aug
includes taxes & fees
When you stay at Days Inn by Wyndham Airport/Maine Mall in South Portland, you'll be in a shopping district, a 2-minute drive from Maine Mall and 8 minutes from ...
Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is AU$162 per night from 24 Aug to 25 Aug
AU$162
24 Aug - 25 Aug
includes taxes & fees
With a stay at Germaine Inn South Portland in South Portland, you'll be a 4-minute drive from Maine Mall and 6 minutes from Thompson's Point.
Germaine Inn South Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$219 per night from 1 Sept to 2 Sept
AU$219
1 Sept - 2 Sept
includes taxes & fees
Located in Portland (Nasons Corner), Ramada Plaza by Wyndham Portland is within a 10-minute drive of Maine Mall and Thompson's Point.
Ramada Plaza by Wyndham Portland
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Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$239 per night from 1 Sept to 2 Sept
AU$239
1 Sept - 2 Sept
includes taxes & fees
When you stay at Comfort Inn Airport in South Portland, you'll be in a shopping district, a 1-minute drive from Maine Mall and 6 minutes from Thompson's ...
Comfort Inn Airport
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.