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
Book a stay at this family-friendly vacation home in Cumberland Center. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Capt Lyman Stuart, ...
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
Book a stay at this family-friendly vacation home in Portland. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Thompson's Point and ...
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
Stay at this vacation home in Portland. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Thompson's Point and Maine Mall are located ...
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
Book a stay at this family-friendly vacation home in Boothbay Harbor. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Boothbay Harbor ...
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
Book a stay at this beach vacation home in Boothbay Harbor. Enjoy a beach locale, a garden, and patios. Our guests praise the helpful staff in our reviews. Popular ...
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
Book a stay at this family-friendly vacation home in Bailey Island. Enjoy free WiFi, a garden, and patios. Popular attractions Bailey Island Bridge and Cobwork ...
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
Stay at this vacation home in East Boothbay. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Grimes Cove Beach and Linekin Bay are located ...
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
Stay at this vacation home in Boothbay Harbor. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Fisherman's Memorial Park and Burnt Island ...
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 NZ$1,218 per night from 24 Apr to 25 Apr
NZ$1,218
includes taxes & fees
24 Apr - 25 Apr
Book a stay at this family-friendly vacation home in Freeport. Enjoy free WiFi, a garden, and patios. Popular attractions Desert of Maine and Wilbur's of Maine ...
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
NZ$161
Highest Price
NZ$1,218
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

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 NZ$179 per night from 4 May to 5 May
NZ$179
includes taxes & fees
4 May - 5 May
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the restaurant and the helpful staff ...
Ramada Plaza 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 NZ$342 per night from 20 Apr to 21 Apr
NZ$342
includes taxes & fees
20 Apr - 21 Apr
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
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 NZ$289 per night from 13 Apr to 14 Apr
NZ$289
includes taxes & fees
13 Apr - 14 Apr
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
Cambria Hotel Portland Downtown-Old Port
Save an average of 15% on thousands of hotels when you're signed in
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$161 per night from 7 Apr to 8 Apr
NZ$161
includes taxes & fees
7 Apr - 8 Apr
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Clarion Hotel Portland
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.