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Our top choices for Bailey Island vacation homes

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is ¥14,942
¥31,938 total
includes taxes & fees
Jan 21 - Jan 22
Escape to Positive Outlook

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
2.0 star property
Brunswick
10.0 out of 10, Exceptional, (1 review)
"This house was clean and just as described! Close to campus and downtown. Our host was responsive and very helpful!"
United States
Erin B.
The price is ¥24,509
¥68,079 total
includes taxes & fees
Feb 1 - Feb 2
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14 reviews)
"it's a beautiful property and the owner was very helpful in our times of need."
United States
ROSEMARY A.
The price is ¥16,610
¥38,407 total
includes taxes & fees
Jan 26 - Jan 27
Fantastic Waterfront Views

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is ¥20,556
¥54,463 total
includes taxes & fees
Jan 26 - Jan 27
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (38 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is ¥25,144
¥52,410 total
includes taxes & fees
Jan 21 - Jan 22
Modern & Sunny House Steps from the Promenade. Private Parking!

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (50 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is ¥28,462
¥53,946 total
includes taxes & fees
Feb 2 - Feb 3
Full sized home

Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
2.0 star property
Munjoy Hill
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely fantastic stay! The house is clean, comfortable and has all the amenities to stay in. However with such a great location to all that Portland has to offer taking a quick walk to whatever strikes your fancy is highly recommended. The bakery on the corner has great coffee and baked goods. We didn’t need much from Doug but when I messaged him he was very responsive and accommodating. The beds are extremely comfortably. The location is quiet, within walking distance or a quick uber...
United States
Carl K.
The price is ¥23,064
¥54,624 total
includes taxes & fees
Jan 29 - Jan 30
Chic 3-bedroom house in Munjoy Hill with off-street parking.

Entire ideally located home in Cape Elizabeth’s coveted seaside community

Entire ideally located home in Cape Elizabeth’s coveted seaside community
Cape Elizabeth
10.0 out of 10, Exceptional, (4 reviews)
"The host was welcoming and it was an easy and smooth check in and check out process. Place was a great spot for my friends and I during our stay for a pond hockey tournament."
United States
Kerry W.
The price is ¥25,684
¥60,756 total
includes taxes & fees
Jan 25 - Jan 26
Entire ideally located home in Cape Elizabeth’s coveted seaside community

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is ¥31,638
¥60,020 total
includes taxes & fees
Feb 2 - Feb 3
Modern Getaway by the Sea

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
2.0 star property
Georgetown
The price is ¥23,566
¥48,524 total
includes taxes & fees
Jan 29 - Jan 30
Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is ¥22,147
¥36,210 total
includes taxes & fees
Jan 21 - Jan 22
Charming 1-bedroom ADU in wonderful Portland neighborhood

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

Spacious Country Home Freeport, Only 5 min to LL Bean!
Freeport
9.8 out of 10, Exceptional, (16 reviews)
"It was a very relaxing house to stay in. Everything was provided in the kitchen, bathroom and bedrooms. Lots of room for all of us to mingle. "
United States
Carla S.
The price is ¥23,096
¥72,976 total
includes taxes & fees
Jan 21 - Jan 22
Spacious Country Home Freeport, Only 5 min to LL Bean!

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
9.0 out of 10, Wonderful, (25 reviews)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is ¥22,137
¥59,978 total
includes taxes & fees
Jan 21 - Jan 22
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Modern Cottage with Peeks of Ocean Views

Modern Cottage with Peeks of Ocean Views
Cape Elizabeth
10.0 out of 10, Exceptional, (1 review)
"Very cute property, perfect location! Had every amenity we could possibly need. The home was decorated so cutely and the shower was AMAZING! I’m coming back just for the shower! "
United States
Christina S.
The price is ¥45,064
¥69,321 total
includes taxes & fees
Feb 1 - Feb 2
Modern Cottage with Peeks of Ocean Views

Generous Living in a Warm, Welcoming Home

Generous Living in a Warm, Welcoming Home
Topsham
The price is ¥15,572
¥68,357 total
includes taxes & fees
Jan 22 - Jan 23
Generous Living in a Warm, Welcoming Home

Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
2.0 star property
Bath
10.0 out of 10, Exceptional, (9 reviews)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is ¥67,201
¥101,515 total
includes taxes & fees
Jan 22 - Jan 23
Award Winning Luxury Carriage House a short stroll from town!

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
The price is ¥56,923
¥179,245 total
includes taxes & fees
Jan 21 - Jan 22
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
South Portland
10.0 out of 10, Exceptional, (1 review)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is ¥37,016
¥105,180 total
includes taxes & fees
Jan 26 - Jan 27
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very Good, (58 reviews)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is ¥22,247
¥47,861 total
includes taxes & fees
Jan 21 - Jan 22
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
8.8 out of 10, Excellent, (3 reviews)
"Great location"
United States
Mark J.
The price is ¥23,406
¥62,757 total
includes taxes & fees
Jan 21 - Jan 22
The 87th Townhome - Local Landmark
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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Top Bailey Island Hotel Reviews

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
220
Accommodation
509 Vacation Homes
Lowest Price
¥36,210
Highest Price
¥179,245