A rocky shoreline with a boat, a house, and a forest in the background.

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Bailey Island vacation homes

Aerial view

Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
The price is ￥51,122
￥63,658 total
includes taxes & fees
Jul 9 - Jul 10
Three bedroom in United States of America, Freeport
Outdoor dining

Captain's Guest Room. Authenticity. Value. Near everything. No fees.

Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Bath
8.2 out of 10, Very Good, (22 reviews)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
The price is ￥19,975
￥25,299 total
includes taxes & fees
Jul 2 - Jul 3
Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Property grounds

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is ￥23,054
￥28,656 total
includes taxes & fees
Jul 7 - Jul 8
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
TV

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (6 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is ￥25,474
￥45,187 total
includes taxes & fees
Jul 1 - Jul 2
Mid Coast Getaway w/ water views
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is ￥33,974
￥59,251 total
includes taxes & fees
Jun 27 - Jun 28
Camp Forever cottage
Terrace/patio

Tide Haven Cottage on Bay Point

Tide Haven Cottage on Bay Point
Georgetown
The price is ￥38,256
￥96,717 total
includes taxes & fees
Jul 1 - Jul 2
Tide Haven Cottage on Bay Point
TV

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is ￥42,467
￥66,535 total
includes taxes & fees
Jun 27 - Jun 28
2 bedroom w/ expansive water views
Desk, iron/ironing board, free WiFi, bed sheets

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
The price is ￥33,888
￥62,943 total
includes taxes & fees
Jun 28 - Jun 29
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (53 reviews)
"Wonderful stay!"
United States
Erika T.
The price is ￥32,760
￥60,044 total
includes taxes & fees
Jul 1 - Jul 2
Full sized home
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (62 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is ￥47,725
￥77,237 total
includes taxes & fees
Jun 28 - Jun 29
Centerview cottage
Interior

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Brunswick
10.0 out of 10, Exceptional, (2 reviews)
"Great location"
United States
Ashley W.
The price is ￥46,107
￥128,023 total
includes taxes & fees
Jun 28 - Jun 29
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Terrace/patio

Captain's 2BR Suite. Best value, near everything, big yard, treehouse. No fees.

Captain's 2BR Suite. Best value, near everything, big yard, treehouse. No fees.
Bath
8.8 out of 10, Excellent, (12 reviews)
"Clean rooms. Quiet location walkable to much of downtown Bath "
United States
randy k.
The price is ￥34,605
￥42,657 total
includes taxes & fees
Jul 9 - Jul 10
Captain's 2BR Suite. Best value, near everything, big yard, treehouse. No fees.
Smart TV

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 ￥39,636
￥79,177 total
includes taxes & fees
Jul 2 - Jul 3
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Terrace/patio

•Peaceful Private Freeport 2 BR Home on the Ocean•

•Peaceful Private Freeport 2 BR Home on the Ocean•
Freeport
The price is ￥57,298
￥121,706 total
includes taxes & fees
Jul 12 - Jul 13
•Peaceful Private Freeport 2 BR Home on the Ocean•
Fridge, microwave, oven, stovetop

Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
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 ￥72,801
￥109,155 total
includes taxes & fees
Jul 23 - Jul 24
Award Winning Luxury Carriage House a short stroll from town!
Smart TV

Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (1 review)
"What a beautiful home! Everything about our stay was perfect. The home has everything you could possibly need and more. My family stayed for a long weekend and everyone was so happy with the accommodations. Hoping to go back!"
United States
Lisa L.
The price is ￥71,934
￥166,931 total
includes taxes & fees
Jun 28 - Jun 29
Luxe 5 Bed/ 3 Bath with Game Room & AC
Property grounds

Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is ￥105,157
￥309,301 total
includes taxes & fees
Jun 29 - Jun 30
Classic New England Waterfront House Big Lawn Beautiful Sunrise
Fridge, microwave, oven, stovetop

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (10 reviews)
"Incredible location right in downtown Freeport, and an even better host. We will definitely be staying with Jared again."
United States
Jake P.
The price is ￥49,199
￥123,061 total
includes taxes & fees
Jul 9 - Jul 10
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Interior

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (17 reviews)
"Great stay. Alexa was a great host. Having garaged parking and the indoor pool/hot tub was perfect for our stay that coincided with a snow. Would definitely stay here again next winter."
United States
Stuart R.
The price is ￥83,721
￥152,623 total
includes taxes & fees
Jun 28 - Jun 29
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Property grounds

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is ￥72,655
￥103,705 total
includes taxes & fees
Jun 27 - Jun 28
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
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

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

10/10 Excellent
"Breakfast was excellent and overall stay pleasant. It’s a drive to Old Port."
Yoginand 2-night trip
Posted less than an hour ago
Embassy Suites by Hilton Portland Maine

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
305
Accommodation
565 Vacation Homes
Lowest Price
￥25,299
Highest Price
￥309,301