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
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Bailey Island holiday homes

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 HK$969
HK$1,227 total
includes taxes & fees
7 Jul - 8 Jul
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 HK$1,098
HK$1,368 total
includes taxes & fees
28 Jul - 29 Jul
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
TV, offices

Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
Fully Updated Airy Historic Home in South Freeport
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is HK$1,647
HK$2,881 total
includes taxes & fees
7 Jul - 8 Jul
Camp Forever cottage
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 HK$1,441
HK$2,364 total
includes taxes & fees
6 Jul - 7 Jul
Mid Coast Getaway w/ water views
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 HK$1,588
HK$2,885 total
includes taxes & fees
6 Jul - 7 Jul
Full sized home
Terrace/patio

•Peaceful Private Freeport 2 BR Home on the Ocean•

•Peaceful Private Freeport 2 BR Home on the Ocean•
Freeport
The price is HK$2,476
HK$5,485 total
includes taxes & fees
8 Jul - 9 Jul
•Peaceful Private Freeport 2 BR Home on the Ocean•
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 HK$2,314
HK$3,744 total
includes taxes & fees
19 Jul - 20 Jul
Centerview cottage
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 HK$2,470
HK$3,708 total
includes taxes & fees
14 Jul - 15 Jul
2 bedroom w/ expansive water views
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 HK$2,039
HK$3,984 total
includes taxes & fees
21 Jul - 22 Jul
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Exterior detail

30 Acres with Woodland Trails and Playground

30 Acres with Woodland Trails and Playground
Freeport
10.0 out of 10, Exceptional, (1 review)
"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "
United States
Zoraida
30 Acres with Woodland Trails and Playground
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 HK$1,605
HK$1,980 total
includes taxes & fees
6 Jul - 7 Jul
Captain's 2BR Suite. Best value, near everything, big yard, treehouse. No fees.
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 HK$2,385
HK$5,967 total
includes taxes & fees
9 Jul - 10 Jul
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
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 HK$2,389
HK$3,993 total
includes taxes & fees
9 Jul - 10 Jul
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
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 HK$2,863
HK$6,908 total
includes taxes & fees
8 Jul - 9 Jul
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
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 HK$3,169
HK$4,523 total
includes taxes & fees
4 Jul - 5 Jul
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
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 HK$3,529
HK$5,343 total
includes taxes & fees
23 Jul - 24 Jul
Award Winning Luxury Carriage House a short stroll from town!
Interior

Classic Maine Waterfront Home on the Back River – Trevett

Classic Maine Waterfront Home on the Back River – Trevett
Boothbay
Classic Maine Waterfront Home on the Back River – Trevett
Aerial view

Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
The price is HK$2,805
HK$6,742 total
includes taxes & fees
6 Jul - 7 Jul
Three bedroom in United States of America, Freeport
Exterior

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (10 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is HK$4,706
HK$7,630 total
includes taxes & fees
9 Jul - 10 Jul
Willard Square Family Home
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

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

10/10 Excellent
"Staff very helpful. Breakfast not great"
Eugenia 1-night trip
Posted 1 hour ago
Comfort Inn South Portland Airport

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
297
Accommodation
564 Vacation Homes
Lowest Price
HK$1,227
Highest Price
HK$7,630

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