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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Bailey Island vacation homes

A wooden deck with outdoor seating and string lights.

1. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (62 reviews)
"Wonderful stay!"
United States
Erika T.
The price is ￥32,283
￥58,822 total
includes taxes & fees
Aug 24 - Aug 25
Full sized home
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

2. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is ￥25,109
￥43,497 total
includes taxes & fees
Sep 16 - Sep 17
Mid Coast Getaway w/ water views
A lakeside property with a deck, picnic table, and barbecue grill.

3. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (63 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is ￥33,478
￥58,560 total
includes taxes & fees
Aug 30 - Aug 31
Camp Forever cottage
A treehouse with a wooden staircase and a small building with a colorful mural.

4. Captain's Guest Room. Authenticity. Great Value. Walk to everything.

Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Bath
8.4 out of 10, Very Good, (27 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is ￥18,174
￥28,672 total
includes taxes & fees
Sep 1 - Sep 2
Captain's Guest Room. Authenticity. Great Value. Walk to everything.
A wooden deck with a view of a lake, surrounded by trees and shrubs.

5. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (67 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 ￥47,029
￥76,110 total
includes taxes & fees
Aug 29 - Aug 30
Centerview cottage
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

6. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (4 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 ￥36,826
￥57,831 total
includes taxes & fees
Sep 16 - Sep 17
2 bedroom w/ expansive water views
A lush garden with a hammock, a variety of flowers, and a lake in the background.

7. 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 ￥95,652
￥301,140 total
includes taxes & fees
Sep 8 - Sep 9
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A cozy living room with a wooden ceiling, large windows, a rocking chair, and a bookshelf.

8. Cozy and charming coastal retreat

Cozy and charming coastal retreat
West Point
9.8 out of 10, Exceptional, (33 reviews)
"My family and I had an amazing time at the schoolhouse. It is much bigger than the pictures show! Great beds, the couches will force you to nap, and we had so much fun exploring the area. They had everything you need for fun at the beach, and lots of options for kids to keep busy. Highly recommend!"
United Kingdom
Byrony S.
Cozy and charming coastal retreat
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

9. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (17 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is ￥50,217
￥73,805 total
includes taxes & fees
Sep 9 - Sep 10
Fantastic Waterfront Views
A wooden staircase with a wooden railing, surrounded by green foliage.

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

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
8.0 out of 10, Very Good, (17 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is ￥21,203
￥26,587 total
includes taxes & fees
Aug 30 - Aug 31
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

11. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is ￥61,377
￥92,574 total
includes taxes & fees
Sep 1 - Sep 2
Captains Watch: A Coastal Escape
A room with a radiator, a potted plant, a striped ottoman, a wooden table, and a staircase leading to another room.

12. Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2

Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2
Brunswick
The price is ￥39,026
￥80,419 total
includes taxes & fees
Aug 25 - Aug 26
Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

13. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (6 reviews)
The price is ￥91,045
￥180,736 total
includes taxes & fees
Sep 1 - Sep 2
Three bedroom in United States of America, Freeport
A spacious living room with a wooden floor, a white sofa, a coffee table, and a dining area with a white table and chairs.

14. 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
9.0 out of 10, Wonderful, (6 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is ￥43,841
￥84,452 total
includes taxes & fees
Sep 1 - Sep 2
Beautiful 3BR Home with Office in Town of Brunswick with King beds
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

15. 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 ￥42,183
￥73,696 total
includes taxes & fees
Sep 16 - Sep 17
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A two-story house with a large porch, multiple windows, and a well-maintained lawn.

16. Maine Luxury Home On the Sea

Maine Luxury Home On the Sea
Brunswick
The price is ￥70,449
￥166,975 total
includes taxes & fees
Aug 27 - Aug 28
Maine Luxury Home On the Sea
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a granite countertop.

17. 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 ￥54,737
￥128,953 total
includes taxes & fees
Aug 20 - Aug 21
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
A cozy room with wooden flooring, wicker furniture, and a white brick wall.

18. 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, (4 reviews)
"Great location and super clean house"
United States
Gary R.
The price is ￥35,870
￥114,166 total
includes taxes & fees
Sep 16 - Sep 17
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
A living room with a grey sofa, a coffee table, and a dining area with a wooden table and chairs.

19. 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
8.8 out of 10, Excellent, (28 reviews)
"Perfect spot for us to spend a weekend up at Bowdoin where "
United States
Michaela M.
The price is ￥43,841
￥89,317 total
includes taxes & fees
Sep 1 - Sep 2
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

20. 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, (61 reviews)
"Nice place. Good location."
United States
Rob M.
The price is ￥21,783
￥66,882 total
includes taxes & fees
Sep 3 - Sep 4
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
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

8/10 Good
"This was a fine place to spend the night. Basic but clean room. Very thin walls. Decent breakfast. Very nice staff."
Laura 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
249
Accommodation
515 Vacation Homes
Lowest Price
￥26,587
Highest Price
￥301,140