
Search Vacation Homes in Bailey Island
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Bailey Island vacation homes

1. Orchid Harbor, Bailey Island 3BR
Orchid Harbor, Bailey Island 3BRHarpswell
10.0 out of 10, Exceptional, (13 reviews)
The price is ¥20,445
¥56,498 total
includes taxes & fees
Nov 10 - Nov 11

2. Mid Coast Getaway w/ water views
Mid Coast Getaway w/ water viewsWest Point
9.2 out of 10, Wonderful, (12 reviews)
The price is ¥16,578
¥32,321 total
includes taxes & fees
Nov 8 - Nov 9

3. Captains Watch: A Coastal Escape
Captains Watch: A Coastal EscapeWest Point
8.8 out of 10, Excellent, (3 reviews)
The price is ¥17,368
¥34,534 total
includes taxes & fees
Nov 5 - Nov 6

4. Full sized home
Full sized homeHarpswell
9.8 out of 10, Exceptional, (80 reviews)
The price is ¥31,578
¥54,900 total
includes taxes & fees
Nov 30 - Dec 1

5. 2 bedroom w/ expansive water views
2 bedroom w/ expansive water viewsWest Point
9.8 out of 10, Exceptional, (7 reviews)
The price is ¥20,723
¥37,183 total
includes taxes & fees
Nov 8 - Nov 9

6. Fantastic Waterfront Views
Fantastic Waterfront ViewsWest Point
9.4 out of 10, Exceptional, (23 reviews)
The price is ¥24,868
¥44,099 total
includes taxes & fees
Nov 8 - Nov 9

7. Mere Point Sunrise Views at Eastern Shore!
Mere Point Sunrise Views at Eastern Shore!Brunswick
9.8 out of 10, Exceptional, (10 reviews)
The price is ¥21,530
¥57,583 total
includes taxes & fees
Nov 16 - Nov 17

8. Classic New England Waterfront House Big Lawn Beautiful Sunrise
Classic New England Waterfront House Big Lawn Beautiful SunriseHarpswell
10.0 out of 10, Exceptional, (2 reviews)
The price is ¥55,262
¥252,299 total
includes taxes & fees
Dec 2 - Dec 3

9. Fully Updated Airy Historic Home in South Freeport
Fully Updated Airy Historic Home in South FreeportFreeport
10.0 out of 10, Exceptional, (1 review)
The price is ¥22,578
¥72,798 total
includes taxes & fees
Nov 6 - Nov 7

10. Quiet Spot in lovely Freeport neighborhood
Quiet Spot in lovely Freeport neighborhoodFreeport
The price is ¥22,373
¥60,281 total
includes taxes & fees
Nov 5 - Nov 6

11. Casco Bay Oceanfront Retreat by Everrow
Casco Bay Oceanfront Retreat by EverrowFreeport
10.0 out of 10, Exceptional, (13 reviews)
The price is ¥58,467
¥134,635 total
includes taxes & fees
Nov 8 - Nov 9

12. Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Private Home w/ Office Year Round in town Brunswick next to BowdoinBrunswick
8.8 out of 10, Excellent, (28 reviews)
The price is ¥26,052
¥62,989 total
includes taxes & fees
Dec 1 - Dec 2

13. The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & LuxuryHarpswell
10.0 out of 10, Exceptional, (2 reviews)
The price is ¥92,366
¥342,824 total
includes taxes & fees
Nov 8 - Nov 9

14. 1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!
1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!Bath
8.0 out of 10, Very good, (31 reviews)
The price is ¥17,621
¥26,607 total
includes taxes & fees
Nov 6 - Nov 7

15. Newly Renovated Luxury House with Game Room
Newly Renovated Luxury House with Game RoomYarmouth
10.0 out of 10, Exceptional, (4 reviews)
The price is ¥41,762
¥114,878 total
includes taxes & fees
Nov 9 - Nov 10

16. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.Bath
8.2 out of 10, Very good, (21 reviews)
The price is ¥18,068
¥26,950 total
includes taxes & fees
Nov 5 - Nov 6

17. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Brunswick 3BR Bungalow By Bowdoin With Fenced-In BackyardBrunswick
10.0 out of 10, Exceptional, (5 reviews)
The price is ¥38,683
¥111,177 total
includes taxes & fees
Nov 8 - Nov 9

18. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location
1200 sq ft ♦ West End Townhouse ♦ Perfect LocationWest End
8.6 out of 10, Excellent, (64 reviews)
The price is ¥16,640
¥57,205 total
includes taxes & fees
Nov 9 - Nov 10

19. Willard Square Family Home
Willard Square Family HomeWillard Beach
9.8 out of 10, Exceptional, (13 reviews)
The price is ¥56,525
¥101,451 total
includes taxes & fees
Nov 12 - Nov 13

20. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/ACGeorgetown
10.0 out of 10, Exceptional, (2 reviews)
The price is ¥33,252
¥59,665 total
includes taxes & fees
Nov 8 - Nov 9
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Bailey Island Hotel Reviews

Clarion Pointe South Portland
8/10 Good
Find out more about Bailey Island
Bailey Island Vacation Homes information
Number of reviews | 334 |
|---|---|
Accommodation | 613 Vacation Homes |
Lowest Price | ¥26,607 |
Highest Price | ¥342,824 |



































































