
Holiday Homes in Bailey Island
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Our top choices for Bailey Island holiday homes

1. Orchid Harbor, Bailey Island 3BR
Orchid Harbor, Bailey Island 3BRHarpswell
10.0 out of 10, Exceptional, (13 reviews)
The price is AU$584
includes taxes & fees
16 Nov - 17 Nov

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 AU$298
includes taxes & fees
22 Nov - 23 Nov

3. Full sized home
Full sized homeHarpswell
9.8 out of 10, Exceptional, (80 reviews)
The price is AU$494
includes taxes & fees
7 Dec - 8 Dec

4. 2 bedroom w/ expansive water views
2 bedroom w/ expansive water viewsWest Point
9.8 out of 10, Exceptional, (7 reviews)
The price is AU$343
includes taxes & fees
6 Dec - 7 Dec

5. 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 AU$500
includes taxes & fees
16 Nov - 17 Nov

6. Captains Watch: A Coastal Escape
Captains Watch: A Coastal EscapeWest Point
8.8 out of 10, Excellent, (3 reviews)
The price is AU$396
includes taxes & fees
15 Nov - 16 Nov

7. 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 AU$2,243
includes taxes & fees
7 Dec - 8 Dec

8. Fantastic Waterfront Views
Fantastic Waterfront ViewsWest Point
9.4 out of 10, Exceptional, (23 reviews)
The price is AU$398
includes taxes & fees
22 Nov - 23 Nov

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 AU$664
includes taxes & fees
11 Nov - 12 Nov

10. Quiet Spot in lovely Freeport neighborhood
Quiet Spot in lovely Freeport neighborhoodFreeport
The price is AU$488
includes taxes & fees
21 Nov - 22 Nov

11. Casco Bay Oceanfront Retreat by Everrow
Casco Bay Oceanfront Retreat by EverrowFreeport
10.0 out of 10, Exceptional, (13 reviews)
The price is AU$1,134
includes taxes & fees
12 Nov - 13 Nov

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 AU$570
includes taxes & fees
1 Dec - 2 Dec

13. 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 AU$257
includes taxes & fees
24 Nov - 25 Nov

14. 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 AU$3,060
includes taxes & fees
11 Nov - 12 Nov

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 AU$1,385
includes taxes & fees
16 Nov - 17 Nov

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 AU$277
includes taxes & fees
26 Nov - 27 Nov

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 AU$1,018
includes taxes & fees
11 Nov - 12 Nov

18. Charming Historic home steps away from downtown
Charming Historic home steps away from downtownBath
9.4 out of 10, Exceptional, (3 reviews)
The price is AU$917
includes taxes & fees
17 Nov - 18 Nov

19. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
1200 sq ft ♦ West End Townhouse ♦ Walk to Old PortWest End
8.6 out of 10, Excellent, (64 reviews)
The price is AU$498
includes taxes & fees
11 Nov - 12 Nov

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 AU$539
includes taxes & fees
11 Nov - 12 Nov
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

Clarion Pointe South Portland
10/10 Excellent
Find out more about Bailey Island
Bailey Island Holiday Homes information
Number of reviews | 324 |
|---|---|
Accommodation | 621 Holiday Homes |
Lowest Price | AU$257 |
Highest Price | AU$3,060 |



































































