- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Our top choices for Bailey Island holiday rentals

1. Sunset Hideaway on Bailey Island
Sunset Hideaway on Bailey IslandHarpswell
9.0 out of 10, Wonderful, (8 reviews)
The price is NZ$336
includes taxes & fees
16 Nov - 17 Nov

2. Orchid Harbor, Bailey Island 3BR
Orchid Harbor, Bailey Island 3BRHarpswell
10.0 out of 10, Exceptional, (13 reviews)
The price is NZ$719
includes taxes & fees
16 Nov - 17 Nov

3. Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Bird Watching Paradise @ Waterfront Harpswell with Private DeckHarpswell
10.0 out of 10, Exceptional, (3 reviews)
The price is NZ$580
includes taxes & fees
15 Nov - 16 Nov

4. Mid Coast Getaway w/ water views
Mid Coast Getaway w/ water viewsWest Point
9.2 out of 10, Wonderful, (12 reviews)
The price is NZ$366
includes taxes & fees
16 Nov - 17 Nov

5. Studio Apartment in Freeport
Studio Apartment in FreeportFreeport
10.0 out of 10, Exceptional, (4 reviews)
The price is NZ$254
includes taxes & fees
16 Nov - 17 Nov

6. 2 bedroom w/ expansive water views
2 bedroom w/ expansive water viewsWest Point
9.8 out of 10, Exceptional, (7 reviews)
The price is NZ$421
includes taxes & fees
18 Nov - 19 Nov

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 NZ$619
includes taxes & fees
18 Nov - 19 Nov

8. Full sized home
Full sized homeHarpswell
9.8 out of 10, Exceptional, (80 reviews)
The price is NZ$602
includes taxes & fees
30 Nov - 1 Dec

9. Quiet Spot in lovely Freeport neighborhood
Quiet Spot in lovely Freeport neighborhoodFreeport
The price is NZ$605
includes taxes & fees
14 Nov - 15 Nov

10. Captains Watch: A Coastal Escape
Captains Watch: A Coastal EscapeWest Point
8.8 out of 10, Excellent, (3 reviews)
The price is NZ$494
includes taxes & fees
19 Nov - 20 Nov

11. 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 NZ$818
includes taxes & fees
14 Nov - 15 Nov

12. Fantastic Waterfront Views
Fantastic Waterfront ViewsWest Point
9.4 out of 10, Exceptional, (24 reviews)
The price is NZ$500
includes taxes & fees
16 Nov - 17 Nov

13. 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 NZ$2,779
includes taxes & fees
8 Dec - 9 Dec

14. Large suite/private bath/private entrance on quiet street near Thomas Bay
Large suite/private bath/private entrance on quiet street near Thomas BayBrunswick
10.0 out of 10, Exceptional, (176 reviews)
The price is NZ$210
includes taxes & fees
22 Nov - 23 Nov

15. Great suburban location close to town!
Great suburban location close to town!Deering Center
9.4 out of 10, Exceptional, (6 reviews)
The price is NZ$140
includes taxes & fees
19 Nov - 20 Nov

16. Cabin w/ bath + kitchenette | Hot tub add-on - 03
Cabin w/ bath + kitchenette | Hot tub add-on - 03Freeport
9.8 out of 10, Exceptional, (10 reviews)
The price is NZ$599
includes taxes & fees
18 Nov - 19 Nov

17. King Size Sun Rise Midcoast Lovely Stay
King Size Sun Rise Midcoast Lovely StayTopsham
9.6 out of 10, Exceptional, (19 reviews)
The price is NZ$381
includes taxes & fees
15 Nov - 16 Nov

18. 1st FL Downtown Grand Brunswick
1st FL Downtown Grand BrunswickBrunswick
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$478
includes taxes & fees
8 Dec - 9 Dec

19. Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown FreeportFreeport
10.0 out of 10, Exceptional, (12 reviews)

20. King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
King size Bed Big Smile Big Sunshine 1st FL Washer&DryerTopsham
9.6 out of 10, Exceptional, (8 reviews)
The price is NZ$430
includes taxes & fees
16 Nov - 17 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.
Find holiday rentals that suit your style

Apartments

Aparthotels















































































