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Our top choices for Islesboro holiday homes

1. Simplicity-Just what you need! STR24-20
Simplicity-Just what you need! STR24-20Rockland
9.8 out of 10, Exceptional, (41 reviews)
The price is NZ$244
includes taxes & fees
14 Nov - 15 Nov

2. Waterfront Getaway Near Acadia w/ Spectacular View
Waterfront Getaway Near Acadia w/ Spectacular ViewDeer Isle
9.8 out of 10, Exceptional, (27 reviews)
The price is NZ$673
includes taxes & fees
10 Nov - 11 Nov

3. Fully Updated Airy Historic Home in West Rockport
Fully Updated Airy Historic Home in West RockportRockport
The price is NZ$989
includes taxes & fees
10 Nov - 11 Nov

4. Harbor/🦞 Pound Access & Views from Large Deck
Harbor/🦞 Pound Access & Views from Large DeckOwls Head
9.6 out of 10, Exceptional, (84 reviews)
The price is NZ$714
includes taxes & fees
10 Nov - 11 Nov

5. Tides' Reach - Private Waterfront King Beds
Tides' Reach - Private Waterfront King BedsOrland
9.8 out of 10, Exceptional, (29 reviews)
The price is NZ$742
includes taxes & fees
10 Nov - 11 Nov

6. 2 Bedroom Close to Town Home
2 Bedroom Close to Town HomeThomaston
8.8 out of 10, Excellent, (59 reviews)
The price is NZ$437
includes taxes & fees
18 Nov - 19 Nov

7. Comfortable, Close to Town Home, with Oceanview.
Comfortable, Close to Town Home, with Oceanview.Owls Head
9.6 out of 10, Exceptional, (104 reviews)
The price is NZ$578
includes taxes & fees
22 Nov - 23 Nov

8. Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Cheerful Two Bedroom Cabin - 10 minutes to Camden!Lincolnville
9.8 out of 10, Exceptional, (16 reviews)
The price is NZ$969
includes taxes & fees
10 Nov - 11 Nov

9. Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Relaxing Two Bedroom Cabin - 10 minutes to Camden!Lincolnville
8.4 out of 10, Very good, (6 reviews)
The price is NZ$969
includes taxes & fees
10 Nov - 11 Nov

10. Inkwell Suite at Spofford Lodge
Inkwell Suite at Spofford LodgeBucksport
10.0 out of 10, Exceptional, (22 reviews)
The price is NZ$382
includes taxes & fees
7 Dec - 8 Dec

11. Bright 2-Bedroom Apartment Near Downtown Thomaston
Bright 2-Bedroom Apartment Near Downtown ThomastonThomaston
9.2 out of 10, Wonderful, (17 reviews)
The price is NZ$399
includes taxes & fees
1 Dec - 2 Dec

12. Peaceful, Centrally Located Home with Seasonal River Views
Peaceful, Centrally Located Home with Seasonal River ViewsThomaston
9.6 out of 10, Exceptional, (41 reviews)
The price is NZ$448
includes taxes & fees
1 Dec - 2 Dec

13. Meadow Place Modern 3BR Belfast Getaway with Deck
Meadow Place Modern 3BR Belfast Getaway with DeckBelfast
The price is NZ$1,127
includes taxes & fees
10 Nov - 11 Nov

14. Spacious, bright, oceanfront house on the Blue Hill Peninsula.
Spacious, bright, oceanfront house on the Blue Hill Peninsula.Penobscot
10.0 out of 10, Exceptional, (8 reviews)
The price is NZ$1,365
includes taxes & fees
7 Dec - 8 Dec

15. Silver Oak Retreat Private Forest Getaway
Silver Oak Retreat Private Forest GetawayBelfast
The price is NZ$1,040
includes taxes & fees
19 Nov - 20 Nov

16. In-town, coastal + relaxing in Rockland
In-town, coastal + relaxing in RocklandRockland
10.0 out of 10, Exceptional, (58 reviews)
The price is NZ$967
includes taxes & fees
13 Nov - 14 Nov

17. A+ on Harbor w/ 8 Kayaks, Deck, Patio, Beach, Walk To Town, Best Views
A+ on Harbor w/ 8 Kayaks, Deck, Patio, Beach, Walk To Town, Best ViewsStonington
9.8 out of 10, Exceptional, (54 reviews)

18. Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to townCamden
9.2 out of 10, Wonderful, (90 reviews)
The price is NZ$1,951
includes taxes & fees
12 Nov - 13 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.
Learn more about Islesboro
This tranquil island offers scenic bike rides along coastal roads and peaceful beaches perfect for swimming at Pendleton Point. Catch the ferry to explore historic lighthouses or rent kayaks to paddle around the island's protected harbours.

Photo by Colleen Johnson
Open Photo by Colleen Johnson






















































































