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Our top choices for Islesboro holiday rentals

1. Trade Winds on the Bay
Trade Winds on the BayRockland
8.6 out of 10, Excellent, (540 reviews)
The price is €101
includes taxes & fees
9 Nov - 10 Nov

2. Cozy Cabin By The Pond, Sleeps 2
Cozy Cabin By The Pond, Sleeps 2Waldo
10.0 out of 10, Exceptional, (236 reviews)
The price is €185
includes taxes & fees
9 Nov - 10 Nov

3. 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 €124
includes taxes & fees
9 Nov - 10 Nov

4. Restful Maine Cabin 6 • Fire Pit • Sauna • Beach
Restful Maine Cabin 6 • Fire Pit • Sauna • BeachStockton Springs
10.0 out of 10, Exceptional, (12 reviews)

5. 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 €339
includes taxes & fees
9 Nov - 10 Nov

6. NEW Dreamy cabin overlooking Penobscot Bay
NEW Dreamy cabin overlooking Penobscot BayStockton Springs
10.0 out of 10, Exceptional, (1 review)

7. Cozy Cabin 3 • Forest Escape • Cedar Sauna + Firepit
Cozy Cabin 3 • Forest Escape • Cedar Sauna + FirepitStockton Springs
10.0 out of 10, Exceptional, (9 reviews)

8. Cabin 1 Near Sandy Point Beach + Wood-Fired Sauna
Cabin 1 Near Sandy Point Beach + Wood-Fired SaunaStockton Springs
9.8 out of 10, Exceptional, (6 reviews)

9. Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna
Beautiful Maine Cabin 5 • Wood Fired Cedar SaunaStockton Springs
10.0 out of 10, Exceptional, (10 reviews)

10. Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna
Quiet Maine Cabin 2 • Hideaway in the Trees • SaunaStockton Springs
10.0 out of 10, Exceptional, (19 reviews)

11. Cabin 4 • Unwind in Nature • Beach • Cedar Sauna
Cabin 4 • Unwind in Nature • Beach • Cedar SaunaStockton Springs
10.0 out of 10, Exceptional, (5 reviews)

12. Fully Updated Airy Historic Home in West Rockport
Fully Updated Airy Historic Home in West RockportRockport
The price is €490
includes taxes & fees
9 Nov - 10 Nov

13. NEW BUILD Midcoast cabin! Sauna & walk to beach
NEW BUILD Midcoast cabin! Sauna & walk to beachStockton Springs

14. Lone Star Lodge - Newly Renovated Studio
Lone Star Lodge - Newly Renovated StudioNorthport
10.0 out of 10, Exceptional, (1 review)
The price is €331
includes taxes & fees
9 Nov - 10 Nov

15. Phoenix Nest - Downtown Apartment in Belfast
Phoenix Nest - Downtown Apartment in BelfastBelfast
9.4 out of 10, Exceptional, (3 reviews)
The price is €319
includes taxes & fees
9 Nov - 10 Nov

16. 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 €372
includes taxes & fees
9 Nov - 10 Nov

17. Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House
Cozy Little Carriage House with Spectacular Sunsets at The Rockbound HouseBrooklin
9.8 out of 10, Exceptional, (6 reviews)
The price is €262
includes taxes & fees
9 Nov - 10 Nov

18. Apt 1 Studio apartment in downtown Stonington
Apt 1 Studio apartment in downtown StoningtonStonington
9.8 out of 10, Exceptional, (87 reviews)
The price is €240
includes taxes & fees
13 Nov - 14 Nov

19. Brand new farm cottage close to downtown Blue Hill and Acadia National Park
Brand new farm cottage close to downtown Blue Hill and Acadia National ParkBlue Hill
9.4 out of 10, Exceptional, (42 reviews)
The price is €157
includes taxes & fees
9 Nov - 10 Nov

20. Blue Hill in the Woods
Blue Hill in the WoodsBlue Hill
9.2 out of 10, Wonderful, (5 reviews)
The price is €198
includes taxes & fees
13 Nov - 14 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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