Name: Trade Winds on the Bay
Rating: 8.6

Photo by Colleen Johnson

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Your Islesboro Holiday

Prepare to experience Islesboro in your own style with a custom Islesboro holiday package! Uncovering the charms of this city is made easier with a base in a neighbourhood such as Bayside, which is good for history, among many other things. Fill your itinerary with tours of Windsor Chairmakers, Warren Island State Park and Schoolhouse Museum, some of the things you shouldn't miss during your trip to Islesboro. Stop dreaming and start adventuring. Browse the many options on Expedia today and put your Islesboro holiday plans into gear!

Islesboro Holiday

Islesboro Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Knox County Regional Airport (RKD)
Population	630
Max Temp Winter	-1.11ºC
Max Temp Summer	24ºC
Top Sights	Moose Point State Park, Cellardoor Winery and Belfast Historical Society and Museum

Our pick of the best Islesboro Hotel Deals

Island log home in Maine with ocean views

Islesboro ME

10/10 Exceptional! (88 reviews)

Everything was perfect! The downside was that the stay was cut short as our work finished early1

Reviewed on 12 Dec 2025

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Fireside Inn & Suites - Belfast

159 Searsport Avenue Belfast ME

Fully refundableReserve now, pay when you stay

AU$189

15 Mar - 16 Mar

includes taxes & fees

9/10 Wonderful! (1,007 reviews)

I book a room based on a heated indoor pool. And though this establishment did in fact have a beautiful indoor pool. The pool itself was not heated. The room surrounding the pool was heated but not the pool water itself. Actually it was pretty chilly. The room was clean enough but the bed was very ...

Reviewed on 9 Mar 2026

Trade Winds on the Bay

2 Park Dr Rockland ME

Fully refundableReserve now, pay when you stay

8.6/10 Excellent! (355 reviews)

Trade Winds has undergone an impressive facelift. The room had been tastefully renovated, furnishings updated and upgraded, the room was clean and comfortable. The king bed was comfy with high quality bedding, the suite included a separate sitting space with pullout couch, table/chairs, coffee bar, ...

Reviewed on 9 Mar 2026

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See all 1,357 properties in Islesboro

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.