Photo by Colleen Johnson

Islesboro Holiday Rentals

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Check prices for these dates

Tonight
9 Jan - 10 Jan
Tomorrow
10 Jan - 11 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

Our top choices for Islesboro holiday rentals

Lobby sitting area
Trade Winds on the Bay

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.4 out of 10, Very good, (328)
"great value, nice large room, clean and everything needed. No continental breakfast offered but still good value"
United States
Mark
Trade Winds on the Bay
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 Islesboro Hotel Reviews

Trade Winds on the Bay

Trade Winds on the Bay

10/10 Excellent
"The room was great. Warm and spacious. Price was fabulous and staff was very warm and accommodating It is a short walk to Main Street Rockland. Coffe bar was very good. It was a winter visit so it was quiet. We were the only ones at pool and sauna"
Margaret 1-night trip
Posted 2 days ago
Trade Winds on the Bay

Frequently asked questions

Can I find a holiday rental in Islesboro?

Yes, there are holiday rentals close to the most popular sights in Islesboro, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Islesboro?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Islesboro stay.

What’s there to see and do in Islesboro?

While exploring the area, visit family-friendly sights like Coastal Children's Museum, or get outside and enjoy nature at Lincolnville Beach. Warren Island State Park and Camden Hills State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Islesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islesboro. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for families.