Photo by Colleen Johnson

Islesboro Holiday Rentals

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Holiday Rentals in Islesboro

Trade Winds on the Bay
3.5 star property
8.0 out of 10, Very good, (137)
"Everything was wonderful. We will stay there again"
The price is S$150
includes taxes & fees
23 Nov - 24 Nov
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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Other types of properties in Islesboro you may be interested in

Fireside Inn & Suites - Belfast
3.0 star property
8.8 out of 10, Excellent, (755)
"Very clean, great pet amenities."
The price is S$175
includes taxes & fees
9 Dec - 10 Dec
Fireside Inn & Suites - Belfast
The Country Inn at Camden Rockport
2.5 star property
9.6 out of 10, Exceptional, (1004)
"My family and I stayed as we got my dad’s house ready for him to move and sell it. It was a great way to relax after a long day of hard work. We enjoyed the pool and hot tub very much in the evening. "
The price is S$174
includes taxes & fees
26 Nov - 27 Nov
The Country Inn at Camden Rockport
Belfast Harbor Inn
3.5 star property
9.6 out of 10, Exceptional, (1003)
"Incredibly clean…..breakfast was really good. Friendly server."
The price is S$216
includes taxes & fees
5 Dec - 6 Dec
Belfast Harbor Inn
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 10 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 ALLPLaY Family Entertainment Center, or get outside and enjoy nature at Warren Island State Park. Lincolnville Beach and Pitcher Pond 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.