Photo by Colleen Johnson

Islesboro Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Islesboro

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very Good, (246)
"Location is amazing."
Trade Winds on the Bay

Point Lookout

3.0 star property
9.2 out of 10, Wonderful, (5)
"Great location. Away from the down town bustle, but close enough to enjoy the best of both worlds. Clean cabin, great amenities. "
Point Lookout

Cozy 2 BR by River- Crooked Steeple Hall

4.0 star property
Cozy 2 BR by River- Crooked Steeple Hall

1812 Pierce House

3.5 star property
1812 Pierce House

35 Mi to Acadia: Rustic Retreat in Orland!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Exactly what you think of a cabin in the Maine woods. Close to Bucksport. No wifi. Only got one channel on the rabbit ears for the TV, but many movies available to use on the dvd player. Dark outside at night. Quick response from property manager. Would stay there again. "
35 Mi to Acadia: Rustic Retreat in Orland!

Pet-friendly Prospect Apartment: 7 Mi to Beach!

3.0 star property
7.0 out of 10, Good, (2)
"Like: Very private, close to nature, extra blankets available, very clean kitchen and bathroom, towels and cafe k-cups available Didn't like: Mattress, odor in the bathroom, yellow pillow under pillowcase"
Pet-friendly Prospect Apartment: 7 Mi to Beach!

Pine Grove Cottages

2.5 star property
9.8 out of 10, Exceptional, (88)
"Wonderful quiet place, The Host was a great person."
The price is P13,056
P14,942 total
includes taxes & fees
Aug 14 - Aug 15
Pine Grove Cottages
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Islesboro Hotel Reviews

Frequently asked questions

Can I find a vacation rental in Islesboro?

Yes, you can find vacation rentals close to the most popular points of interest in Islesboro, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Islesboro has to offer?

1812 Pierce House: This vacation home rental outside Islesboro is equipped with a barbecue grill, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Islesboro?

With 9 Expedia vacation rentals, you're sure 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 Perry's Nut House, 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 larger area.

What’s a vacation rental in Islesboro like?

Vacation rentals are private properties where you can stay for short or long periods in Islesboro. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips.