Photo by Colleen Johnson

Search Holiday Rentals in Islesboro

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Holiday Rentals in Islesboro

Trade Winds on the Bay
Water view

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very good, (245)
"Location is amazing."
Trade Winds on the Bay
Point Lookout
Exterior

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
1812 Pierce House
Front of property

1812 Pierce House

3.5 star property
1812 Pierce House
Cozy 2 BR by River- Crooked Steeple Hall
Signature House, 2 Bedrooms, Patio, River View | Private kitchen | Fridge, microwave, oven, stovetop

Cozy 2 BR by River- Crooked Steeple Hall

4.0 star property
The price is 9.181.550 ₫
10.007.889 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Cozy 2 BR by River- Crooked Steeple Hall
35 Mi to Acadia: Rustic Retreat in Orland!
House (1 Bedroom) | Interior

35 Mi to Acadia: Rustic Retreat in Orland!

2.0 star property
35 Mi to Acadia: Rustic Retreat in Orland!
Pet-friendly Prospect Apartment: 7 Mi to Beach!
Interior

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
Exterior

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 6.004.109 ₫
6.871.734 ₫ total
includes taxes & fees
10 Aug - 11 Aug
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
Sign in
Sign up, it's free

Top Islesboro Hotel Reviews

Lord Camden Inn

Lord Camden Inn

10/10 Excellent
"So close to shopping, restaurants and the harbor. "
Regina 3-night trip
Posted 23 hours ago
Lord Camden Inn

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 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 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.