Book Holiday Homes in Islesboro
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Featured Holiday Homes in Islesboro

Elegant Historic Home with Refined Interiors and Private Outdoor Spaces

Island log home in Maine with ocean views

1812 Pierce House

Charming Antique Cape, Water View, Historic Castine, Penobscot Bay.

Charming Sandy Point Home

Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill

Brand New! Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach
Islesboro Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Islesboro vacation homes are the perfect way for you to wing it.
Holiday houses in Islesboro let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Islesboro in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Islesboro adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Islesboro with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Islesboro vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Islesboro Holiday Homes essential information
Accommodation | 547 Holiday Homes |
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Lowest Price | NZ$257 |
Highest Price | NZ$491 |
Popular accommodation | Elegant Historic Home with Refined Interiors and Private Outdoor Spaces, Island log home in Maine with ocean views, 1812 Pierce House, Charming Antique Cape, Water View, Historic Castine, Penobscot Bay., Charming Sandy Point Home, Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm, Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill, Brand New! Fire Pit & Grill, Movie Room, Workspace, A/C, Pets, Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach |
More accommodations in Islesboro
Top trending hotels in Islesboro

Island log home in Maine with ocean views

Fireside Inn & Suites - Belfast

The Country Inn at Camden Rockport

Harborline Hotel
More ways to explore Islesboro
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^Subject to availability and chosen travel dates.