Book Holiday Homes in Islesboro

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Featured Holiday Homes in Islesboro

Stay in this beautiful home: ocean views and access to midcoast Maine's charm!

Stay in this beautiful home: ocean views and access to midcoast Maine's charm!

Lincolnville
With a stay at this vacation home in Lincolnville, you'll be a 1-minute walk from Windsor Chairmakers and 8 minutes by foot from Lincolnville Beach.
Stay in this beautiful home: ocean views and access to midcoast Maine's charm!
2 Bedroom Close to Town Home

2 Bedroom Close to Town Home

Thomaston
The price is AU$415 per night from 1 Jun to 2 Jun
AU$415
includes taxes & fees
1 June - 2 June
Located in Thomaston, this vacation home is within a 5-minute drive of General Henry Knox Museum and Maine State Prison Store.
2 Bedroom Close to Town Home
Oceanfront home on 6 acres with multi-level deck & spectacular view

Oceanfront home on 6 acres with multi-level deck & spectacular view

Rockport
Located in Rockport, this vacation home is by the ocean, within a 5-minute drive of Beech Hill Preserve and Oakland Park Bowling Lanes.
Oceanfront home on 6 acres with multi-level deck & spectacular view
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Oceanfront retreat with sunrise views, screened porch, & deck

Oceanfront retreat with sunrise views, screened porch, & deck

Brooklin
Located in Brooklin, this vacation home is by the ocean, within a 15-minute drive of Friend Memorial Public Library and Blue Hill Books.
Oceanfront retreat with sunrise views, screened porch, & deck
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Rockport
Located in Rockport, this vacation home is by the ocean, within a 5-minute drive of Oakland Park Bowling Lanes and Owls Head Lighthouse.
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
Secluded lakefront home with patio & firepit, fast WiFi, wood stove & W/D

Secluded lakefront home with patio & firepit, fast WiFi, wood stove & W/D

Ellsworth
Located in Ellsworth, this vacation home is on the waterfront, within a 15-minute drive of Toddy Pond and Rooster Brother Coffee Roasters.
Secluded lakefront home with patio & firepit, fast WiFi, wood stove & W/D
Relaxing lodge in the woods

Relaxing lodge in the woods

Frankfort
Located in Frankfort, this vacation home is in a rural location, within a 10-minute drive of Winterport Winery and Penobscot River.
Relaxing lodge in the woods
In-town, coastal + relaxing in Rockland

In-town, coastal + relaxing in Rockland

Rockland
The price is AU$805 per night from 5 May to 6 May
AU$805
includes taxes & fees
5 May - 6 May
A stay at this vacation home places you in the heart of Rockland, within a 5-minute walk of Sandy Beach and Coastal Children's Museum.
In-town, coastal + relaxing in Rockland
Lovely Waterfront Owls Head Home w/ Own Beach

Lovely Waterfront Owls Head Home w/ Own Beach

Owls Head
Located in Owls Head, this vacation home is on the waterfront, within a 5-minute drive of Owls Head State Park and Crescent Beach.
Lovely Waterfront Owls Head Home w/ Own Beach
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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.

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
443 Holiday Homes
Lowest Price
AU$219
Highest Price
AU$805
Popular accommodation
Stay in this beautiful home: ocean views and access to midcoast Maine's charm! , 2 Bedroom Close to Town Home, Oceanfront home on 6 acres with multi-level deck & spectacular view, Oceanfront retreat with sunrise views, screened porch, & deck, Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach, Secluded lakefront home with patio & firepit, fast WiFi, wood stove & W/D, Relaxing lodge in the woods, In-town, coastal + relaxing in Rockland, Lovely Waterfront Owls Head Home w/ Own Beach

Top trending hotels in Islesboro

Island log home in Maine with ocean views

Island log home in Maine with ocean views

Islesboro
When you stay at this vacation home in Islesboro, you'll be 6 minutes by car from Warren Island State Park.
Island log home in Maine with ocean views
The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
8 Country Inn Way, Rockport, ME
Fully refundableReserve now, pay when you stay
The price is AU$219 per night from 13 May to 14 May
AU$219
includes taxes & fees
13 May - 14 May
When you stay at The Country Inn at Camden Rockport in Rockport, you'll be near the beach, just steps from Golfer's Crossing Mini Golf and 9 minutes by foot ...
The Country Inn at Camden Rockport
Camden Riverhouse Hotel

Camden Riverhouse Hotel

2.5 out of 5
11 Tannery Lane, Camden, ME
The price is AU$236 per night from 3 May to 4 May
AU$236
includes taxes & fees
3 May - 4 May
With a stay at Camden Riverhouse Hotel, you'll be centrally located in Camden, steps from Camden Public Library and within a 5-minute walk of Camden Opera ...
Camden Riverhouse Hotel
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Fireside Inn & Suites - Belfast

Fireside Inn & Suites - Belfast

3 out of 5
159 Searsport Avenue, Belfast, ME
Fully refundableReserve now, pay when you stay
The price is AU$246 per night from 12 May to 13 May
AU$246
includes taxes & fees
12 May - 13 May
Located in Belfast, Fireside Inn & Suites - Belfast is on the waterfront, a 5-minute drive from Penobscot Marine Museum and 6 minutes from Belfast Harbor.
Fireside Inn & Suites - Belfast
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See all available properties in Islesboro
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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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^Subject to availability and chosen travel dates.