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!
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
Charming Camden Home in a quiet and convenient location

Charming Camden Home in a quiet and convenient location

2 out of 5
Camden
With a stay at this vacation home in Camden, you'll be within a 15-minute walk of Camden Hills State Park and Shirt Tail Point Park.
Charming Camden Home in a quiet and convenient location
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Perfect location  ! Harbor Breeze is on Camden Harbor & walking distance to town

Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town

Camden
The price is AU$1,002 per night from 8 Feb to 9 Feb
AU$1,002
includes taxes & fees
8 Feb - 9 Feb
A stay at this vacation home places you in the heart of Camden, within a 10-minute walk of Camden Harbor Park and Amphitheatre and Camden Public Library.
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Gorgeous Oceanfront Retreat on Penobscot Bay

Gorgeous Oceanfront Retreat on Penobscot Bay

Lincolnville
The price is AU$3,449 per night from 9 Mar to 10 Mar
AU$3,449
includes taxes & fees
9 Mar - 10 Mar
Located in Lincolnville, this vacation home is by the ocean, within a 10-minute drive of Waldo County General Hospital and Belfast City Park.
Gorgeous Oceanfront Retreat on Penobscot Bay
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views

Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views

Rockport
When you stay at this vacation home in Rockport, you'll be on the beach, within a 5-minute drive of Oakland Park Bowling Lanes and Owls Head Lighthouse.
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Owls Head
The price is AU$562 per night from 7 Feb to 8 Feb
AU$562
includes taxes & fees
7 Feb - 8 Feb
When you stay at this vacation home in Owls Head, you'll be by the sea, within a 5-minute drive of Breakwater Vineyards and Coastal Children's Museum.
Comfortable, Close to Town Home, with Oceanview.
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
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
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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
360 Holiday Homes
Lowest Price
AU$162
Highest Price
AU$3,449
Popular accommodation
Stay in this beautiful home: ocean views and access to midcoast Maine's charm! , Oceanfront home on 6 acres with multi-level deck & spectacular view, Charming Camden Home in a quiet and convenient location, Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town, Gorgeous Oceanfront Retreat on Penobscot Bay , Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views , Comfortable, Close to Town Home, with Oceanview., Lovely Waterfront Owls Head Home w/ Own Beach, Relaxing lodge in the woods

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$206 per night from 17 Feb to 18 Feb
AU$206
includes taxes & fees
17 Feb - 18 Feb
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
Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
2 Park Dr, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 17 Feb to 18 Feb
AU$162
includes taxes & fees
17 Feb - 18 Feb
A stay at Trade Winds on the Bay places you in the heart of Rockland, steps from Maine Lighthouse Museum and Project Puffin Visitor Center.
Trade Winds on the Bay
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Hampton Inn & Suites Rockland

Hampton Inn & Suites Rockland

2.5 out of 5
190 New County Rd, Thomaston, ME
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 18 Feb to 19 Feb
AU$209
includes taxes & fees
18 Feb - 19 Feb
When you stay at Hampton Inn & Suites Rockland in Thomaston, you'll be near the airport, within a 5-minute drive of Rockland Harbor Park and Maine Lighthouse ...
Hampton Inn & Suites Rockland
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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.