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
Stay at this vacation home in Lincolnville. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Windsor Chairmakers and Lincolnville Beach ...
Stay in this beautiful home: ocean views and access to midcoast Maine's charm!
Charming Camden Home in a quiet and convenient location

Charming Camden Home in a quiet and convenient location

2 out of 5
Camden
Stay at this vacation home in Camden. Enjoy free WiFi, a garden, and patios. Popular attractions Mount Battie and Shirt Tail Point Park are located nearby.
Charming Camden Home in a quiet and convenient location
Oceanfront home on 6 acres with multi-level deck & spectacular view

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

Rockport
Book a stay at this beach vacation home in Rockport. Enjoy a beach locale, a garden, and patios. Popular attractions Beech Hill Preserve and Oakland Park Bowling ...
Oceanfront home on 6 acres with multi-level deck & spectacular view
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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 NZ$1,099 per night from 9 Feb to 10 Feb
NZ$1,099
includes taxes & fees
9 Feb - 10 Feb
Book a stay at this family-friendly vacation home in Camden. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Megunticook Lake and ...
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
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
Book a stay at this beach vacation home in Rockport. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Samoset Resort Golf Course and Chickawaukee ...
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 NZ$624 per night from 2 Feb to 3 Feb
NZ$624
includes taxes & fees
2 Feb - 3 Feb
Stay at this vacation home in Owls Head. Enjoy a garden, patios, and in-room washers/dryers. Popular attractions Breakwater Vineyards and Snow Marine Park are ...
Comfortable, Close to Town Home, with Oceanview.
Journeys End Loft

Journeys End Loft

Sedgwick
The price is NZ$520 per night from 1 Feb to 2 Feb
NZ$520
includes taxes & fees
1 Feb - 2 Feb
Stay at this vacation home in Sedgwick. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Friend Memorial Public Library and Deer ...
Journeys End Loft
Lovely Waterfront Owls Head Home w/ Own Beach

Lovely Waterfront Owls Head Home w/ Own Beach

Owls Head
Stay at this vacation home in Owls Head. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Owls Head State Park and Owls Head Lighthouse ...
Lovely Waterfront Owls Head Home w/ Own Beach
Gorgeous Oceanfront Retreat on Penobscot Bay

Gorgeous Oceanfront Retreat on Penobscot Bay

Lincolnville
The price is NZ$3,713 per night from 24 Jan to 25 Jan
NZ$3,713
includes taxes & fees
24 Jan - 25 Jan
Book a stay at this beach vacation home in Lincolnville. Enjoy a beach locale, a garden, and patios. Popular attractions Belfast City Park and Perry's Nut House ...
Gorgeous Oceanfront Retreat on Penobscot Bay
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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
361 Holiday Homes
Lowest Price
NZ$180
Highest Price
NZ$3,713
Popular accommodation
Stay in this beautiful home: ocean views and access to midcoast Maine's charm! , Charming Camden Home in a quiet and convenient location, Oceanfront home on 6 acres with multi-level deck & spectacular view, Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town, Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views , Comfortable, Close to Town Home, with Oceanview., Journeys End Loft, Lovely Waterfront Owls Head Home w/ Own Beach, Gorgeous Oceanfront Retreat on Penobscot Bay

Top trending hotels in Islesboro

Island log home in Maine with ocean views

Island log home in Maine with ocean views

Islesboro
Stay at this vacation home in Islesboro. Enjoy free WiFi, a garden, and patios. Popular attractions Warren Island State Park and Windsor Chairmakers are located ...
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 NZ$229 per night from 26 Jan to 27 Jan
NZ$229
includes taxes & fees
26 Jan - 27 Jan
Book a stay at this business-friendly hotel in Rockport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
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 NZ$180 per night from 27 Jan to 28 Jan
NZ$180
includes taxes & fees
27 Jan - 28 Jan
Stay at this 3.5-star aparthotel in Rockland. Enjoy free WiFi, free parking, and a health club. Our guests praise the helpful staff and the clean rooms in our ...
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 NZ$254 per night from 16 Feb to 17 Feb
NZ$254
includes taxes & fees
16 Feb - 17 Feb
Book a stay at this business-friendly hotel in Thomaston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.