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!
Journeys End Loft

Journeys End Loft

Sedgwick
The price is AU$501 per night from 17 Jan to 18 Jan
AU$501
includes taxes & fees
17 Jan - 18 Jan
Located in Sedgwick, this vacation home is within a 15-minute drive of Deer Isle Bridge and Friend Memorial Public Library.
Journeys End Loft
2 Bedroom Close to Town Home

2 Bedroom Close to Town Home

Thomaston
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
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Gorgeous new mid-coast listing! Large, family friendly home, perfect location!

Gorgeous new mid-coast listing! Large, family friendly home, perfect location!

Rockport
Located in Rockport, this vacation home is within a 5-minute drive of Chickawaukee Lake and Chickawaukie Pond.
Gorgeous new mid-coast listing! Large, family friendly home, perfect location!
The RiverView

The RiverView

Thomaston
Located in Thomaston, this vacation home is within a 5-minute drive of General Henry Knox Museum and Maine State Prison Store.
The RiverView
Breathtaking views, total relaxation, do as much or as little as you choose

Breathtaking views, total relaxation, do as much or as little as you choose

Owls Head
Located in Owls Head, this vacation home is by the ocean, within a 10-minute drive of Lucia Beach and Breakwater Vineyards.
Breathtaking views, total relaxation, do as much or as little as you choose
Ground-floor duplex with WiFi & W/D - walk to river and downtown

Ground-floor duplex with WiFi & W/D - walk to river and downtown

Bucksport
When you a stay at this vacation home in Bucksport, you'll be by the sea, within a 5-minute walk of Northeast Historic Film and Buck Cemetery.
Ground-floor duplex with WiFi & W/D - walk to river and downtown
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine

Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine

Searsmont
When you stay at this vacation home in Searsmont, you'll be in the mountains and 7 minutes by car from St. George River.
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine
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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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
AU$209
Highest Price
AU$501
Popular accommodation
Stay in this beautiful home: ocean views and access to midcoast Maine's charm! , Journeys End Loft, 2 Bedroom Close to Town Home, Gorgeous new mid-coast listing! Large, family friendly home, perfect location!, The RiverView, Breathtaking views, total relaxation, do as much or as little as you choose, Ground-floor duplex with WiFi & W/D - walk to river and downtown, Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine, Charming Camden Home in a quiet and convenient location

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$209 per night from 7 Jan to 8 Jan
AU$209
includes taxes & fees
7 Jan - 8 Jan
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$211 per night from 17 Jan to 18 Jan
AU$211
includes taxes & fees
17 Jan - 18 Jan
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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Rockland Harbor Hotel

Rockland Harbor Hotel

2.5 out of 5
520 Main Street, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is AU$284 per night from 26 Jan to 27 Jan
AU$284
includes taxes & fees
26 Jan - 27 Jan
A stay at Rockland Harbor Hotel places you in the heart of Rockland, steps from Rockland Ferry Terminal and 3 minutes by foot from Strand Theater.
Rockland Harbor Hotel
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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.