Book Holiday Homes in Islesboro

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Featured Holiday Homes in Islesboro

Elegant Historic Home with Refined Interiors and Private Outdoor Spaces

Elegant Historic Home with Refined Interiors and Private Outdoor Spaces

Camden
A stay at this vacation home places you in the heart of Camden, steps from High Street Historic District and 4 minutes by foot from Camden Public Library.
Opens in a new windowElegant Historic Home with Refined Interiors and Private Outdoor Spaces
Charming Sandy Point Home

Charming Sandy Point Home

Stockton Springs
Located in Stockton Springs, this vacation home is a 2-minute drive from Penobscot River and 5 minutes from Penobscot Narrows Bridge and Observatory.
Opens in a new windowCharming Sandy Point Home
Cozy, heated 2-bedroom barn in peaceful Brooksville

Cozy, heated 2-bedroom barn in peaceful Brooksville

Brooksville
When you stay at this vacation home in Brooksville, you'll be by the sea and within a 5-minute drive of Great Island.
Opens in a new windowCozy, heated 2-bedroom barn in peaceful Brooksville
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New Colonial One Mile from Camden Harbor

New Colonial One Mile from Camden Harbor

2 out of 5
Camden
The price is AU$791 per night from 5 Nov to 6 Nov
AU$791
5 Nov - 6 Nov
includes taxes & fees
With a stay at this vacation home in Camden, you'll be within a 5-minute drive of Golfer's Crossing Mini Golf and Merryspring Park.
Opens in a new windowNew Colonial One Mile from Camden Harbor
Historic Home w/ Gas Fireplace, Fast WiFi, & Private W/D - Snowbird-Friendly

Historic Home w/ Gas Fireplace, Fast WiFi, & Private W/D - Snowbird-Friendly

Warren
Located in Warren, this vacation home is in a rural location, within a 5-minute drive of St. George River and Fawcett's Antique Toy and Art Museum.
Opens in a new windowHistoric Home w/ Gas Fireplace, Fast WiFi, & Private W/D - Snowbird-Friendly
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

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

Thomaston
The price is AU$576 per night from 8 Nov to 9 Nov
AU$576
8 Nov - 9 Nov
includes taxes & fees
With a stay at this vacation home in Thomaston, you'll be within a 5-minute drive of General Henry Knox Museum and Maine State Prison Store.
Opens in a new windowFire Pit & Grill, Movie Room, Workspace, A/C, Pets
The RiverView

The RiverView

Thomaston
The price is AU$425 per night from 5 Nov to 6 Nov
AU$425
5 Nov - 6 Nov
includes taxes & fees
Located in Thomaston, this vacation home is within a 5-minute drive of General Henry Knox Museum and Maine State Prison Store.
Opens in a new windowThe RiverView
Serene Luxury Coastal Retreat, Dock, Kayaks, Fishing, Wildlife, Exceptional View

Serene Luxury Coastal Retreat, Dock, Kayaks, Fishing, Wildlife, Exceptional View

Penobscot
With a stay at this vacation home in Penobscot, you'll be 8.1 mi (13.1 km) from Great Island and 8.9 mi (14.4 km) from Jonathan Fisher House.
Opens in a new windowSerene Luxury Coastal Retreat, Dock, Kayaks, Fishing, Wildlife, Exceptional View
Hillside House

Hillside House

Northport
With a stay at this vacation home in Lincolnville, you'll be within a 15-minute drive of Windsor Chairmakers and Lincolnville Beach.
Opens in a new windowHillside House
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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
449 Holiday Homes
Lowest Price
AU$210
Highest Price
AU$791
Popular accommodation
Elegant Historic Home with Refined Interiors and Private Outdoor Spaces, Charming Sandy Point Home, Cozy, heated 2-bedroom barn in peaceful Brooksville, New Colonial One Mile from Camden Harbor, Historic Home w/ Gas Fireplace, Fast WiFi, & Private W/D - Snowbird-Friendly, Fire Pit & Grill, Movie Room, Workspace, A/C, Pets, The RiverView, Serene Luxury Coastal Retreat, Dock, Kayaks, Fishing, Wildlife, Exceptional View, Hillside House

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.
Opens in a new windowIsland log home in Maine with ocean views
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$210 per night from 5 Nov to 6 Nov
AU$210
5 Nov - 6 Nov
includes taxes & fees
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.
Opens in a new windowFireside Inn & Suites - Belfast
Cedar Crest Inn

Cedar Crest Inn

2.5 out of 5
115 Elm Street, Camden, ME
When you stay at Cedar Crest Inn in Camden, you'll be near the beach, within a 10-minute walk of Merryspring Park and Golfer's Crossing Mini Golf.
Opens in a new windowCedar Crest Inn
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Colonial Gables Oceanfront Village

Colonial Gables Oceanfront Village

2.5 out of 5
7 Eagle Avenue, Belfast, ME
Fully refundableReserve now, pay when you stay
The price is AU$298 per night from 6 Nov to 7 Nov
AU$298
6 Nov - 7 Nov
includes taxes & fees
Located in Belfast, Colonial Gables Oceanfront Village is on the waterfront, a 4-minute walk from Perry's Nut House and within a 5-minute drive of Moose Point ...
Opens in a new windowColonial Gables Oceanfront Village
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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.