Book Holiday Homes in Islesboro

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

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.
Elegant Historic Home with Refined Interiors and Private Outdoor Spaces
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
1812 Pierce House

1812 Pierce House

3.5 out of 5
384 S Main St, Winterport, ME
With a stay at 1812 Pierce House in Winterport, you'll be within a 5-minute walk of Winterport Winery and Penobscot River.
1812 Pierce House
Save an average of 15% on thousands of hotels when you're signed in
Charming Antique Cape, Water View, Historic Castine, Penobscot Bay.

Charming Antique Cape, Water View, Historic Castine, Penobscot Bay.

Castine
When you stay at this vacation home in Castine, you'll be next to a golf course, within a 5-minute drive of Main Street and Castline Golf Club.
Charming Antique Cape, Water View, Historic Castine, Penobscot Bay.
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.
Charming Sandy Point Home
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

2 out of 5
South Thomaston
Located in South Thomaston, this vacation home is by the ocean, within a 10-minute drive of General Henry Knox Museum and Maine State Prison Store.
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill

Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill

Winterport
With a stay at this vacation home in Winterport, you'll be on the waterfront, just steps from Penobscot River and a 3-minute drive from Winterport Winery.
Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill
Brand New! Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

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

Thomaston
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.
Brand New! Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach

Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach

Lincolnville
The price is AU$453 per night from 2 Sept to 3 Sept
AU$453
2 Sept - 3 Sept
includes taxes & fees
Located in Lincolnville, this vacation home is by the sea, within a 5-minute walk of Lincolnville Beach and Lincolnville Ferry Terminal.
Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach
Don't see what you're looking for?
See all available properties in Islesboro
View all properties
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
547 Holiday Homes
Lowest Price
AU$235
Highest Price
AU$453
Popular accommodation
Elegant Historic Home with Refined Interiors and Private Outdoor Spaces, Island log home in Maine with ocean views, 1812 Pierce House, Charming Antique Cape, Water View, Historic Castine, Penobscot Bay., Charming Sandy Point Home, Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm, Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill, Brand New! Fire Pit & Grill, Movie Room, Workspace, A/C, Pets, Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to 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
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$359 per night from 2 Sept to 3 Sept
AU$359
2 Sept - 3 Sept
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.
Fireside Inn & Suites - Belfast
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$335 per night from 2 Sept to 3 Sept
AU$335
2 Sept - 3 Sept
includes taxes & fees
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
Save an average of 15% on thousands of hotels when you're signed in
Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is AU$235 per night from 5 Aug to 6 Aug
AU$235
5 Aug - 6 Aug
includes taxes & fees
A stay at Harborline Hotel places you in the heart of Rockland, steps from Maine Lighthouse Museum and Buoy Park.
Harborline Hotel
Don't see what you're looking for?
See all available properties in Islesboro
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.