Islesboro Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Islesboro vacation rentals

Lobby sitting area

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (338 reviews)
"Very nice place "
United States
Robert
$99 nightly
The price is $108
Feb 23 - Feb 24
Total with taxes and fees
Trade Winds on the Bay
Interior

Bayside vista

Bayside vista
Bucksport
10.0 out of 10, Exceptional, (16 reviews)
"Very spacious space with all if the amenities a group or family could need. The view is spectacular, the kitchen is nice, and I especially loved lounging on the giant couch!"
United States
Jason R.
$301 nightly
The price is $328
Feb 6 - Feb 7
Total with taxes and fees
Bayside vista
Fridge, microwave, oven, stovetop

Tides' Reach - Private Waterfront King Beds

Tides' Reach - Private Waterfront King Beds
Orland
9.8 out of 10, Exceptional, (24 reviews)
"Communication with the host was great. They responded quickly and give us all the information we needed. Appreciated the seclusion of the property, but still near important resources like grocery and gas. Easy access to Acadia and other great parks."
United States
Scott P.
$365 nightly
The price is $398
Feb 6 - Feb 7
Total with taxes and fees
Tides' Reach - Private Waterfront King Beds
Property grounds

Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (198 reviews)
"Nice location, quiet."
United States
Michelle G.
$183 nightly
The price is $199
Feb 6 - Feb 7
Total with taxes and fees
Cozy Cabin By The Pond, Sleeps 2
Property grounds

Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
10.0 out of 10, Exceptional, (3 reviews)
"Very comfortable and convenient location. Super comfortable beds and living room furniture. Host was very quick to clean up the snow that fell overnight!"
United States
tom w.
$223 nightly
The price is $243
Feb 6 - Feb 7
Total with taxes and fees
Bright 2-Bedroom Apartment Near Downtown Thomaston
Outdoor dining

The Lewis R. French- Inn on the Harbor

The Lewis R. French- Inn on the Harbor
Stonington
9.2 out of 10, Wonderful, (9 reviews)
"Comfortable, cozy, and clean."
United States
David L.
$114 nightly
The price is $124
Feb 8 - Feb 9
Total with taxes and fees
The Lewis R. French- Inn on the Harbor
Property grounds

Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
10.0 out of 10, Exceptional, (19 reviews)
"Great location with everything we needed."
United States
Thomas P.
$347 nightly
The price is $378
Feb 6 - Feb 7
Total with taxes and fees
Waterfront Getaway Near Acadia w/ Spectacular View
Living area

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

Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach
Lincolnville
9.4 out of 10, Exceptional, (9 reviews)
"Great view. Very enjoyable stay. "
United States
Jerry C.
$207 nightly
The price is $221
Feb 6 - Feb 7
Total with taxes and fees
Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach
Property grounds

The Kittredge Cottage at East Boston Quarry

The Kittredge Cottage at East Boston Quarry
Vinalhaven
9.0 out of 10, Wonderful, (9 reviews)
"This is a beautiful cottage in a peaceful setting at the quarry. You can’t go wrong with this place, it is just lovely!!"
United States
Nicole B.
$166 nightly
The price is $180
Feb 6 - Feb 7
Total with taxes and fees
The Kittredge Cottage at East Boston Quarry
Interior

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (46 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
$228 nightly
The price is $248
Feb 8 - Feb 9
Total with taxes and fees
2 Bedroom Close to Town Home
Exterior

Eleanor's Cove - Apartment on Bayview St

Eleanor's Cove - Apartment on Bayview St
Belfast
10.0 out of 10, Exceptional, (1 review)
"Everything was absolutely perfect. I can’t think of any suggestions to make it better! "
United States
Elizabeth W.
$392 nightly
The price is $428
Feb 6 - Feb 7
Total with taxes and fees
Eleanor's Cove - Apartment on Bayview St
Interior

Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay at Spofford Lodge. The room was beyond our expectations and immaculate. Check in process was easy and great communication by Lisa. Many thanks"
United Kingdom
Richard G.
$234 nightly
The price is $251
Feb 24 - Feb 25
Total with taxes and fees
Inkwell Suite at Spofford Lodge
Smart TV

Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.4 out of 10, Exceptional, (29 reviews)
"The house was clean and well stocked. It is is located in a cute little town."
United States
Candace L.
$252 nightly
The price is $275
Feb 9 - Feb 10
Total with taxes and fees
Peaceful, Centrally Located Home with Seasonal River Views
Property grounds

Peaceful Cabin in the Woods

Peaceful Cabin in the Woods
Surry
9.6 out of 10, Exceptional, (4 reviews)
"Wonderful stay, great cabin, exactly what we needed."
United States
Amanda G.
$392 nightly
The price is $428
Mar 5 - Mar 6
Total with taxes and fees
Peaceful Cabin in the Woods
Interior

Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (85 reviews)
"Convenient location; host responsive; good towel supply. "
United States
Connie K.
$299 nightly
The price is $325
Feb 8 - Feb 9
Total with taxes and fees
Comfortable, Close to Town Home, with Oceanview.
Interior

Beautiful newly decorated and centrally located home minutes from Camden Harbor.

Beautiful newly decorated and centrally located home minutes from Camden Harbor.
Camden
10.0 out of 10, Exceptional, (6 reviews)
"Great home and location for those that want to enjoy Camden, ME. Town is a 4 minute drive, very quiet neighborhood and a well organized 3 bedroom/2 bath home with room for 2 couples or a family. Coffee service, a fire pit area and nice sized rooms. "
United States
Kevin M.
$629 nightly
The price is $686
Feb 6 - Feb 7
Total with taxes and fees
Beautiful newly decorated and centrally located home minutes from Camden Harbor.
Interior

Charming 1-bedroom apartment in Downtown Camden

Charming 1-bedroom apartment in Downtown Camden
Camden
10.0 out of 10, Exceptional, (1 review)
$175 nightly
The price is $191
Feb 25 - Feb 26
Total with taxes and fees
Charming 1-bedroom apartment in Downtown Camden
Property grounds

Charming 3-bedroom house in delightful Belfast, Maine

Charming 3-bedroom house in delightful Belfast, Maine
Belfast
10.0 out of 10, Exceptional, (3 reviews)
"Fantastic spot. Well appointed and comfortable. "
United States
Ariel B.
$415 nightly
The price is $452
Feb 6 - Feb 7
Total with taxes and fees
Charming 3-bedroom house in delightful Belfast, Maine
Living area

Unique Coastal Maine Flower Farm Stay

Unique Coastal Maine Flower Farm Stay
Belmont
9.6 out of 10, Exceptional, (16 reviews)
"Peaceful and pretty place to stay!"
United States
Sara G.
$405 nightly
The price is $442
Feb 6 - Feb 7
Total with taxes and fees
Unique Coastal Maine Flower Farm Stay
Exterior

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
$199 nightly
The price is $217
Feb 9 - Feb 10
Total with taxes and fees
Romantic Coastal Escape near Harbor
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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Top Islesboro Hotel Reviews

Rockport Harbor Hotel

Rockport Harbor Hotel

10/10 Excellent
"The hotel was beautiful and the staff outstanding."
Suzanne 2-night trip
Posted 2 days ago
Rockport Harbor Hotel

Find out more about Islesboro

Everything you need to know about Islesboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Islesboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Islesboro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Islesboro vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Islesboro. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Islesboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $108 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Islesboro rentals

At Expedia, we put the best Islesboro vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Islesboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Islesboro vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Islesboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Islesboro?

Yes, you can find vacation rentals close to the most popular points of interest in Islesboro, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Islesboro has to offer?

Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views : This vacation home rental outside of Islesboro is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Islesboro?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Islesboro stay.

What’s there to see and do in Islesboro?

While exploring the area, visit family-friendly sights like Penobscot Marine Museum, or get outside and enjoy nature at Lincolnville Beach. Warren Island State Park and Camden Hills State Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Islesboro like?

Vacation rentals are private properties where you can stay for short or long periods in Islesboro. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips.