Islesboro Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

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, (341 reviews)
"Very nice place "
United States
Robert
Trade Winds on the Bay
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.
The price is ￥18,738
￥31,147 total
includes taxes & fees
Feb 12 - Feb 13
Cozy Cabin By The Pond, Sleeps 2
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.
The price is ￥14,942
￥63,413 total
includes taxes & fees
Feb 13 - Feb 14
Tides' Reach - Private Waterfront King Beds
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.
The price is ￥21,731
￥51,090 total
includes taxes & fees
Feb 12 - Feb 13
Bayside vista
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.
The price is ￥24,562
￥39,346 total
includes taxes & fees
Mar 10 - Mar 11
Inkwell Suite at Spofford Lodge
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.
The price is ￥30,356
￥66,959 total
includes taxes & fees
Mar 11 - Mar 12
Peaceful Cabin in the Woods
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.
The price is ￥18,738
￥37,955 total
includes taxes & fees
Feb 14 - Feb 15
Bright 2-Bedroom Apartment Near Downtown Thomaston
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.
The price is ￥24,594
￥50,296 total
includes taxes & fees
Feb 12 - Feb 13
Comfortable, Close to Town Home, with Oceanview.
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.
The price is ￥21,642
￥60,694 total
includes taxes & fees
Feb 12 - Feb 13
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.
The price is ￥20,748
￥34,508 total
includes taxes & fees
Feb 12 - Feb 13
Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach
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)
"Made wonderful memories and really enjoyed the beautiful oceanfront town of Stonington."
United States
Elizabeth P.
The price is ￥12,297
￥19,361 total
includes taxes & fees
Feb 12 - Feb 13
The Lewis R. French- Inn on the Harbor
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.
The price is ￥33,237
￥70,610 total
includes taxes & fees
Feb 12 - Feb 13
Charming 3-bedroom house in delightful Belfast, Maine
Interior

Charming 1-bedroom apartment in Downtown Camden

Charming 1-bedroom apartment in Downtown Camden
Camden
10.0 out of 10, Exceptional, (2 reviews)
"PERFECT! Location is great and walkable to everything. Super comfortable with every amenity you could need. Host was kind and very responsive. We'll be back for sure!"
United States
Jen Olendorf P.
The price is ￥16,083
￥29,785 total
includes taxes & fees
Feb 12 - Feb 13
Charming 1-bedroom apartment in Downtown Camden
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.
The price is ￥19,519
￥42,892 total
includes taxes & fees
Feb 12 - Feb 13
Peaceful, Centrally Located Home with Seasonal River Views
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.
The price is ￥16,162
￥38,723 total
includes taxes & fees
Feb 12 - Feb 13
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.
The price is ￥34,103
￥66,788 total
includes taxes & fees
Feb 12 - Feb 13
Eleanor's Cove - Apartment on Bayview St
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.
The price is ￥34,993
￥66,056 total
includes taxes & fees
Feb 12 - Feb 13
Unique Coastal Maine Flower Farm Stay
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.
The price is ￥17,567
￥28,170 total
includes taxes & fees
Feb 12 - Feb 13
The Kittredge Cottage at East Boston Quarry
Exterior

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
The price is ￥15,459
￥33,871 total
includes taxes & fees
Feb 24 - Feb 25
Romantic Coastal Escape near Harbor
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.
The price is ￥54,653
￥107,059 total
includes taxes & fees
Feb 12 - Feb 13
Beautiful newly decorated and centrally located home minutes from Camden 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 room was beautiful and the atmosphere of the entire hotel was amazing ."
Tyler 2-night trip
Posted 2 days ago
Rockport Harbor Hotel

Find out more about Islesboro

Search for holiday rentals in Islesboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Islesboro using one of the methods below:

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Look no further and take a look at our great range of rental properties in Islesboro!

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?

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets: This vacation home rental outside of Islesboro offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable 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 books.

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.