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Islesboro Vacation Rentals

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Dec 21 - Dec 22
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Dec 22 - Dec 23
Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4

Our top choices for Islesboro vacation rentals

Water view
Trade Winds on the Bay

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.4 out of 10, Very Good, (323)
"Very nice place to stay. Staff helpful and friendly."
Canada
Dan
$99 nightly
The price is $108
Dec 24 - Dec 25
Total with taxes and fees
Trade Winds on the Bay
Property grounds
The Lewis R. French- Inn on the Harbor

The Lewis R. French- Inn on the Harbor

The Lewis R. French- Inn on the Harbor
Stonington
9.2 out of 10, Wonderful, (9)
"Comfortable, cozy, and clean."
United States
David L.
$103 nightly
The price is $113
Dec 23 - Dec 24
Total with taxes and fees
The Lewis R. French- Inn on the Harbor
Fridge, oven, stovetop, dishwasher
No bookings after 8/15/2024. Property sold. VRBO Thank you.

No bookings after 8/15/2024. Property sold. VRBO Thank you.

No bookings after 8/15/2024. Property sold. VRBO Thank you.
Searsmont
10.0 out of 10, Exceptional, (5)
"Love the cottage and very clean and quiet."
United States
Jeanne
$129 nightly
The price is $141
Dec 22 - Dec 23
Total with taxes and fees
No bookings after 8/15/2024. Property sold. VRBO Thank you.
Exterior
Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (197)
"Just perfect accommodations "
United States
Jeffrey J.
$170 nightly
The price is $185
Dec 22 - Dec 23
Total with taxes and fees
Cozy Cabin By The Pond, Sleeps 2
Fridge, microwave, oven, stovetop
Tides' Reach - Private Waterfront King Beds

Tides' Reach - Private Waterfront King Beds

Tides' Reach - Private Waterfront King Beds
Orland
9.8 out of 10, Exceptional, (23)
"Great stay! Lots of space for everyone. Great kitchen to cook in. Loved sitting on the porch rockers every morning for coffee. Good size for a family. The two kings in one room is great if you have lots of kids. "
United States
Cass R.
$409 nightly
The price is $445
Dec 22 - Dec 23
Total with taxes and fees
Tides' Reach - Private Waterfront King Beds
Microwave, oven, stovetop, dishwasher
Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
10.0 out of 10, Exceptional, (2)
"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.
$196 nightly
The price is $214
Dec 27 - Dec 28
Total with taxes and fees
Bright 2-Bedroom Apartment Near Downtown Thomaston
Living area
Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (14)
"Property was very nice, clean and Lisa our host was very nice and helpful. Great place, highly recommend!"
United States
brian g.
$237 nightly
The price is $253
Jan 20 - Jan 21, 2026
Total with taxes and fees
Inkwell Suite at Spofford Lodge
Interior
Bayside vista

Bayside vista

Bayside vista
Bucksport
10.0 out of 10, Exceptional, (15)
"We loved our stay in Bucksport. The apartment was comfortable, clean and had everything we needed - and the view could not be beat! "
United States
Allison M.
$281 nightly
The price is $307
Jan 3 - Jan 4, 2026
Total with taxes and fees
Bayside vista
Property grounds
Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
10.0 out of 10, Exceptional, (19)
"The home was just as advertised and just what we wanted. "
United States
Joe B.
$347 nightly
The price is $378
Dec 22 - Dec 23
Total with taxes and fees
Waterfront Getaway Near Acadia w/ Spectacular View
Microwave, oven, stovetop, dishwasher
Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
2.0 star property
Rockport
$176 nightly
The price is $192
Jan 3 - Jan 4, 2026
Total with taxes and fees
Romantic Coastal Escape near Harbor
Interior
Apt 1 Studio apartments in downtown Stonington

Apt 1 Studio apartments in downtown Stonington

Apt 1 Studio apartments in downtown Stonington
Stonington
10.0 out of 10, Exceptional, (75)
"good place to stay"
United States
Robert
$191 nightly
The price is $208
Dec 22 - Dec 23
Total with taxes and fees
Apt 1 Studio apartments in downtown Stonington
Interior
Abacus Suite at Spofford Lodge

Abacus Suite at Spofford Lodge

Abacus Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (3)
"Terrific suite!! Perfectly appointed, quiet and serene. Couldn't ask for better hosts. Have to come back and stay soon! Thank you for your kind and generous spirit and for sharing your beautiful restoration with me."
United States
Leslie S.
$265 nightly
The price is $284
Jan 20 - Jan 21, 2026
Total with taxes and fees
Abacus Suite at Spofford Lodge
Fridge, microwave, oven, stovetop
Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.4 out of 10, Exceptional, (29)
"Amazing little house tucked away close to the river. It was very clean and nicely furnished. I had a great time staying here and it was very close to downtown Thomaston."
United States
Avery W.
$252 nightly
The price is $275
Dec 22 - Dec 23
Total with taxes and fees
Peaceful, Centrally Located Home with Seasonal River Views
Interior
2 Bedroom Close to Town Home

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (45)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
$228 nightly
The price is $248
Jan 4 - Jan 5, 2026
Total with taxes and fees
2 Bedroom Close to Town Home
1 bedroom, iron/ironing board, internet, bed sheets
Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach

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)
"Great view. Very enjoyable stay. "
United States
Jerry C.
$207 nightly
The price is $221
Dec 22 - Dec 23
Total with taxes and fees
Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach
Dining
Charming 3-bedroom house in delightful Belfast, Maine

Charming 3-bedroom house in delightful Belfast, Maine

Charming 3-bedroom house in delightful Belfast, Maine
Belfast
10.0 out of 10, Exceptional, (3)
"Fantastic spot. Well appointed and comfortable. "
United States
Ariel B.
$415 nightly
The price is $452
Dec 22 - Dec 23
Total with taxes and fees
Charming 3-bedroom house in delightful Belfast, Maine
Interior
Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (85)
"Convenient location; host responsive; good towel supply. "
United States
Connie K.
$306 nightly
The price is $333
Jan 2 - Jan 3, 2026
Total with taxes and fees
Comfortable, Close to Town Home, with Oceanview.
Exterior
Peaceful Cabin in the Woods

Peaceful Cabin in the Woods

Peaceful Cabin in the Woods
Surry
9.6 out of 10, Exceptional, (4)
"Wonderful stay, great cabin, exactly what we needed."
United States
Amanda G.
$396 nightly
The price is $432
Jan 19 - Jan 20, 2026
Total with taxes and fees
Peaceful Cabin in the Woods
Living area
Unique Coastal Maine Flower Farm Stay

Unique Coastal Maine Flower Farm Stay

Unique Coastal Maine Flower Farm Stay
Belmont
9.6 out of 10, Exceptional, (16)
"Peaceful and pretty place to stay!"
United States
Sara G.
$384 nightly
The price is $419
Dec 22 - Dec 23
Total with taxes and fees
Unique Coastal Maine Flower Farm Stay
Dining
Beautiful newly decorated and centrally located home minutes from Camden Harbor.

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, (4)
"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.
$515 nightly
The price is $561
Dec 27 - Dec 28
Total with taxes and fees
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

The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

10/10 Excellent
"Plenty of room, quiet, and the staff were very kind "
Edith 1-night trip
Posted 21 hours ago
The Country Inn at Camden Rockport

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?

Island log home in Maine with ocean views: This highly rated vacation home rental in Islesboro offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a garden.

How many vacation rentals are there in Islesboro?

With 6 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.