Photo by Colleen Johnson

Islesboro Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Islesboro

TV
Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston

Thomaston
The price is ￥14,728
￥31,940 total
includes taxes & fees
Nov 12 - Nov 13
Bright 2-Bedroom Apartment Near Downtown Thomaston
Exterior
Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor

2.0 star property
Rockport
The price is ￥20,742
￥40,168 total
includes taxes & fees
Nov 16 - Nov 17
Romantic Coastal Escape near Harbor
Water view
Trade Winds on the Bay

Trade Winds on the Bay

3.5 star property
Rockland
8.4 out of 10, Very Good, (311)
"Basic room , clean and perfect for our stay. "
United States
Deborah
Trade Winds on the Bay
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.

Searsmont
10.0 out of 10, Exceptional, (5)
"Perfect fit for our trip. Everything we needed in this cute little home."
United States
Carol F.
The price is ￥15,189
￥21,573 total
includes taxes & fees
Nov 12 - Nov 13
No bookings after 8/15/2024. Property sold. VRBO Thank you.
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)
"Comfortable, cozy, and clean."
United States
David L.
The price is ￥16,109
￥26,756 total
includes taxes & fees
Nov 12 - Nov 13
The Lewis R. French- Inn on the Harbor
Exterior
Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2

Waldo
10.0 out of 10, Exceptional, (195)
"We enjoyed the cabin! The kitchen had everything we needed. It was fun exploring the area, and thanks to the hosts for the tip on where to go with our paddle boards! "
United States
Marta v.
The price is ￥18,410
￥30,435 total
includes taxes & fees
Dec 1 - Dec 2
Cozy Cabin By The Pond, Sleeps 2
Living area
Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge

Bucksport
10.0 out of 10, Exceptional, (14)
"Beautiful relaxing stay with very easy check in process. Decorated superbly!"
United States
Mark
The price is ￥24,302
￥39,010 total
includes taxes & fees
Dec 4 - Dec 5
Inkwell Suite at Spofford Lodge
Smart TV, fireplace
Charming 3-bedroom house with a Pond View/pet friendly

Charming 3-bedroom house with a Pond View/pet friendly

Belfast
10.0 out of 10, Exceptional, (1)
"Exactly as advertised."
United States
Theresa
The price is ￥27,616
￥63,045 total
includes taxes & fees
Nov 12 - Nov 13
Charming 3-bedroom house with a Pond View/pet friendly
1 bedroom, WiFi, bed sheets
Apt 1 Studio apartments in downtown Stonington

Apt 1 Studio apartments in downtown Stonington

Stonington
10.0 out of 10, Exceptional, (75)
"Great location, very comfortable and very clean."
United States
Judith
The price is ￥13,654
￥31,940 total
includes taxes & fees
Nov 12 - Nov 13
Apt 1 Studio apartments in downtown Stonington
Terrace/patio
Starry Artsy Garage Loft

Starry Artsy Garage Loft

Sedgwick
9.8 out of 10, Exceptional, (28)
"Traveling with family and friend. Great place to relax and decompress after spending the day at the exploring Acadia nation park. "
United States
Ernest D.
The price is ￥17,812
￥44,667 total
includes taxes & fees
Nov 14 - Nov 15
Starry Artsy Garage Loft
Property grounds
Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View

Deer Isle
10.0 out of 10, Exceptional, (18)
"Super easy place in a wonderful location - clean and easy to get into - would definitely stay here again if coming back. Views were wonderful!"
United States
Steven F.
The price is ￥20,021
￥57,945 total
includes taxes & fees
Nov 12 - Nov 13
Waterfront Getaway Near Acadia w/ Spectacular View
Interior
Bayside vista

Bayside vista

Bucksport
10.0 out of 10, Exceptional, (14)
"Cozy place with modern amenities and a fantastic view. The coffee and tea bar is wonderful and thoughtfully prepared. The kitchen is perfectly stocked and fun to cook in. The best part was lounging on the couch, looking at the penobscot narrows, while enjoying the peaceful quiet with my partner while we knitted. Thank you for the relaxing vacation."
United States
Kevin K.
The price is ￥19,745
￥48,111 total
includes taxes & fees
Nov 17 - Nov 18
Bayside vista
Interior
Lone Star Lodge - Newly Renovated Studio

Lone Star Lodge - Newly Renovated Studio

Northport
10.0 out of 10, Exceptional, (1)
"I loved the Lone Star! Everything was perfect, it was very clean, very comfortable and stylish. I loved the location in Northport which is very convenient to all of the Central Coast."
United States
Evelyn F.
The price is ￥25,775
￥48,329 total
includes taxes & fees
Nov 12 - Nov 13
Lone Star Lodge - Newly Renovated Studio
Fridge, microwave, oven, stovetop
Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views

Thomaston
9.4 out of 10, Exceptional, (29)
"The house was clean and close to many things to do. I would stay there again."
United States
Jeff T.
The price is ￥19,178
￥41,975 total
includes taxes & fees
Nov 12 - Nov 13
Peaceful, Centrally Located Home with Seasonal River Views
Interior
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.
The price is ￥27,846
￥43,375 total
includes taxes & fees
Dec 4 - Dec 5
Abacus Suite at Spofford Lodge
TV
2 Bedroom Close to Town Home

2 Bedroom Close to Town Home

Thomaston
9.0 out of 10, Wonderful, (45)
"We found this property modest and functional, clean and convenient. It was a good base for our family weekend. "
United States
Stanley
The price is ￥15,879
￥37,878 total
includes taxes & fees
Nov 12 - Nov 13
2 Bedroom Close to Town Home
Exterior
Peaceful Cabin in the Woods

Peaceful Cabin in the Woods

Surry
9.6 out of 10, Exceptional, (4)
"This property fit our needs perfectly. The location was an easy ride to town and just far enough from Acadia to escape the crowds."
United States
William D.
The price is ￥29,825
￥66,290 total
includes taxes & fees
Dec 9 - Dec 10
Peaceful Cabin in the Woods
Interior
New Colonial One Mile from Camden Harbor

New Colonial One Mile from Camden Harbor

2.0 star property
Camden
10.0 out of 10, Exceptional, (11)
"I cannot praise these hosts or the property enough! From the moment we booked until the moment we drove away a week later, our stay was seamless and exceeded our expectations. The house was so clean, well appointed and organized, it would surprise me if we weren’t the first people to ever sleep there. The space is laid out perfectly with two large common spaces, everything you can possibly need for a kitchen, bedding, linens, games, televisions in every room, a grill, a hose to spray your sandy...
United States
Barbara P.
The price is ￥29,150
￥78,430 total
includes taxes & fees
Nov 12 - Nov 13
New Colonial One Mile from Camden Harbor
Exterior
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature

SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature

Penobscot
10.0 out of 10, Exceptional, (6)
The price is ￥33,001
￥68,413 total
includes taxes & fees
Nov 12 - Nov 13
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
Living area
Unique Coastal Maine Flower Farm Stay

Unique Coastal Maine Flower Farm Stay

Belmont
9.6 out of 10, Exceptional, (16)
"The rental is a spacious 2-bedroom apartment overlooking the grounds, greenhouses, and fields of the unique Leafsong farm, out in the quiet and leafy countryside southwest of Belfast. You may meet the peacocks, sheep, mule, and horse who also call this place home. Many treasures to be found at the flower shop on the premises."
United States
David B.
The price is ￥31,620
￥64,232 total
includes taxes & fees
Nov 18 - Nov 19
Unique Coastal Maine Flower Farm Stay
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Islesboro Hotel Reviews

Hampton Inn & Suites Rockland

Hampton Inn & Suites Rockland

10/10 Excellent
"Quiet, convenient "
ken 2-night trip
Posted 2 days ago
Hampton Inn & Suites Rockland

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:

  • View our selection of featured holiday rentals in Islesboro
  • Use the map to find apartments and other holiday homes in the Islesboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Islesboro while they last

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?

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 8 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 Perry's Nut House, 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.