Photo by Colleen Johnson

Islesboro Holiday 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

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Holiday Rentals in Islesboro

Water view
Trade Winds on the Bay

Trade Winds on the Bay

3.5 star property
Rockland
8.4 out of 10, Very good, (321)
"Very nice place to stay. Staff helpful and friendly."
Canada
Dan
Trade Winds on the Bay
Fridge, microwave, oven, stovetop
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.
The price is HK$740
HK$3,106 total
includes taxes & fees
8 Dec - 9 Dec
Tides' Reach - Private Waterfront King Beds
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)
"Love the cottage and very clean and quiet."
United States
Jeanne
The price is HK$771
HK$1,095 total
includes taxes & fees
8 Dec - 9 Dec
No bookings after 8/15/2024. Property sold. VRBO Thank you.
Property grounds
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 HK$531
HK$876 total
includes taxes & fees
23 Dec - 24 Dec
The Lewis R. French- Inn on the Harbor
Microwave, oven, stovetop, dishwasher
Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston

Thomaston
10.0 out of 10, Exceptional, (1)
"We had a wonderful weeklong stay while visiting family and friends in the area. We had everything we needed, and even started saying "we're going home" when leaving family.We never waited longer than 10 minutes for a reply from Jason. Everything was new, efficient, clean, and comfortable. Situated close to route 1 was especially convenient. The bedrooms on the back of the unit were cozy and quiet for sleeping. Morning coffee on the deck in the chairs was a delight.We will definitely stay again,...
United States
Lauren A.
The price is HK$747
HK$1,638 total
includes taxes & fees
8 Dec - 9 Dec
Bright 2-Bedroom Apartment Near Downtown Thomaston
Exterior
Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2

Waldo
10.0 out of 10, Exceptional, (197)
"Nice and coat cabin to come back to after long day of beach coming "
United States
Kael G.
The price is HK$841
HK$1,434 total
includes taxes & fees
8 Dec - 9 Dec
Cozy Cabin By The Pond, Sleeps 2
Interior
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.
The price is HK$1,065
HK$2,527 total
includes taxes & fees
8 Dec - 9 Dec
Bayside vista
Microwave, oven, stovetop, dishwasher
Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor

2.0 star property
Rockport
The price is HK$617
HK$1,495 total
includes taxes & fees
10 Dec - 11 Dec
Romantic Coastal Escape near Harbor
Terrace/patio
Starry Artsy Garage Loft

Starry Artsy Garage Loft

Sedgwick
9.8 out of 10, Exceptional, (28)
"Absolutely great stay. Wonderful home, wonderful host! I will be keeping this place in mind for when I come back to Maine! "
United States
Kellee M.
The price is HK$904
HK$2,266 total
includes taxes & fees
8 Dec - 9 Dec
Starry Artsy Garage Loft
Living area
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.
The price is HK$1,088
HK$1,804 total
includes taxes & fees
10 Dec - 11 Dec
Inkwell Suite at Spofford Lodge
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)
"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 HK$1,016
HK$2,949 total
includes taxes & fees
8 Dec - 9 Dec
Waterfront Getaway Near Acadia w/ Spectacular View
Interior
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
The price is HK$693
HK$1,638 total
includes taxes & fees
11 Dec - 12 Dec
Apt 1 Studio apartments in downtown Stonington
Property grounds
Glamping at Maine Water Buffalo Farm

Glamping at Maine Water Buffalo Farm

1.0 star property
Appleton
10.0 out of 10, Exceptional, (2)
"Really great place….very thoughtful set up for us to enjoy."
United States
Peter P.
The price is HK$1,082
HK$1,349 total
includes taxes & fees
31 Dec - 1 Jan 2026
Glamping at Maine Water Buffalo Farm
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 HK$1,259
HK$1,999 total
includes taxes & fees
10 Dec - 11 Dec
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

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.
The price is HK$973
HK$2,138 total
includes taxes & fees
8 Dec - 9 Dec
Peaceful, Centrally Located Home with Seasonal River Views
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, (2)
"Exactly as advertised."
United States
Theresa
The price is HK$1,915
HK$3,844 total
includes taxes & fees
5 Jan - 6 Jan 2026
Charming 3-bedroom house with a Pond View/pet friendly
TV
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.
The price is HK$806
HK$1,930 total
includes taxes & fees
8 Dec - 9 Dec
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)
"Wonderful stay, great cabin, exactly what we needed."
United States
Amanda G.
The price is HK$1,513
HK$3,372 total
includes taxes & fees
5 Jan - 6 Jan 2026
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, (84)
"This our second year and this property continues to be excellent. The proper is clean and comfortable and convenient to town or the each. The view from the porch is always stunning. The owner is very easy to work with. "
United States
Amy F.
The price is HK$1,226
HK$2,592 total
includes taxes & fees
8 Dec - 9 Dec
Comfortable, Close to Town Home, with Oceanview.
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

Lincolnville
9.4 out of 10, Exceptional, (9)
"Such a beautiful property with an amazing view! "
United States
Katie F.
The price is HK$1,275
HK$2,042 total
includes taxes & fees
17 Dec - 18 Dec
Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach
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

Trade Winds on the Bay

Trade Winds on the Bay

10/10 Excellent
"The room was clean, I had trouble with the TV and the desk clerk was extremely helpful. He even came to our room and then he asked us if it was okay for him to enter the room to check out the TV. Definitely will be back.. "
Michael 1-night trip
Posted 2 days ago
Trade Winds on the Bay

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 holiday rental in Islesboro?

Yes, there are holiday rentals close to the most popular sights in Islesboro, or you can select a more secluded option if you're looking for a relaxing stay.

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

Island log home in Maine with ocean views: This highly rated holiday home rental in Islesboro offers a fireplace, a patio and a BBQ 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 holiday with amenities such as a garden.

How many holiday rentals are there in Islesboro?

With 7 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Islesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islesboro. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for families.