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

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

Holiday Rentals in Islesboro

Fridge, microwave, oven, stovetop
Island log home in Maine with ocean views

Island log home in Maine with ocean views

Islesboro
10.0 out of 10, Exceptional, (86)
"Literally could not ask for more. Absolutely ideal place to stay. Clean, cared for, and exactly as pictured. Serene location, close to everything. "
United States
Deby C.
Island log home in Maine with ocean views
Water view
Trade Winds on the Bay

Trade Winds on the Bay

3.5 star property
Rockland
8.4 out of 10, Very good, (312)
"Basic room , clean and perfect for our stay. "
United States
Deborah
Trade Winds on the Bay
Exterior
Point Lookout

Point Lookout

3.0 star property
Lincolnville
9.8 out of 10, Exceptional, (11)
"A nice quiet getaway "
United States
Camilla
Point Lookout
Property grounds
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

Lincolnville
8.0 out of 10, Very good, (11)
"Very remote-no cell service so communication with Host was nonexistent. So, we chose not to risk a stay-not safe for us!"
United States
Morris
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Outdoor spa tub
Gorgeous Waterfront Estate In Historic Bayside

Gorgeous Waterfront Estate In Historic Bayside

Northport
10.0 out of 10, Exceptional, (76)
"We had a family reunion here. House is extraordinarily well equipped. Owner was very responsive to any request or question. Photos are accurate. Loved our visit."
United States
Paul c.
Gorgeous Waterfront Estate In Historic Bayside
Interior
Cozy Cabin on Blue Hill Farm

Cozy Cabin on Blue Hill Farm

Blue Hill
9.8 out of 10, Exceptional, (27)
"Great place! My partner and I had so much fun staying here. The location is the best and in a convenient spot. Sean was absolutely amazing! "
United States
Stephanie T.
Cozy Cabin on Blue Hill Farm
Interior
35 Mi to Acadia: Rustic Retreat in Orland!

35 Mi to Acadia: Rustic Retreat in Orland!

2.0 star property
Orland
6.0 out of 10, (2)
"Exactly what you think of a cabin in the Maine woods. Close to Bucksport. No wifi. Only got one channel on the rabbit ears for the TV, but many movies available to use on the dvd player. Dark outside at night. Quick response from property manager. Would stay there again. "
United States
Jayson
35 Mi to Acadia: Rustic Retreat in Orland!
Interior
PINE LODGE NORTHPORT MAINE FAMILY REUNIONS, WEDDING,RETREAT ACADIA BAR HARBOR

PINE LODGE NORTHPORT MAINE FAMILY REUNIONS, WEDDING,RETREAT ACADIA BAR HARBOR

Northport
9.6 out of 10, Exceptional, (55)
"5.5 STARS!Terra was a most gracious host. Her property is amazing for family gatherings. The property has so many different activities to do. The space is wide open with ample seating indoor and outdoor. Both indoor and outdoor fireplace. She was extremely responsive to inquiries and very timely. She helped us ahead of time by providing information for catering services while on property. She was there at our check-in process to answer any questions that we might have. "
United States
James W.
The price is HK$12,593
HK$30,773 total
includes taxes & fees
29 Nov - 30 Nov
PINE LODGE NORTHPORT MAINE FAMILY REUNIONS, WEDDING,RETREAT ACADIA BAR HARBOR
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 HK$1,602
HK$3,253 total
includes taxes & fees
19 Nov - 20 Nov
Unique Coastal Maine Flower Farm Stay
Exterior
Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2

Waldo
10.0 out of 10, Exceptional, (195)
"Delightful cottage. "
United States
robert s.
The price is HK$932
HK$1,550 total
includes taxes & fees
16 Dec - 17 Dec
Cozy Cabin By The Pond, Sleeps 2
Marina
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town

Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town

Camden
9.0 out of 10, Wonderful, (78)
"This was a very nice house, including the apartment, for our group of 13. There was plenty of room for everyone and it’s in a great location. The kitchens could be better stocked with dishes for a house that holds large groups. "
United States
Pamela S.
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Exterior
Waterfront cottage with deep water dock, ocean front.

Waterfront cottage with deep water dock, ocean front.

Belfast
9.8 out of 10, Exceptional, (106)
"This was the cutest cottage for our first trip to Maine! We loved taking our dog for walks on the trails behind the house. There was plenty of wildlife and beauty right behind the house. This was the best place for birdwatching! We could hear the loons from our window at night, and we saw them in the lake a few times. The cottage itself was beautifully decorated, spotless, and had everything we needed for cooking dinners. The host, Jon, was quick to respond to our questions and made the whole...
United States
Courtney B.
Waterfront cottage with deep water dock, ocean front.
Interior
Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Owls Head
9.6 out of 10, Exceptional, (83)
"Our family enjoyed staying in this cute cottage. The host was very helpful and quick to respond when we had trouble getting into the location upon arrival. We had a great time hanging out on the front porch and relaxing in the evening. We definitely wished we could have stayed another night or two to relax and explore the area a little more, maybe sometime in the future."
United States
Laura C.
The price is HK$1,224
HK$2,588 total
includes taxes & fees
16 Nov - 17 Nov
Comfortable, Close to Town Home, with Oceanview.
Property grounds
Morning sun, coffee in hand, a good book and so much more...

Morning sun, coffee in hand, a good book and so much more...

Camden
9.8 out of 10, Exceptional, (90)
"Lovely property, cozy and nice location. Nice property owner."
United States
DeAnn J.
Morning sun, coffee in hand, a good book and so much more...
Property grounds
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range

Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range

South Thomaston
9.2 out of 10, Wonderful, (20)
"Great place for a romantic get a way. Great lobster just down the road."
United States
G Allen H.
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
Marina
Oceanville Oasis on the Peaceful Island

Oceanville Oasis on the Peaceful Island

Stonington
9.8 out of 10, Exceptional, (6)
"Great property. Clean, quiet, great kitchen. Exceptional host with great communication. A real find if you are traveling to Deer Isle. We will be going back!"
United States
Stephen
Oceanville Oasis on the Peaceful Island
Interior
Pet-friendly Prospect Apartment: 7 Mi to Beach!

Pet-friendly Prospect Apartment: 7 Mi to Beach!

3.0 star property
Stockton Springs
7.0 out of 10, Good, (2)
"We just spent 3 nights here over 4th of July weekend. Overall, the property was nice, clean, and comfortable; however, it was advertised as sleeping 4 people when it only sleeps 2. There is only one bedroom with a double bed and that’s it. There’s a couch in the living room, but it’s NOT a sleeper. We booked this place as there were 4 of us (myself and my boyfriend as well as my parents). We ended up having to get my parents a room at a nearby hotel as there was no place for them to sleep...
United States
Johanna
Pet-friendly Prospect Apartment: 7 Mi to Beach!
Fridge, microwave, oven, stovetop
Newly renovated 2-bedroom cottage conveniently located with all the amenities!

Newly renovated 2-bedroom cottage conveniently located with all the amenities!

2.0 star property
Camden
9.8 out of 10, Exceptional, (12)
"It is conveniently located. Very clean. Nice big yard."
United States
Joseph
Newly renovated 2-bedroom cottage conveniently located with all the amenities!
Beach towels
Owls Head Village Post Office

Owls Head Village Post Office

Owls Head
10.0 out of 10, Exceptional, (167)
"We have stayed here several times and coming back just brings us joy. Mornings on the balcony with coffee and a book are the best. Access to kayaks and food right next door just can’t be beat. "
United States
Sarah W.
Owls Head Village Post Office
Property grounds
Newly built quiet studio apartment near Reversing Falls

Newly built quiet studio apartment near Reversing Falls

Blue Hill
9.8 out of 10, Exceptional, (45)
"Great spot! The hosts were awesome! "
United States
Beowulf U.
Newly built quiet studio apartment near Reversing Falls
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

Fireside Inn & Suites - Belfast

Fireside Inn & Suites - Belfast

10/10 Excellent
"The little gem has everything you need, including wonderful views of the ocean. Rooms were neat and clean. Staff was warm and welcoming. "
Michelle 1-night trip
Posted 1 day ago
Fireside Inn & Suites - Belfast

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.