A calm lake with a dock, boats, and a forested shoreline.

Islesboro Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Islesboro holiday rentals

Lobby sitting area

1. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (527 reviews)
"Everything was clean, easy check in process and convenient location, walking distance to multiple restaurants."
United States
Bill
The price is AU$180
includes taxes & fees
1 Nov - 2 Nov
Trade Winds on the Bay
A cozy bedroom with a bed, a large window, and a view of the outdoors.

2. Lone Star Lodge - Newly Renovated Studio

Lone Star Lodge - Newly Renovated Studio
Northport
10.0 out of 10, Exceptional, (1 review)
"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 AU$529
includes taxes & fees
28 Oct - 29 Oct
Lone Star Lodge - Newly Renovated Studio
A two-story house with a front porch, a chimney, and a garage.

3. Cozy cottage -Close to Downtown Camden!

Cozy cottage -Close to Downtown Camden!
Camden
9.6 out of 10, Exceptional, (35 reviews)
"This property was clean, the kitchen was well appointed, it was close to downtown and the beds were very comfortable. I would stay here again or reccomend it to others."
United States
Abby S.
The price is AU$739
includes taxes & fees
29 Oct - 30 Oct
Cozy cottage -Close to Downtown Camden!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

4. 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, (22 reviews)
"absolutely stunning place convenient location! we loved every single comfy detail! all of our beds were so comfortable and clean! my family of four thought it was so wonderful!"
United States
Ashley G.
The price is AU$729
includes taxes & fees
28 Oct - 29 Oct
Beautiful newly decorated and centrally located home minutes from Camden Harbor.
A deck with a table and chairs, a potted plant, and a view of a lake.

5. Rustic luxury waterfront apartment, 2 decks, kayaks, fireplace, peace & beauty.

Rustic luxury waterfront apartment, 2 decks, kayaks, fireplace, peace & beauty.
Penobscot
10.0 out of 10, Exceptional, (1 review)
"None of us wanted to leave. The Roost will be our first choice whenever we return. Barb and Les made us feel right at home. We had deer and turkey visit the yard and the bird watching from the dock was excellent. I can't find a single thing to improve upon here. "
United States
Cindy C.
The price is AU$578
includes taxes & fees
28 Oct - 29 Oct
Rustic luxury waterfront apartment, 2 decks, kayaks, fireplace, peace & beauty.
A wooden deck with outdoor seating, a fire pit, and a view of a harbor with boats and buildings.

6. J & E Riggins - Inn on the Harbor

J & E Riggins - Inn on the Harbor
Stonington
10.0 out of 10, Exceptional, (11 reviews)
"Fab place!"
United States
Thomas K.
J & E Riggins - Inn on the Harbor
A wooden dock leading to a beach with a picnic table and chairs, surrounded by greenery.

7. Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
9.8 out of 10, Exceptional, (27 reviews)
"Great location with everything we needed."
United States
Thomas P.
The price is AU$554
includes taxes & fees
3 Nov - 4 Nov
Waterfront Getaway Near Acadia w/ Spectacular View
A spacious room with a large window, a wicker sofa, a patterned rug, and a wooden deck with a view of the outdoors.

8. Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway

Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
Rockport
10.0 out of 10, Exceptional, (74 reviews)
"Amazing views and the privacy was just awesome. Not too far away from Camden, Rockport and rockland.."
United States
Tracey N.
The price is AU$643
includes taxes & fees
28 Oct - 29 Oct
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

9. Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (37 reviews)
"This was such a super cute place. Great little get away. Very clean! I would definitely recommend this place if you are in the area!"
United States
Beth
The price is AU$219
includes taxes & fees
5 Nov - 6 Nov
Simplicity-Just what you need! STR24-20
A wooden cabin with a door and window, surrounded by dense forest.

10. Restful Maine Cabin 6 • Fire Pit • Sauna • Beach

Restful Maine Cabin 6 • Fire Pit • Sauna • Beach
Stockton Springs
10.0 out of 10, Exceptional, (12 reviews)
"The cabin we stayed in was beautiful and very clean. Our dog even loved the stay, we will definitely be back!"
United States
Marissa
The price is AU$371
includes taxes & fees
3 Nov - 4 Nov
Restful Maine Cabin 6 • Fire Pit • Sauna • Beach
A hotel room with a wooden paneled wall, a bed with a green bedspread, two white armchairs, a wooden nightstand with a lamp, and framed artwork on the wall.

11. Apt 1 Studio apartment in downtown Stonington

Apt 1 Studio apartment in downtown Stonington
Stonington
9.8 out of 10, Exceptional, (86 reviews)
"Nice place. Very cozy"
United States
Mark
The price is AU$372
includes taxes & fees
29 Oct - 30 Oct
Apt 1 Studio apartment in downtown Stonington
A two-story house with a front porch and solar panels on the roof, surrounded by trees and a lake with boats.

12. Eleanor's Cove - Apartment on Bayview St

Eleanor's Cove - Apartment on Bayview St
Belfast
10.0 out of 10, Exceptional, (2 reviews)
"Great location with beautiful view of the bay from back deck. Very clean and comfortable. Walkable to wonderful little town with cute shops and many great restaurants. Easy drive to Acadia. Highly recommend"
United States
Sandra C.
The price is AU$695
includes taxes & fees
29 Oct - 30 Oct
Eleanor's Cove - Apartment on Bayview St
A wooden deck with wicker rocking chairs overlooking a lake.

13. 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, (9 reviews)
"This cottage was truly lovely, comfortable and with an absolutely beautiful view. Barbara was an excellent host. I intend to book here again five star for sure."
United States
Mike C.
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
A patio with a table and chairs, surrounded by a grassy lawn and a wooded area.

14. Country Charm: Cozy getaway in delightful Searsport

Country Charm: Cozy getaway in delightful Searsport
Searsport
9.4 out of 10, Exceptional, (35 reviews)
"Super clean, and the listing is accurate. We enjoyed our stay."
United States
Leslie P.
Country Charm: Cozy getaway in delightful Searsport
A covered porch with a grill, a potted plant, and a small table.

15. Cheerful Two Bedroom Cabin - 10 minutes to Camden!

Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
9.8 out of 10, Exceptional, (16 reviews)
"Looking for a quick get-away - this is the place! The cabins are so cute and comfortable. Plenty of room for a couple or a family. It was our second time there and will definitely return!"
United States
Patricia T.
The price is AU$789
includes taxes & fees
28 Oct - 29 Oct
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
A living room with a sofa, armchair, TV, bookshelf, and a window with blinds.

16. Phoenix Nest - Downtown Apartment in Belfast

Phoenix Nest - Downtown Apartment in Belfast
Belfast
9.0 out of 10, Wonderful, (2 reviews)
"I just felt like we were paying City prices for a small town really cute little town but whose I can say Manhattan for the same price"
United States
Tom K.
The price is AU$510
includes taxes & fees
28 Oct - 29 Oct
Phoenix Nest - Downtown Apartment in Belfast
A small cabin with a porch, surrounded by lush greenery and a pond.

17. Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (235 reviews)
"Very nice and cozy stay and the hosts were very kind and helpful. Highly recommend!"
United States
Skand
The price is AU$286
includes taxes & fees
17 Nov - 18 Nov
Cozy Cabin By The Pond, Sleeps 2
A room with a large window offering a view of a snowy landscape and a body of water.

18. Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (103 reviews)
"We weren’t even there for 24 hours. It was a great stop on the coast. Close to Rockland and a nice view of the ocean."
United States
Ted H.
The price is AU$481
includes taxes & fees
10 Nov - 11 Nov
Comfortable, Close to Town Home, with Oceanview.
A wooden cabin-style kitchen with a central dining table, wooden cabinets, and a hanging light fixture.

19. Relaxing Two Bedroom Cabin - 10 minutes to Camden!

Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
8.4 out of 10, Very good, (6 reviews)
"We booked this place for Memorial Weekend, and drove into Camden to explore the town. Host was so friendly and responsive, the cabin was so clean and quaint/cute, loved the location that we go that cabin feel but could drive a short distance to get into town/harbor, and overall had a great time! "
United States
Kimberly
The price is AU$789
includes taxes & fees
28 Oct - 29 Oct
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
A wooden deck with two chairs and a view of a forested landscape.

20. Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House

Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House
Brooklin
9.8 out of 10, Exceptional, (6 reviews)
"The space was perfect for us. It was lovely and super convenient both for classes at WoodenBoat School and hikes at Acadia."
United States
Strephon T.
The price is AU$420
includes taxes & fees
28 Oct - 29 Oct
Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House
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

Trade Winds on the Bay

Trade Winds on the Bay

8/10 Good
"Nice place. It was fine. The Host was very helpful."
Rose 1-night trip
Posted 10 hours ago
Trade Winds on the Bay

Find out more about Islesboro

Everything you need to know about Islesboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Islesboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Islesboro holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Islesboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Islesboro holiday rentals we have selected for you start as low as AU$180 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Islesboro rentals

At Expedia, we put the best Islesboro holiday 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 holiday.

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. 

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 9 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.