Photo by Colleen Johnson

Holiday Rentals in Islesboro

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Check prices for these dates

Our top choices for Islesboro holiday rentals

1. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (540 reviews)
"Everything was clean, easy check in process and convenient location, walking distance to multiple restaurants."
United States
Bill
The price is €101
includes taxes & fees
9 Nov - 10 Nov
Trade Winds on the Bay

2. Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (236 reviews)
"Very nice and cozy stay and the hosts were very kind and helpful. Highly recommend!"
United States
Skand
The price is €185
includes taxes & fees
9 Nov - 10 Nov
Cozy Cabin By The Pond, Sleeps 2

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

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (41 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 €134
includes taxes & fees
6 Dec - 7 Dec
Simplicity-Just what you need! STR24-20

4. 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
Restful Maine Cabin 6 • Fire Pit • Sauna • Beach

5. 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 €339
includes taxes & fees
9 Nov - 10 Nov
Waterfront Getaway Near Acadia w/ Spectacular View

6. NEW Dreamy cabin overlooking Penobscot Bay

NEW Dreamy cabin overlooking Penobscot Bay
Stockton Springs
10.0 out of 10, Exceptional, (1 review)
"Just book it!!! This beautiful cabin is even better than in pictures! The property is so peaceful and a great place to explore Maine coastal area. We stopped on our way up to Bar Harbor, I wish we had time to stay longer! The cabin was brand new had beautiful hand crafted wooden elements. The inside was spotless with so many smart uses of space. The decor was something that stood out to me, it felt so posh and thoughtful with the interior design. We stayed with my teenage son- he approved and we...
United States
Dana B.
NEW Dreamy cabin overlooking Penobscot Bay

7. Cozy Cabin 3 • Forest Escape • Cedar Sauna + Firepit

Cozy Cabin 3 • Forest Escape • Cedar Sauna + Firepit
Stockton Springs
10.0 out of 10, Exceptional, (9 reviews)
"The cabin was cozy and clean, providing just what we needed for a comfortable stay. Our host was fantastic; I had an issue receiving his messages, but it was resolved during our visit. The location is convenient, just a 40-minute drive to and from Bangor Airport and a little over an hour's drive to Acadia National Park. I highly recommend this cabin."
United States
Shoko
Cozy Cabin 3 • Forest Escape • Cedar Sauna + Firepit

8. Cabin 1 Near Sandy Point Beach + Wood-Fired Sauna

Cabin 1 Near Sandy Point Beach + Wood-Fired Sauna
Stockton Springs
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful setting, great views. Clean cabin with a very comfortable bed. No kitchen, but brought the coleman stove and it worked perfectly! Definitely recommend."
United States
Karen C.
Cabin 1 Near Sandy Point Beach + Wood-Fired Sauna

9. Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna

Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna
Stockton Springs
10.0 out of 10, Exceptional, (10 reviews)
"Lovely little cabin in an ideal location. Would definitely stay there again."
United States
oliver w.
Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna

10. Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna

Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna
Stockton Springs
10.0 out of 10, Exceptional, (19 reviews)
"We enjoyed our time, the cabin is cute but super convient and perfect use of the space. "
Netherlands
Marten K.
Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna

11. Cabin 4 • Unwind in Nature • Beach • Cedar Sauna

Cabin 4 • Unwind in Nature • Beach • Cedar Sauna
Stockton Springs
10.0 out of 10, Exceptional, (5 reviews)
"Cabin small, very cozy had everything we needed, peace and quiet . Very clean!"
United States
Kathy P.
Cabin 4 • Unwind in Nature • Beach • Cedar Sauna

12. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
The price is €490
includes taxes & fees
9 Nov - 10 Nov
Fully Updated Airy Historic Home in West Rockport

13. NEW BUILD Midcoast cabin! Sauna & walk to beach

NEW BUILD Midcoast cabin! Sauna & walk to beach
Stockton Springs
NEW BUILD Midcoast cabin! Sauna & walk to beach

14. 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 €331
includes taxes & fees
9 Nov - 10 Nov
Lone Star Lodge - Newly Renovated Studio

15. Phoenix Nest - Downtown Apartment in Belfast

Phoenix Nest - Downtown Apartment in Belfast
Belfast
9.4 out of 10, Exceptional, (3 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 €319
includes taxes & fees
9 Nov - 10 Nov
Phoenix Nest - Downtown Apartment in Belfast

16. Harbor/🦞 Pound Access & Views from Large Deck

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (84 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
The price is €386
includes taxes & fees
6 Dec - 7 Dec
Harbor/🦞 Pound Access & Views from Large Deck

17. 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 €262
includes taxes & fees
9 Nov - 10 Nov
Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House

18. Apt 1 Studio apartment in downtown Stonington

Apt 1 Studio apartment in downtown Stonington
Stonington
9.8 out of 10, Exceptional, (87 reviews)
"Nice place. Very cozy"
United States
Mark
The price is €240
includes taxes & fees
13 Nov - 14 Nov
Apt 1 Studio apartment in downtown Stonington

19. Brand new farm cottage close to downtown Blue Hill and Acadia National Park

Brand new farm cottage close to downtown Blue Hill and Acadia National Park
Blue Hill
9.4 out of 10, Exceptional, (42 reviews)
"Quiet and relaxing location."
United States
Al L.
The price is €157
includes taxes & fees
9 Nov - 10 Nov
Brand new farm cottage close to downtown Blue Hill and Acadia National Park

20. Blue Hill in the Woods

Blue Hill in the Woods
Blue Hill
9.2 out of 10, Wonderful, (5 reviews)
"Super clean, very cute. Host was very responsive. Exactly as advertised."
United States
Abbey M.
The price is €198
includes taxes & fees
13 Nov - 14 Nov
Blue Hill in the Woods
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.

Find holiday rentals that suit your style

Top Islesboro Hotel Reviews

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, apart-hotels, 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 favorite 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 depends 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 €101 per night. Entering your travel dates in the search wizard you might find 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.

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