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

Islesboro Holiday Rentals

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Our top choices for Islesboro holiday rentals

1. 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, (17 reviews)
"The cabin is exactly as advertised. The dogs were happy there and we enjoyed our stay. "
United States
Becki C.
The price is NZ$262
includes taxes & fees
7 Sept - 8 Sept
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

2. Pine Grove Cottages

Pine Grove Cottages
2.5 star property
Lincolnville
9.8 out of 10, Exceptional, (90 reviews)
"Wonderful quiet place, The Host was a great person."
United States
clinch
The price is NZ$467
includes taxes & fees
9 Sept - 10 Sept
Pine Grove Cottages

3. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (473 reviews)
"Great stay, great location."
United States
Jerold
The price is NZ$254
includes taxes & fees
7 Sept - 8 Sept
Trade Winds on the Bay

4. Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly

Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly
Lincolnville
10.0 out of 10, Exceptional, (11 reviews)
"Great owner and quick night stay. "
United States
Jeanean W.
The price is NZ$487
includes taxes & fees
8 Sept - 9 Sept
Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly

5. Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden

Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden
Lincolnville
9.6 out of 10, Exceptional, (13 reviews)
"This is an amazing little cabin in the woods! Kate is a great host and I highly recommend staying here if you are in the area. Lovely spot and if Lola the local pup is around to great you even better!"
United States
Julie
The price is NZ$417
includes taxes & fees
9 Sept - 10 Sept
Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden

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

Restful Maine Cabin 6 • Fire Pit • Sauna • Beach
Stockton Springs
10.0 out of 10, Exceptional, (11 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 NZ$409
includes taxes & fees
9 Sept - 10 Sept
Restful Maine Cabin 6 • Fire Pit • Sauna • Beach

7. Pine Grove Cottages: Cottage 11

Pine Grove Cottages: Cottage 11
Lincolnville
10.0 out of 10, Exceptional, (1 review)
"Great stay! Cabin was clean and very comfortable, would definitely recommend!!"
United States
Jack S.
The price is NZ$521
includes taxes & fees
8 Sept - 9 Sept
Pine Grove Cottages: Cottage 11

8. Cozy Cottage with Private Patio & Modern Amenities near Camden, Maine

Cozy Cottage with Private Patio & Modern Amenities near Camden, Maine
Lincolnville
The price is NZ$611
includes taxes & fees
8 Sept - 9 Sept
Cozy Cottage with Private Patio & Modern Amenities near Camden, Maine

9. Romantic Cottage Retreat for Couples near Lincolnville, Maine

Romantic Cottage Retreat for Couples near Lincolnville, Maine
Lincolnville
The price is NZ$559
includes taxes & fees
8 Sept - 9 Sept
Romantic Cottage Retreat for Couples near Lincolnville, Maine

10. 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.
The price is NZ$556
includes taxes & fees
28 Sept - 29 Sept
NEW Dreamy cabin overlooking Penobscot Bay

11. Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (4 reviews)
"The home is clean and very well stocked with anything you might need. Ty reached out to me to make sure everything was good and offered to bring anything I might need while staying there. Property is very well kept. I love the neighbors too. Bed was comfortable. We will be back next year."
United States
Sheila D.
The price is NZ$476
includes taxes & fees
5 Oct - 6 Oct
Romantic Coastal Escape near Harbor

12. Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (226 reviews)
"Amazing people, amazing property"
United States
Jesse
The price is NZ$389
includes taxes & fees
8 Sept - 9 Sept
Cozy Cabin By The Pond, Sleeps 2

13. 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.
The price is NZ$409
includes taxes & fees
7 Sept - 8 Sept
Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna

14. 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)
"Perfect for anybody passing by. This cozy setting as everything you need."
Canada
Olivier P.
The price is NZ$433
includes taxes & fees
9 Sept - 10 Sept
Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna

15. 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, (8 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.
The price is NZ$810
includes taxes & fees
27 Sept - 28 Sept
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature

16. 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.
The price is NZ$420
includes taxes & fees
8 Sept - 9 Sept
Cabin 1 Near Sandy Point Beach + Wood-Fired Sauna

17. 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
The price is NZ$431
includes taxes & fees
9 Sept - 10 Sept
Cozy Cabin 3 • Forest Escape • Cedar Sauna + Firepit

18. Country Charm: Cozy getaway in delightful Searsport

Country Charm: Cozy getaway in delightful Searsport
Searsport
9.4 out of 10, Exceptional, (25 reviews)
"Lovely spot, thoughtfully equipped — we had a wonderful, restful stay. Highly recommended!"
United States
Jerry K.
The price is NZ$319
includes taxes & fees
8 Sept - 9 Sept
Country Charm: Cozy getaway in delightful Searsport

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

Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House
Brooklin
10.0 out of 10, Exceptional, (2 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 NZ$523
includes taxes & fees
7 Sept - 8 Sept
Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House

20. Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
10.0 out of 10, Exceptional, (26 reviews)
"Great location with everything we needed."
United States
Thomas P.
The price is NZ$826
includes taxes & fees
16 Sept - 17 Sept
Waterfront Getaway Near Acadia w/ Spectacular View
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

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 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 NZ$254 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 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 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.