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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Islesboro

Island log home in Maine with ocean views

Islesboro
10.0 out of 10, Exceptional, (87)
"Another great stay at the cabin. We are already looking forward to next summer!"
United States
William P.
Island log home in Maine with ocean views

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

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

Lincolnville
8.0 out of 10, Very good, (11)
"We had the best nights' sleep of our lives in this rustic cabin! Super quiet and peaceful. Excellent star watching. Masha was so nice and extremely hospitable! "
United States
Allison
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

Point Lookout

3.0 star property
Lincolnville
9.8 out of 10, Exceptional, (12)
"The best place to relax! Love everything about it from the incredibly comfy bed, fully useable kitchen, cozy gas woodstove. Can' t wait to return!"
United States
Anne
Point Lookout

Gorgeous Waterfront Estate In Historic Bayside

Northport
10.0 out of 10, Exceptional, (76)
"This was a great place with great owners. Would recommend to anyone"
United States
John S.
Gorgeous Waterfront Estate In Historic Bayside

Cozy Cabin on Blue Hill Farm

Blue Hill
9.8 out of 10, Exceptional, (27)
"every thing was fine. enjoyed our stay thanks"
United States
joan m.
Cozy Cabin on Blue Hill Farm

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!

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 AU$281
includes taxes & fees
9 Dec - 10 Dec
Cozy Cabin By The Pond, Sleeps 2

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

Camden
9.0 out of 10, Wonderful, (79)
"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

Waterfront cottage with deep water dock, ocean front.

Belfast
9.8 out of 10, Exceptional, (107)
"Truly lovely cottage. Jon is a fantastic host. Highly recommend!"
United States
Peter F.
Waterfront cottage with deep water dock, ocean front.

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

Northport
9.6 out of 10, Exceptional, (55)
"Easy Check in. Large kitchen and two large refrigerators were great for our large family. "
United States
Nelson G.
PINE LODGE NORTHPORT MAINE FAMILY REUNIONS, WEDDING,RETREAT ACADIA BAR HARBOR

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 AU$505
includes taxes & fees
10 Dec - 11 Dec
Comfortable, Close to Town Home, with Oceanview.

Ocean-view penthouse with deck, gas grill, washer/dryer, full kitchen, & WiFi

Rockland
9.6 out of 10, Exceptional, (34)
"It was exactly as described, the owners were lovely and we had the best time. I would absolutely stay here again. The beds were super comfy!"
United States
Susannah A.
Ocean-view penthouse with deck, gas grill, washer/dryer, full kitchen, & WiFi

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

South Thomaston
9.2 out of 10, Wonderful, (21)
"House was lovely, clean and well appointed. The location couldn’t have been nicer. We loved it!"
United States
patricia h.
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range

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

Charming 3-bedroom house in delightful Belfast, Maine

Belfast
10.0 out of 10, Exceptional, (3)
"Fantastic spot. Well appointed and comfortable. "
United States
Ariel B.
The price is AU$689
includes taxes & fees
9 Dec - 10 Dec
Charming 3-bedroom house in delightful Belfast, Maine

Family Home in Rockport, ME, 5 minutes away from Camden, ME.

Rockport
9.6 out of 10, Exceptional, (42)
"Beautiful place. Very nice people "
United States
Kelly T.
Family Home in Rockport, ME, 5 minutes away from Camden, ME.

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

Camden
9.8 out of 10, Exceptional, (90)
"Very quiet place, great place to relax! "
United States
Gail C.
Morning sun, coffee in hand, a good book and so much more...

Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill

Winterport
10.0 out of 10, Exceptional, (3)
"Older home with charm and some nice updates. It was perfect for our family of 6 and our dog. Kids appreciated the private pool on the 95° days and the dog loved the river. Couch is super comfortable and the outside area let us spend time together. Acadia is just over an hour away and it was a great home away from home for us."
United States
kimberly p.
Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill

Secluded Orland Cottage w/ Grill, Near State Parks

3.0 star property
Orland
Secluded Orland Cottage w/ Grill, Near State Parks
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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$281 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 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.