Photo by Colleen Johnson

Holiday Rentals in Islesboro

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Islesboro

Island log home in Maine with ocean views

10.0 out of 10, Exceptional, (80)
"This property owner was very accommodating and quick to respond. It was a beautiful spot."
Island log home in Maine with ocean views

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very good, (271)
"The Tradewinds on bay,quiet local rest and relax...."
Trade Winds on the Bay

Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

2.0 star property
8.8 out of 10, Excellent, (11)
"The home is on a beautiful, private piece of land right on the St. George River estuary. The views are absolutely stunning and there is a short path right to the water and rocks. It was a perfect spot for two couples to relax and convenient to explore the midcoast region."
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

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

8.0 out of 10, Very good, (5)
"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! "
The price is €97
includes taxes & fees
22 Oct - 23 Oct
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

House At The Point - Rustic Cottage on Ocean's Edge

9.8 out of 10, Exceptional, (17)
"We had the most amazing time at this little cabin. Great trips are made by their location and this cabin has the most incredible location. We will definitely stay here again! "
House At The Point - Rustic Cottage on Ocean's Edge

Pine Grove Cottages

2.5 star property
9.8 out of 10, Exceptional, (89)
"Wonderful quiet place, The Host was a great person."
The price is €223
includes taxes & fees
23 Sept - 24 Sept
Pine Grove Cottages

1812 Pierce House

3.5 star property
1812 Pierce House

Cozy Cabin on Blue Hill Farm

9.8 out of 10, Exceptional, (24)
"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! "
Cozy Cabin on Blue Hill Farm

Point Lookout

3.0 star property
9.6 out of 10, Exceptional, (9)
"Great location. Away from the down town bustle, but close enough to enjoy the best of both worlds. Clean cabin, great amenities. "
Point Lookout

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

9.8 out of 10, Exceptional, (84)
"It was so pleasant and relaxing. Close to the city and harbor "
Morning sun, coffee in hand, a good book and so much more...

WATERFRONT Maine Historical Cottage with Separate Guest Cottage

8.6 out of 10, Excellent, (8)
"loved staying here, such a charming spot. "
WATERFRONT Maine Historical Cottage with Separate Guest Cottage

Comfortable, Close to Town Home, with Oceanview.

9.6 out of 10, Exceptional, (81)
"We had a great stay while in town for a family event. We were ecstatic to be able to take our family dog with us on the trip. The view from the back deck was incredible and close to many local parks for hiking."
The price is €343
includes taxes & fees
7 Oct - 8 Oct
Comfortable, Close to Town Home, with Oceanview.

Unique Coastal Maine Flower Farm Stay

9.6 out of 10, Exceptional, (14)
"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."
The price is €366
includes taxes & fees
23 Sept - 24 Sept
Unique Coastal Maine Flower Farm Stay

Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

10.0 out of 10, Exceptional, (133)
"We loved this place! It was beautiful and in a convenient location. We highly recommend it."
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

Waterfront cottage with deep water dock, ocean front.

10.0 out of 10, Exceptional, (101)
"Beautiful swing and convenient to town. Live the stay even though the weather was less than cooperative."
Waterfront cottage with deep water dock, ocean front.

Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland

9.6 out of 10, Exceptional, (90)
"We enjoyed our stay very much. The view was perfect and we really enjoyed sitting on the porch."
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland

Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

10.0 out of 10, Exceptional, (125)
"Awesome place to stay .Close to so many great things to see and do. Highly recommended. "
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Fish Tale Cabin at Toddy Pond - water fun, close coastal towns/parks and more!

9.0 out of 10, Wonderful, (4)
"Most of the times, access to the peir were closed by the front cottage guest. The host need mark the common area for the enjoyment of all the guests. Otherwise, this a nice place to stay."
Fish Tale Cabin at Toddy Pond - water fun, close coastal towns/parks and more!

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

9.8 out of 10, Exceptional, (68)
"Beautiful and very cozy stay close to everything you’d want to do, hike, explore, enjoy. Whirlpool jets in the tub was great after a long hike and we loved stargazing on the terrace. "
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway

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

9.0 out of 10, Wonderful, (74)
"We had a great stay! The property was clean and exactly as described. Great location. The owners were very responsive ."
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
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

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 €97 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?

1812 Pierce House: This holiday home rental outside of Islesboro is equipped with a BBQ, air conditioning and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.