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Islesboro Vacation Rentals

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Dec 26 - Dec 28

Vacation Rentals in Islesboro

Island log home in Maine with ocean views
Fridge, microwave, oven, stovetop

Island log home in Maine with ocean views

10.0 out of 10, Exceptional, (82)
"Wonderful everything was clean and well furnished. Wil; book again "
Island log home in Maine with ocean views
Trade Winds on the Bay
Water view

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very Good, (280)
"The rooms were spacious and the view was beautiful!"
$101 nightly
The price is $111
Oct 14 - Oct 15
Total with taxes and fees
Trade Winds on the Bay
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Fridge, microwave, oven, stovetop

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
Property grounds

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

8.6 out of 10, Excellent, (8)
"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! "
$100 nightly
The price is $109
Oct 12 - Oct 13
Total with taxes and fees
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Pine Grove Cottages
Exterior

Pine Grove Cottages

2.5 star property
9.8 out of 10, Exceptional, (89)
"Wonderful quiet place, The Host was a great person."
$240 nightly
The price is $262
Oct 2 - Oct 3
Total with taxes and fees
Pine Grove Cottages
Point Lookout
Exterior

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
1812 Pierce House
Front of property

1812 Pierce House

3.5 star property
1812 Pierce House
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Marina

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

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...
Cozy Cabin on Blue Hill Farm
Interior

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

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

10.0 out of 10, Exceptional, (135)
"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.
House At The Point - Rustic Cottage on Ocean's Edge
Terrace/patio

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
Unique Coastal Maine Flower Farm Stay
Living area

Unique Coastal Maine Flower Farm Stay

9.6 out of 10, Exceptional, (15)
"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."
$384 nightly
The price is $419
Oct 2 - Oct 3
Total with taxes and fees
Unique Coastal Maine Flower Farm Stay
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
Exterior detail

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
Historic Cottage, Updated, short drive to town. 8 years of great reviews!
Exterior

Historic Cottage, Updated, short drive to town. 8 years of great reviews!

9.6 out of 10, Exceptional, (31)
"Great place. Everything's just as described. "
Historic Cottage, Updated, short drive to town. 8 years of great reviews!
Waterfront cottage with deep water dock, ocean front.
Exterior

Waterfront cottage with deep water dock, ocean front.

9.8 out of 10, Exceptional, (102)
"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.
Cozy Cabin By The Pond, Sleeps 2
Exterior

Cozy Cabin By The Pond, Sleeps 2

10.0 out of 10, Exceptional, (188)
"Cozy cabin was beautiful and had absolutely everything we needed for ourselves and our 2 dogs. They have truly thought of everything and work hard to make your stay the best it can be. Will definitely be booking again in the future. "
$185 nightly
The price is $201
Oct 12 - Oct 13
Total with taxes and fees
Cozy Cabin By The Pond, Sleeps 2
Beach Vacation - Private Balcony - Views
Interior

Beach Vacation - Private Balcony - Views

9.8 out of 10, Exceptional, (80)
"This was our 5th trip to Maine. We usually stay in Belfast but wanted something different this year. The place was perfect, clean and had everything that you would need. Love it!!!! Thank you for the tote bag it will definitely come in handy. Promise we will be back."
Beach Vacation - Private Balcony - Views
Rustic Searsport Cabin: Loft + Sunroom on 10 Acres
House (2 Bedrooms) | Interior

Rustic Searsport Cabin: Loft + Sunroom on 10 Acres

3.0 star property
10.0 out of 10, Exceptional, (3)
"This cabin is very well decorated with comfortable bedding and furniture. The decor and taxidermy are consistent with a rustic cabin, while the kitchen is set up well to cook, with all the condiments and seasonings to be able to eat in if you choose. The cabin and the nearby hosts both exceeded expectations."
Rustic Searsport Cabin: Loft + Sunroom on 10 Acres
35 Mi to Acadia: Rustic Retreat in Orland!
House (1 Bedroom) | Interior

35 Mi to Acadia: Rustic Retreat in Orland!

2.0 star property
10.0 out of 10, Exceptional, (1)
"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. "
35 Mi to Acadia: Rustic Retreat in Orland!
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

Glen Cove Inn & Suites

Glen Cove Inn & Suites

10/10 Excellent
"The girl that checked us in was very helpful. Very cozy little place. Clean and comfy. Breakfast was good and plentiful. "
Leonard 2-night trip
Posted 2 days ago
Glen Cove Inn & Suites

Find out more about Islesboro

Find out more about Islesboro

Everything you need to know about Islesboro vacation rentals

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

Islesboro vacation 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 low season months. For more hustle and bustle, you may prefer to visit Islesboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $109 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Islesboro rentals

At Expedia, we put the best Islesboro vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Islesboro?

Yes, you can find vacation rentals close to the most popular points of interest in Islesboro, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Islesboro has to offer?

1812 Pierce House: This vacation home rental outside of Islesboro is equipped with a barbecue grill, 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 vacation rentals are there in Islesboro?

With 9 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Islesboro like?

Vacation rentals are private properties where you can stay for short or long periods in Islesboro. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips.