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

Islesboro Vacation Rentals

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Our top choices for Islesboro vacation rentals

1. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (515 reviews)
"the views were incredible, staff friendly and accommodations comfortable."
United States
Allene
The price is CA $123
CA $134 total
includes taxes & fees
Oct 20 - Oct 21
Trade Winds on the Bay

2. 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.
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

3. Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (6 reviews)
"My family of four greatly enjoyed our stay at this property. Location was very convenient to explore the mid coast towns of Rockport, Rockland, and Camden and all of their beautiful harbors. Having two bedrooms worked well for us along with the living room and a large open kitchen and full bathroom. The private entrance that leads up to the open top floor was easy to manage and appreciated. The quiet street was frequented by wild turkeys that roamed the yard and crossed the street on two...
United States
Christopher H.
The price is CA $173
CA $347 total
includes taxes & fees
Oct 21 - Oct 22
Romantic Coastal Escape near Harbor

4. Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (234 reviews)
"This was my favorite place to stay. Like having a little home of our own in Maine. Close to all the places we wanted to see."
United States
Janeen
The price is CA $173
CA $286 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Cabin By The Pond, Sleeps 2

5. Pine Grove Cottages

Pine Grove Cottages
2.5 star property
Lincolnville
9.8 out of 10, Exceptional, (93 reviews)
"Wonderful quiet place, The Host was a great person."
United States
clinch
The price is CA $325
CA $372 total
includes taxes & fees
Oct 18 - Oct 19
Pine Grove Cottages

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, (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
The price is CA $186
CA $370 total
includes taxes & fees
Nov 4 - Nov 5
Restful Maine Cabin 6 • Fire Pit • Sauna • Beach

7. New build! Beach cabin in the trees & onsite sauna

New build! Beach cabin in the trees & onsite sauna
Stockton Springs
10.0 out of 10, Exceptional, (2 reviews)
"This was a great place and location. It was easy to find and would definitely come back!"
United States
Tom A.
The price is CA $220
CA $496 total
includes taxes & fees
Nov 8 - Nov 9
New build! Beach cabin in the trees & onsite sauna

8. 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 CA $186
CA $370 total
includes taxes & fees
Nov 4 - Nov 5
Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna

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

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (36 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is CA $138
CA $216 total
includes taxes & fees
Oct 18 - Oct 19
Simplicity-Just what you need! STR24-20

10. J & E Riggins - Inn on the Harbor

J & E Riggins - Inn on the Harbor
Stonington
10.0 out of 10, Exceptional, (11 reviews)
"Fab place!"
United States
Thomas K.
The price is CA $170
CA $283 total
includes taxes & fees
Oct 27 - Oct 28
J & E Riggins - Inn on the Harbor

11. 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.
The price is CA $205
CA $397 total
includes taxes & fees
Nov 8 - Nov 9
Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna

12. 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 CA $186
CA $373 total
includes taxes & fees
Nov 8 - Nov 9
Cabin 1 Near Sandy Point Beach + Wood-Fired Sauna

13. 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 CA $232
CA $598 total
includes taxes & fees
Oct 30 - Oct 31
Waterfront Getaway Near Acadia w/ Spectacular View

14. 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 CA $186
CA $370 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Cabin 3 • Forest Escape • Cedar Sauna + Firepit

15. 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.
The price is CA $186
CA $373 total
includes taxes & fees
Nov 8 - Nov 9
Cabin 4 • Unwind in Nature • Beach • Cedar Sauna

16. Apt 1 Studio apartment in downtown Stonington

Apt 1 Studio apartment in downtown Stonington
Stonington
9.8 out of 10, Exceptional, (85 reviews)
"Nice place. Very cozy"
United States
Mark
The price is CA $192
CA $381 total
includes taxes & fees
Oct 16 - Oct 17
Apt 1 Studio apartment in downtown Stonington

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

Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden
Lincolnville
9.8 out of 10, Exceptional, (17 reviews)
"Quant and cozy little cottage out in the peaceful quiet wooded area. Loved this place. Plenty of towels, washer and dryer, plenty of kitchen items. Will definitely stay again when in the area."
United States
Ruthanne
Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden

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

Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House
Brooklin
9.6 out of 10, Exceptional, (4 reviews)
"I had a good night's sleep"
United States
Robert H.
The price is CA $204
CA $430 total
includes taxes & fees
Oct 22 - Oct 23
Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House

19. Pine Grove Cottages: Cottage 3: Studio Cottage - Pet Friendly

Pine Grove Cottages: Cottage 3: Studio Cottage - Pet Friendly
Lincolnville
9.6 out of 10, Exceptional, (5 reviews)
"Incredibly clean cabin! The hosts were very helpful with suggestions on places to eat with our dog. Would definitely go back. "
United States
Sara
The price is CA $327
CA $408 total
includes taxes & fees
Oct 17 - Oct 18
Pine Grove Cottages: Cottage 3: Studio Cottage - Pet Friendly

20. 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 CA $319
CA $547 total
includes taxes & fees
Oct 20 - Oct 21
Lone Star Lodge - Newly Renovated Studio
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Islesboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Island log home in Maine with ocean views: This highly rated vacation home rental in Islesboro offers a fireplace, a patio, and a barbecue grill 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 vacation with amenities like a garden.

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 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 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.