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

Islesboro Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Islesboro vacation rentals

A coastal town with boats docked at a marina, surrounded by lush greenery and hills.

1. 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
$240 nightly
The price is $262
Sep 29 - Sep 30
Total with taxes and fees
Pine Grove Cottages

2. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (499 reviews)
"Its a place to stay."
United States
Todd
$82 nightly
The price is $89
Oct 20 - Oct 21
Total with taxes and fees
Trade Winds on the Bay
A small cabin with a front porch and a covered deck area, surrounded by tall trees.

3. 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, (12 reviews)
"Great owner and quick night stay. "
United States
Jeanean W.
$229 nightly
The price is $250
Sep 29 - Sep 30
Total with taxes and fees
Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly
A calm lake with boats docked at a pier, surrounded by trees and hills.

4. 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, (15 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
$210 nightly
The price is $229
Sep 30 - Oct 1
Total with taxes and fees
Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden
A pond surrounded by trees, with two wooden chairs facing the water.

5. 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.
$142 nightly
The price is $154
Sep 29 - Sep 30
Total with taxes and fees
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
A two-story house with a front porch, a chimney, and a garage.

6. Cozy cottage -Close to Downtown Camden!

Cozy cottage -Close to Downtown Camden!
Camden
9.6 out of 10, Exceptional, (30 reviews)
"This property was clean, the kitchen was well appointed, it was close to downtown and the beds were very comfortable. I would stay here again or reccomend it to others."
United States
Abby S.
$484 nightly
The price is $528
Oct 23 - Oct 24
Total with taxes and fees
Cozy cottage -Close to Downtown Camden!
A cozy cabin interior with a wooden ceiling, a television mounted on the wall, a dining area with a table and chairs, and a kitchen with wooden cabinets.

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.
$271 nightly
The price is $295
Sep 29 - Sep 30
Total with taxes and fees
Pine Grove Cottages: Cottage 11
A cozy kitchen with wooden cabinets, a dining area with a table set for two, and a living area with a sofa.

8. Charming Cottage Retreat with Private Deck and BBQ near Camden, Maine

Charming Cottage Retreat with Private Deck and BBQ near Camden, Maine
Lincolnville
$360 nightly
The price is $393
Sep 29 - Sep 30
Total with taxes and fees
Charming Cottage Retreat with Private Deck and BBQ near Camden, Maine
A small cabin with a porch, surrounded by trees.

9. Cozy Cottage with Private Deck near West Penobscot Bay, Maine

Cozy Cottage with Private Deck near West Penobscot Bay, Maine
Lincolnville
$247 nightly
The price is $269
Sep 29 - Sep 30
Total with taxes and fees
Cozy Cottage with Private Deck near West Penobscot Bay, Maine
A wooden deck with red Adirondack chairs overlooking a body of water with boats.

10. The Barnacle On Bucks Harbor

The Barnacle On Bucks Harbor
Brooksville
10.0 out of 10, Exceptional, (2 reviews)
"The Barnacle is an amazing spot on Buck's Harbor for a family gathering. "
United States
Bayard B.
The Barnacle On Bucks Harbor
A spacious kitchen with wooden cabinets, a dining area with a table and chairs, and a ceiling fan.

11. Unique Coastal Maine Flower Farm Stay

Unique Coastal Maine Flower Farm Stay
Belmont
9.4 out of 10, Exceptional, (21 reviews)
"Peaceful and pretty place to stay!"
United States
Sara G.
$378 nightly
The price is $412
Sep 29 - Sep 30
Total with taxes and fees
Unique Coastal Maine Flower Farm Stay
A patio with a table and chairs, surrounded by a grassy lawn and a wooded area.

12. Country Charm: Cozy getaway in delightful Searsport

Country Charm: Cozy getaway in delightful Searsport
Searsport
9.4 out of 10, Exceptional, (27 reviews)
"Nice deck with tiki torches. The sofa was in the kitchen area."
United States
Lillian
$245 nightly
The price is $267
Oct 6 - Oct 7
Total with taxes and fees
Country Charm: Cozy getaway in delightful Searsport
A wooden deck with wicker rocking chairs overlooking a lake.

13. 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.
$410 nightly
The price is $447
Oct 25 - Oct 26
Total with taxes and fees
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
A grassy yard with a small table and chairs, a house, and a lake in the background.

14. Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
8.0 out of 10, Very good, (3 reviews)
"The cottage is cute with a great view of the lake. Quiet and peaceful yet convenient to town. Plenty to see and do in the area. We had a wonderful time and I highly recommend staying here!"
United States
Lorraine
$346 nightly
The price is $377
Sep 29 - Sep 30
Total with taxes and fees
Rustic Retreat Across From Lake; Family Friendly!
A serene lakeside setting with a wooden dock and a gazebo.

15. Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (232 reviews)
"Amazing people, amazing property"
United States
Jesse
$205 nightly
The price is $223
Oct 18 - Oct 19
Total with taxes and fees
Cozy Cabin By The Pond, Sleeps 2
A covered porch with a grill, a potted plant, and a small table.

16. Cheerful Two Bedroom Cabin - 10 minutes to Camden!

Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
9.8 out of 10, Exceptional, (16 reviews)
"You can tell this from the photos, but the cabin is very well appointed with high quality touches throughout. Beds are very comfortable, and all linens, soaps, shampoos, etc. are lux level. Wonderful stay, and great communications with the owner."
United States
Tom M.
$489 nightly
The price is $533
Sep 29 - Sep 30
Total with taxes and fees
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
A cabin with a wooden exterior, surrounded by large rocks and trees.

17. 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.
$231 nightly
The price is $252
Sep 29 - Sep 30
Total with taxes and fees
Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna

18. 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.
$234 nightly
The price is $255
Oct 21 - Oct 22
Total with taxes and fees
Romantic Coastal Escape near Harbor
An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

19. Harbor/🦞 Pound Access & Views from Large Deck

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (82 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
$436 nightly
The price is $475
Oct 13 - Oct 14
Total with taxes and fees
Harbor/🦞 Pound Access & Views from Large Deck
A large, light-colored house with a garage, surrounded by lush greenery and a lake.

20. Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!

Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!
Penobscot
10.0 out of 10, Exceptional, (2 reviews)
"If you are looking for a true relaxing coastal Maine vacation this is the place for you. The property is so peaceful and Barb, Les and Miss Pepper are the most accomodating hosts. This property is as advertised and then some. We had a wonderful stay!!"
United States
Taasha A.
Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!
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

8/10 Good
"Nice quaint hotel, convenient location between 2 cute towns. Room was nice and liked the small deck to sit outside and parking right in front of the room. Only issue was a very small shower stall. The hotel had an enclosed outdoor porch area where the breakfast was served in the morning."
Crystal 3-night trip
Posted 8 hours ago
Glen Cove Inn & Suites

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 $89 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

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.