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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Islesboro vacation rentals

Lobby sitting area

1. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (519 reviews)
"the views were incredible, staff friendly and accommodations comfortable."
United States
Allene
$96 nightly
The price is $105
Oct 30 - Oct 31
Total with taxes and fees
Trade Winds on the Bay
A coastal town with boats docked at a marina, surrounded by lush greenery and hills.

2. 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
Pine Grove Cottages
Exterior

3. Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (6 reviews)
"A wonderful place to stay close walking distance to downtown Rockport"
United States
Joshua H.
$225 nightly
The price is $245
Oct 21 - Oct 22
Total with taxes and fees
Romantic Coastal Escape near Harbor
A patio with a table and chairs, surrounded by a grassy lawn and a wooded area.

4. Country Charm: Cozy getaway in delightful Searsport

Country Charm: Cozy getaway in delightful Searsport
Searsport
9.4 out of 10, Exceptional, (29 reviews)
"Great place. Beautiful location. Clean and pet friendly"
United States
Tri C.
$156 nightly
The price is $170
Oct 30 - Oct 31
Total with taxes and fees
Country Charm: Cozy getaway in delightful Searsport
A serene lakeside setting with a wooden dock and a gazebo.

5. 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
$185 nightly
The price is $201
Nov 1 - Nov 2
Total with taxes and fees
Cozy Cabin By The Pond, Sleeps 2
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

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

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (37 reviews)
"This was such a super cute place. Great little get away. Very clean! I would definitely recommend this place if you are in the area!"
United States
Beth
$139 nightly
The price is $152
Oct 20 - Oct 21
Total with taxes and fees
Simplicity-Just what you need! STR24-20
A wooden cabin with a door and window, surrounded by dense forest.

7. 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
$238 nightly
The price is $259
Nov 4 - Nov 5
Total with taxes and fees
Restful Maine Cabin 6 • Fire Pit • Sauna • Beach
A modern building with a dark exterior, a wooden door, and a small porch area.

8. NEW Dreamy cabin overlooking Penobscot Bay

NEW Dreamy cabin overlooking Penobscot Bay
Stockton Springs
10.0 out of 10, Exceptional, (1 review)
"Just book it!!! This beautiful cabin is even better than in pictures! The property is so peaceful and a great place to explore Maine coastal area. We stopped on our way up to Bar Harbor, I wish we had time to stay longer! The cabin was brand new had beautiful hand crafted wooden elements. The inside was spotless with so many smart uses of space. The decor was something that stood out to me, it felt so posh and thoughtful with the interior design. We stayed with my teenage son- he approved and we...
United States
Dana B.
$296 nightly
The price is $322
Nov 2 - Nov 3
Total with taxes and fees
NEW Dreamy cabin overlooking Penobscot Bay
A cabin with a wooden exterior, surrounded by large rocks and trees.

9. 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.
$240 nightly
The price is $261
Oct 20 - Oct 21
Total with taxes and fees
Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna
A wooden deck with outdoor seating, a fire pit, and a view of a harbor with boats and buildings.

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.
$174 nightly
The price is $190
Oct 27 - Oct 28
Total with taxes and fees
J & E Riggins - Inn on the Harbor
A wooden dock leading to a beach with a picnic table and chairs, surrounded by greenery.

11. 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.
$374 nightly
The price is $408
Nov 1 - Nov 2
Total with taxes and fees
Waterfront Getaway Near Acadia w/ Spectacular View
A deck with a table and chairs, a potted plant, and a view of a lake.

12. Rustic luxury waterfront apartment, 2 decks, kayaks, fireplace, peace & beauty.

Rustic luxury waterfront apartment, 2 decks, kayaks, fireplace, peace & beauty.
Penobscot
10.0 out of 10, Exceptional, (1 review)
"None of us wanted to leave. The Roost will be our first choice whenever we return. Barb and Les made us feel right at home. We had deer and turkey visit the yard and the bird watching from the dock was excellent. I can't find a single thing to improve upon here. "
United States
Cindy C.
$383 nightly
The price is $417
Oct 21 - Oct 22
Total with taxes and fees
Rustic luxury waterfront apartment, 2 decks, kayaks, fireplace, peace & beauty.
A small cabin with a front porch and a covered deck area, surrounded by tall trees.

13. 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.
Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly
A cozy bedroom with a bed, a large window, and a view of the outdoors.

14. 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.
$351 nightly
The price is $383
Oct 20 - Oct 21
Total with taxes and fees
Lone Star Lodge - Newly Renovated Studio
A wooden cabin with two Adirondack chairs outside, surrounded by a forested area with a gravel path and rocks.

15. 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
$240 nightly
The price is $261
Oct 20 - Oct 21
Total with taxes and fees
Cozy Cabin 3 • Forest Escape • Cedar Sauna + Firepit
A wooden deck with wicker rocking chairs overlooking a lake.

16. 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, (9 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.
$377 nightly
The price is $411
Oct 25 - Oct 26
Total with taxes and fees
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
A cabin with two windows, a door, and two chairs outside.

17. 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.
$240 nightly
The price is $261
Oct 20 - Oct 21
Total with taxes and fees
Cabin 1 Near Sandy Point Beach + Wood-Fired Sauna
A cabin with a wooden exterior, surrounded by large rocks and trees.

18. 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.
$240 nightly
The price is $261
Oct 20 - Oct 21
Total with taxes and fees
Cabin 4 • Unwind in Nature • Beach • Cedar Sauna
A wooden cabin with a door and window, surrounded by dense forest.

19. 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.
$251 nightly
The price is $274
Nov 5 - Nov 6
Total with taxes and fees
Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna
A living room with a sofa, armchair, TV, bookshelf, and a window with blinds.

20. Phoenix Nest - Downtown Apartment in Belfast

Phoenix Nest - Downtown Apartment in Belfast
Belfast
9.0 out of 10, Wonderful, (2 reviews)
"I just felt like we were paying City prices for a small town really cute little town but whose I can say Manhattan for the same price"
United States
Tom K.
$334 nightly
The price is $364
Oct 20 - Oct 21
Total with taxes and fees
Phoenix Nest - Downtown Apartment in Belfast
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

Camp DeForest

Camp DeForest

10/10 Excellent
"Every little detail was so well thought out and clean. We loved our stay and wish we had a few more days to enjoy all the amenities. We'll be back!"
Kim 1-night trip
Posted 4 hours ago
Camp DeForest

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 $105 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.

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.