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Islesboro Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (537 reviews)
"Everything was clean, easy check in process and convenient location, walking distance to multiple restaurants."
United States
Bill
$109 nightly
The price is $119
Nov 5 - Nov 6
Total with taxes and fees
Trade Winds on the Bay
A small cabin with a porch, surrounded by lush greenery and a pond.

2. Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (235 reviews)
"Very nice and cozy stay and the hosts were very kind and helpful. Highly recommend!"
United States
Skand
$185 nightly
The price is $201
Nov 7 - Nov 8
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.

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

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (38 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
$124 nightly
The price is $135
Nov 5 - Nov 6
Total with taxes and fees
Simplicity-Just what you need! STR24-20
A wooden cabin with a door and window, surrounded by dense forest.

4. 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
$234 nightly
The price is $255
Nov 5 - Nov 6
Total with taxes and fees
Restful Maine Cabin 6 • Fire Pit • Sauna • Beach
A wooden dock leading to a beach with a picnic table and chairs, surrounded by greenery.

5. 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.
$351 nightly
The price is $382
Nov 8 - Nov 9
Total with taxes and fees
Waterfront Getaway Near Acadia w/ Spectacular View
A modern building with a dark exterior, a wooden door, and a small porch area.

6. 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.
$295 nightly
The price is $322
Nov 6 - Nov 7
Total with taxes and fees
NEW Dreamy cabin overlooking Penobscot Bay
A wooden cabin with two Adirondack chairs outside, surrounded by a forested area with a gravel path and rocks.

7. 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
$234 nightly
The price is $255
Nov 5 - Nov 6
Total with taxes and fees
Cozy Cabin 3 • Forest Escape • Cedar Sauna + Firepit
A cabin with two windows, a door, and two chairs outside.

8. 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.
$234 nightly
The price is $255
Nov 6 - Nov 7
Total with taxes and fees
Cabin 1 Near Sandy Point Beach + Wood-Fired Sauna
A wooden cabin with a door and window, surrounded by dense forest.

9. 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.
$234 nightly
The price is $255
Nov 5 - Nov 6
Total with taxes and fees
Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna
A cabin with a wooden exterior, surrounded by large rocks and trees.

10. 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.
$234 nightly
The price is $255
Nov 5 - Nov 6
Total with taxes and fees
Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna
A cabin with a wooden exterior, surrounded by large rocks and trees.

11. 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.
$234 nightly
The price is $255
Nov 5 - Nov 6
Total with taxes and fees
Cabin 4 • Unwind in Nature • Beach • Cedar Sauna
A living room with a sofa, a coffee table, a TV, a fireplace, and a window with curtains.

12. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
$508 nightly
The price is $554
Nov 6 - Nov 7
Total with taxes and fees
Fully Updated Airy Historic Home in West Rockport
A wooden deck with a glass door, two Adirondack chairs, and a bench.

13. NEW BUILD Midcoast cabin! Sauna & walk to beach

NEW BUILD Midcoast cabin! Sauna & walk to beach
Stockton Springs
$309 nightly
The price is $337
Nov 8 - Nov 9
Total with taxes and fees
NEW BUILD Midcoast cabin! Sauna & walk to beach
A bathroom with a white vanity, a mirror, and a shower curtain.

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.
$333 nightly
The price is $363
Nov 5 - Nov 6
Total with taxes and fees
Lone Star Lodge - Newly Renovated Studio
A living room with a sofa, armchair, TV, bookshelf, and a window with blinds.

15. 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.
$320 nightly
The price is $349
Nov 5 - Nov 6
Total with taxes and fees
Phoenix Nest - Downtown Apartment in Belfast
A wooden table and two chairs in a garden with a gravel path, surrounded by lush greenery and trees.

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

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (84 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
$379 nightly
The price is $413
Nov 5 - Nov 6
Total with taxes and fees
Harbor/🦞 Pound Access & Views from Large Deck
A wooden deck with two chairs and a view of a forested landscape.

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

Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House
Brooklin
9.8 out of 10, Exceptional, (6 reviews)
"The space was perfect for us. It was lovely and super convenient both for classes at WoodenBoat School and hikes at Acadia."
United States
Strephon T.
$262 nightly
The price is $285
Nov 5 - Nov 6
Total with taxes and fees
Cozy Little Carriage House with Spectacular Sunsets at The Rockbound House
A hotel room with a wooden paneled wall, a bed with a green bedspread, two white armchairs, a wooden nightstand with a lamp, and framed artwork on the wall.

18. Apt 1 Studio apartment in downtown Stonington

Apt 1 Studio apartment in downtown Stonington
Stonington
9.8 out of 10, Exceptional, (87 reviews)
"Nice place. Very cozy"
United States
Mark
$239 nightly
The price is $261
Nov 5 - Nov 6
Total with taxes and fees
Apt 1 Studio apartment in downtown Stonington
Blue Hill Downtown Fine Dining - Arborvine Restaurant

19. Brand new farm cottage close to downtown Blue Hill and Acadia National Park

Brand new farm cottage close to downtown Blue Hill and Acadia National Park
Blue Hill
9.4 out of 10, Exceptional, (42 reviews)
"Quiet and relaxing location."
United States
Al L.
$158 nightly
The price is $172
Nov 5 - Nov 6
Total with taxes and fees
Brand new farm cottage close to downtown Blue Hill and Acadia National Park
A compact kitchen with white cabinets, a black dishwasher, a coffee maker, and a microwave.

20. Blue Hill in the Woods

Blue Hill in the Woods
Blue Hill
9.2 out of 10, Wonderful, (5 reviews)
"Nice new apartment upstairs of the garage. It’s a spacious single room (except the bathroom of course), nicely laid out with pleasant lighting through windows looking out towards the trees. The “kitchen” is minimal: a dorm-sized fridge, microwave, toaster oven, water kettle and coffee maker. Sufficient for our needs but not enough for an extended stay. Given that the rental is a one-room studio with laminate flooring, the pet fee seemed a bit steep, but the apartment itself was a good bargain...
United States
Eric S.
$197 nightly
The price is $214
Nov 5 - Nov 6
Total with taxes and fees
Blue Hill in the Woods
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

An outdoor seating area with orange chairs and tables, surrounded by trees and string lights.
Camp DeForest

Camp DeForest

Camp DeForest
Lincolnville

10/10 Excellent

I live 24 hours away and I would travel all the way back for a weekend here. The detail that went into this place is incredible.
United States
Dondre
Reviewed November 2, 2026
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 $118 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.

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.

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