Islesboro Vacation Rentals from ￥18,816: Search Short-Term Rentals

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Islesboro vacation rentals

1. Trade Winds on the Bay

Rockland

Allene

￥18,816 total

includes taxes & fees

Nov 22 - Nov 23

2. Romantic Coastal Escape near Harbor

Rockport

Joshua H.

￥39,163 total

includes taxes & fees

Oct 25 - Oct 26

A patio with a table and chairs, surrounded by a grassy lawn and a wooded area.

3. Country Charm: Cozy getaway in delightful Searsport

Searsport

Tri C.

￥26,906 total

includes taxes & fees

Oct 30 - Oct 31

A small cabin with a porch, surrounded by lush greenery and a pond.

4. Cozy Cabin By The Pond, Sleeps 2

Waldo

Skand

￥31,810 total

includes taxes & fees

Nov 2 - Nov 3

A wooden cabin with a door and window, surrounded by dense forest.

5. Restful Maine Cabin 6 • Fire Pit • Sauna • Beach

Stockton Springs

Marissa

￥41,026 total

includes taxes & fees

Oct 29 - Oct 30

A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

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

Rockland

Beth

￥24,016 total

includes taxes & fees

Oct 26 - Oct 27

A living room with a sofa, a coffee table, a TV, a fireplace, and a window with curtains.

7. Fully Updated Airy Historic Home in West Rockport

Rockport

￥93,163 total

includes taxes & fees

Oct 26 - Oct 27

A wooden deck with outdoor seating, a fire pit, and a view of a harbor with boats and buildings.

8. J & E Riggins - Inn on the Harbor

Stonington

Thomas K.

￥26,818 total

includes taxes & fees

Oct 27 - Oct 28

A modern building with a dark exterior, a wooden door, and a small porch area.

9. NEW Dreamy cabin overlooking Penobscot Bay

Stockton Springs

"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...

Dana B.

￥51,032 total

includes taxes & fees

Nov 4 - Nov 5

A wooden dock leading to a beach with a picnic table and chairs, surrounded by greenery.

10. Waterfront Getaway Near Acadia w/ Spectacular View

Deer Isle

Thomas P.

￥63,404 total

includes taxes & fees

Nov 4 - Nov 5

A wooden cabin with two Adirondack chairs outside, surrounded by a forested area with a gravel path and rocks.

11. Cozy Cabin 3 • Forest Escape • Cedar Sauna + Firepit

Stockton Springs

Shoko

￥40,998 total

includes taxes & fees

Nov 1 - Nov 2

A cabin with two windows, a door, and two chairs outside.

12. Cabin 1 Near Sandy Point Beach + Wood-Fired Sauna

Stockton Springs

Karen C.

￥41,026 total

includes taxes & fees

Nov 4 - Nov 5

A cabin with a wooden exterior, surrounded by large rocks and trees.

13. Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna

Stockton Springs

Marten K.

￥41,026 total

includes taxes & fees

Nov 1 - Nov 2

14. Cabin 4 • Unwind in Nature • Beach • Cedar Sauna

Stockton Springs

Kathy P.

￥41,026 total

includes taxes & fees

Nov 4 - Nov 5

A wooden deck with two chairs and a view of a forested landscape.

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

Brooklin

Strephon T.

￥45,659 total

includes taxes & fees

Oct 24 - Oct 25

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.

16. Apt 1 Studio apartment in downtown Stonington

Stonington

Mark

￥41,895 total

includes taxes & fees

Oct 26 - Oct 27

A wooden deck with a glass door, two Adirondack chairs, and a bench.

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

Stockton Springs

￥52,378 total

includes taxes & fees

Nov 4 - Nov 5

A wooden deck with wicker rocking chairs overlooking a lake.

18. SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature

Penobscot

Mike C.

￥65,595 total

includes taxes & fees

Oct 26 - Oct 27

19. Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna

Stockton Springs

oliver w.

￥43,441 total

includes taxes & fees

Nov 4 - Nov 5

A cozy bedroom with a bed, a large window, and a view of the outdoors.

20. Lone Star Lodge - Newly Renovated Studio

Northport

Evelyn F.

￥60,169 total

includes taxes & fees

Nov 2 - Nov 3

View all properties

Find vacation rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Islesboro Hotel Reviews

Whitehall

8/10 Good

"Smell very good"

Harkness Brook Inn

10/10 Excellent

"We had a very pleasant stay at this hotel! The area was peaceful and quiet, which made it a great place to relax. The hotel itself was beautiful, well-maintained, and nicely renovated. Everything looked fresh and inviting, and the overall atmosphere was very cozy. The bed was very comfortable, although it did squeak quite a bit whenever we moved. Other than that, we had a great experience and really enjoyed the cozy feel of the place. Overall, it’s a lovely hotel in a quiet area, and I would definitely consider staying here again!"

Yankee Clipper Motel

8/10 Good

"The room was clean, well maintained, and attractively decorated. The room was a bit small. Staff I encountered were pleasant and helpful, but the office is not staffed until afternoon, so we had no interaction other than when checking in. This motel provided comfortable beds and pillows. On a busy road but I really didn’t hear road noise from the room or noise from other patrons. Basic in its services, in that it didn’t provide breakfast, have a pool or onsite restaurant. Ice machine and washer/dryer available in room near office. That was appreciated. Towels were clean and replenished upon request, but are probably ready to be replaced. Enough mirrors/ good, but could use some wall hooks near door for jackets. Also more hooks in bathroom. Little counter space in bathroom, but shower had good pressure and easy to adjust heat."

High Tide Inn

10/10 Excellent

"The view was totally outstanding. The staff was amazing. Very informative, extremely friendly great suggestions for both what to do and restaurants. We definitely recommend all my friends and family to go there. Mark and Holly are the ultimate hosts. Mark is a wealth of knowledge and we enjoyed all of his stories and how he became a cook."

Find out more about Islesboro

Search for holiday rentals in Islesboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Islesboro using one of the methods below:

View our selection of featured holiday rentals in Islesboro
Use the map to find apartments and other holiday homes in the Islesboro neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Islesboro while they last

Look no further and take a look at our great range of rental properties in Islesboro!

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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Islesboro vacation rentals

1. Trade Winds on the Bay

2. Romantic Coastal Escape near Harbor

3. Country Charm: Cozy getaway in delightful Searsport

4. Cozy Cabin By The Pond, Sleeps 2

5. Restful Maine Cabin 6 • Fire Pit • Sauna • Beach

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

7. Fully Updated Airy Historic Home in West Rockport

8. J & E Riggins - Inn on the Harbor

9. NEW Dreamy cabin overlooking Penobscot Bay

10. Waterfront Getaway Near Acadia w/ Spectacular View

11. Cozy Cabin 3 • Forest Escape • Cedar Sauna + Firepit

12. Cabin 1 Near Sandy Point Beach + Wood-Fired Sauna

13. Quiet Maine Cabin 2 • Hideaway in the Trees • Sauna

14. Cabin 4 • Unwind in Nature • Beach • Cedar Sauna

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

16. Apt 1 Studio apartment in downtown Stonington

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

18. SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature

19. Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna

20. Lone Star Lodge - Newly Renovated Studio

Find vacation rentals that suit your style

Top Islesboro Hotel Reviews

Whitehall

Camp DeForest

Rockland Harbor Hotel

Harkness Brook Inn

Cedar Crest Inn

Yankee Clipper Motel

Ledges by the Bay

Fort Knox Park Inn

High Tide Inn

Find out more about Islesboro

Frequently asked questions

Go further with the Expedia app