Islesboro Holiday Rentals from NZ$209: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Islesboro has to offer?

Island log home in Maine with ocean views : This highly rated holiday home rental in Islesboro offers a fireplace, a patio and a BBQ 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 holiday with amenities such as a garden.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Islesboro holiday rentals

1. Trade Winds on the Bay

Rockland

Allene

includes taxes & fees

22 Nov - 23 Nov

2. Romantic Coastal Escape near Harbor

Rockport

Joshua H.

includes taxes & fees

25 Oct - 26 Oct

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.

includes taxes & fees

30 Oct - 31 Oct

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

4. Cozy Cabin By The Pond, Sleeps 2

Waldo

Skand

includes taxes & fees

1 Nov - 2 Nov

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

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

Stockton Springs

Marissa

includes taxes & fees

29 Oct - 30 Oct

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

includes taxes & fees

26 Oct - 27 Oct

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

includes taxes & fees

26 Oct - 27 Oct

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.

includes taxes & fees

27 Oct - 28 Oct

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.

includes taxes & fees

2 Nov - 3 Nov

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.

includes taxes & fees

4 Nov - 5 Nov

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

includes taxes & fees

29 Oct - 30 Oct

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.

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

2 Nov - 3 Nov

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

Stockton Springs

Kathy P.

includes taxes & fees

4 Nov - 5 Nov

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.

includes taxes & fees

24 Oct - 25 Oct

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

includes taxes & fees

29 Oct - 30 Oct

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

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

Stockton Springs

includes taxes & fees

4 Nov - 5 Nov

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.

includes taxes & fees

26 Oct - 27 Oct

19. Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna

Stockton Springs

oliver w.

includes taxes & fees

4 Nov - 5 Nov

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.

includes taxes & fees

23 Oct - 24 Oct

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Top Islesboro Hotel Reviews

Ledges by the Bay

10/10 Excellent

"Top"

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

Everything you need to know about Islesboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Islesboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Islesboro holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Islesboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Islesboro holiday rentals we have selected for you start as low as NZ$209 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Islesboro rentals

At Expedia, we put the best Islesboro holiday 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 holiday.

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 holiday rental in Islesboro?

Yes, there are holiday rentals close to the most popular sights in Islesboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Islesboro has to offer?

Island log home in Maine with ocean views: This highly rated holiday home rental in Islesboro offers a fireplace, a patio and a BBQ 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 holiday with amenities such as a garden.

How many holiday rentals are there in Islesboro?

With 9 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Islesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islesboro. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for families.

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Check prices for these dates

Our top choices for Islesboro holiday 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 holiday rentals that suit your style

Top Islesboro Hotel Reviews

Ledges by the Bay

Whitehall

Camp DeForest

Harkness Brook Inn

Cedar Crest Inn

Yankee Clipper Motel

Fort Knox Park Inn

High Tide Inn

Island log home in Maine with ocean views

Find out more about Islesboro

Frequently asked questions

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