Islesboro Vacation Rentals from $89: 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.

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Our top choices for Islesboro vacation rentals

1. Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

Lincolnville

Becki C.

$142 nightly

Sep 21 - Sep 22

Total with taxes and fees

2. Trade Winds on the Bay

Rockland

Todd

$82 nightly

Oct 20 - Oct 21

Total with taxes and fees

3. Pine Grove Cottages

Lincolnville

clinch

$219 nightly

Sep 21 - Sep 22

Total with taxes and fees

4. Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly

Lincolnville

Jeanean W.

$239 nightly

Sep 21 - Sep 22

Total with taxes and fees

5. Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden

Lincolnville

Julie

$195 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

Stockton Springs

Marissa

$231 nightly

Sep 21 - Sep 22

Total with taxes and fees

7. Pine Grove Cottages: Cottage 11

Lincolnville

Jack S.

$287 nightly

Sep 21 - Sep 22

Total with taxes and fees

8. Romantic Coastal Escape near Harbor

Rockport

$239 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

Stockton Springs

Marten K.

$238 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Stockton Springs

Karen C.

$231 nightly

Sep 21 - Sep 22

Total with taxes and fees

11. Secluded Cottage Getaway with Kitchenette near Lincolnville, Maine

Lincolnville

$271 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Stockton Springs

Kathy P.

$238 nightly

Sep 21 - Sep 22

Total with taxes and fees

13. Country Charm: Cozy getaway in delightful Searsport

Searsport

Lillian

$172 nightly

Sep 23 - Sep 24

Total with taxes and fees

14. Cozy Cabin By The Pond, Sleeps 2

Waldo

Jesse

$211 nightly

Oct 18 - Oct 19

Total with taxes and fees

15. Rustic Retreat Across from Lake; Family Friendly!

Union

Sallie S.

$354 nightly

Sep 23 - Sep 24

Total with taxes and fees

16. Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna

Stockton Springs

Olivier P.

$231 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Stockton Springs

Shoko

$231 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Penobscot

Mike C.

$379 nightly

Sep 27 - Sep 28

Total with taxes and fees

19. 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.

$309 nightly

Sep 21 - Sep 22

Total with taxes and fees

20. Cozy Cottage with Private Patio & Modern Amenities near Camden, Maine

Lincolnville

$346 nightly

Sep 21 - Sep 22

Total with taxes and fees

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Top Islesboro Hotel Reviews

Colonial Gables Oceanfront Village

10/10 Excellent

"Very nice ocean view"

Whitehall

10/10 Excellent

"We enjoyed staying here. It truly is the quintessential New England inn. It reminds me of the fictional Columbia Inn in the movie White Christmas. It is a bit worn here and there but it sort of adds to the vibe. Very laid back, relaxed atmosphere. We had a quiet room on the backside of the 2nd floor, with a view of the trees. We liked that we could open the window for fresh air. The bathroom was tight but the room overall was spacious and very comfortable. We liked the common areas of the property…. The porch, patios, and indoor seating areas. The property has an interesting history, an eclectic decor, board games and puzzles for some down time, and is in a perfect location between the center of town and Mt. Battie, which is a must see. We found a lot to like about Whitehall and would stay here again."

The Country Inn at Camden Rockport

8/10 Good

"Private quiet cottage, very clean. Mattress a bit lumpy, and the couch was not the most comfortable, but we were out and about most of the time so bo big deal. Breakfast was great with homemade waffles, danish, fruit, yogurt, eggs, coffee, juice and cereal. Staff was exceedingly friendly and helpful!"

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.

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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 Perry's Nut House, 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.

Islesboro Vacation Rentals

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Check prices for these dates

Our top choices for Islesboro vacation rentals

1. Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

2. Trade Winds on the Bay

3. Pine Grove Cottages

4. Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly

5. Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden

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

7. Pine Grove Cottages: Cottage 11

8. Romantic Coastal Escape near Harbor

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

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

11. Secluded Cottage Getaway with Kitchenette near Lincolnville, Maine

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

13. Country Charm: Cozy getaway in delightful Searsport

14. Cozy Cabin By The Pond, Sleeps 2

15. Rustic Retreat Across from Lake; Family Friendly!

16. Beautiful Maine Cabin 5 • Wood Fired Cedar Sauna

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

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

19. NEW Dreamy cabin overlooking Penobscot Bay

20. Cozy Cottage with Private Patio & Modern Amenities near Camden, Maine

Find vacation rentals that suit your style

Top Islesboro Hotel Reviews

Colonial Gables Oceanfront Village

Find out more about Islesboro

Explore a world of travel with Expedia

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