Holiday houses in Islesboro

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Top-rated holiday rentals in Islesboro

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Top Guest favourite
A charming cottage is framed by lush green trees, showcasing its light yellow exterior and welcoming front door. The grassy area surrounding the home offers a tranquil setting, and the clear sky above adds to the serene ambiance.
Guesthouse in Islesboro
4.96 out of 5 average rating, 48 reviews

Milk House

nice little cottage in Dark Harbor, near to everything. queen bed, so sleeps up to two in a quiet location for short or medium term stays. most reasonable amenities provided; hiking or social recommendations are available on request. (Wi-Fi speed excellent, though I was not able to use AirB&B's official Wi-Fi measurement option.) *Please be aware, we are on an island, which must be accessed by boat or ferry, so service can be interrupted. there's a gym at the Community Center, $10/day pass.

Guest favourite
A spacious sleeping area features a king-sized bed adorned with patterned bedding and accent pillows. Natural wood beams and a warm wood ceiling create an inviting atmosphere. Sunlight enters through a large window, illuminating a comfortable corner chair and a small side table.
Apartment in Northport
4.95 out of 5 average rating, 113 reviews

Off-Grid Oasis with Ocean Views, Near Rt. 1

Take in the ocean views from our quiet hilltop just 20 minutes from downtown Camden and 10 minutes from Belfast. This newly constructed above garage studio apartment is private, full of light, and effortlessly off-grid. The studio features a king-sized bed, table and chairs, comfy chair and bean bag, as well as a full bath. The patio area gives breathtaking views of the bay and island. A perfect oasis amid sight seeing! We also offer $20 back for multi-night stays. Please message for details.

Top Guest favourite
A fire pit surrounded by four chairs is positioned by the tranquil waters of Molasses Pond. The scene is framed by a grove of trees, with a dramatic sky stretching overhead, reflecting the calmness of the lake.
Home in Eastbrook
4.99 out of 5 average rating, 152 reviews

The Maine Getaway - Lakefront with Beach

If you are looking for a place to get away and relax, our house on Molasses Pond may be a good fit for you/your family. It is a hidden gem down a dirt road away from hustle and bustle. Peace and quiet is what you’ll find, along with a gorgeous view. It’s a great place for swimming, kayaking, paddle boarding, grilling, fishing, and laying on the hammock. We try to provide you with all the necessities you may need and are happy to answer any questions. We hope you enjoy it as much as we do!

Top Guest favourite
A charming two-story building features warm wood siding and a green metal roof. The entrance is framed by a covered porch and surrounded by well-maintained landscaping. Tall trees provide shade in the foreground, enhancing the welcoming appearance of the property.
Apartment in Washington
4.97 out of 5 average rating, 131 reviews

The Washington Suite on u-pick blueberry farm.

This unique place has a style all its own. No, he didn’t sleep here, Washington that is, but now you can. Our one-hundred-acre farm is located in the small rural village of Washington. It is located just 2/10 of a mile from the village center where the general store, library and town offices are located. Easy commute east to the coast and the must-see towns of Rockland, Rockport and Camden or west to our capitol, Augusta. One hour and forty minutes to Bar Harbor and Acadia national park.

Top Guest favourite
The cottage's exterior showcases charming architectural features, including a circular window and a cupola. A spacious deck is visible, surrounded by lush greenery and outdoor seating. The serene water views are framed by trees, enhancing the peaceful atmosphere of the Maine coastline.
Cottage in Northport
5 out of 5 average rating, 29 reviews

"Eagles Nest" Waterfront Cottage

Escape to our delightful waterfront cottage nestled along the rugged and breathtakingly beautiful coast of Maine. This charming and cozy retreat offers expansive water views and serene surroundings - ensuring the perfect blend of comfort and tranquility. Take in the fresh salty air, the soothing sounds of waves lapping the shore, and create lasting memories to cherish in this memorable seaside sanctuary. Book your stay with us and experience the enchanting beauty of Penobscot Bay.

Top Guest favourite
A wooden deck elevates the camp structure, featuring a railing with vertical slats. Two barstools are positioned along the edge, allowing for a view of the surrounding greenery. The structure's warm-toned wood complements the natural setting, with trees and sunlight visible in the background.
Tiny home in Blue Hill
4.94 out of 5 average rating, 288 reviews

New enchanting retreat near Acadia National

The camp is brand new on 27 acres of land 3 min to Blue Hill Mountain and 5 min to Blue Hill downtown which is right on the water of The Blue Hill Bay. This is an edge wood enchanting retreat perfect for two to hear birds, squirrels and porcupines. Remember to pick some blueberries when it is in season before the black baby bear down the road eat them all. 3D nature is unfolding right in front of your eyes and Acadia National Park is 50 min drive from here. Oh man, you are free! 编辑

Guest favourite
A cozy studio apartment features a wood-paneled interior with a spacious seating area, including a vibrant red sofa adorned with patterned cushions. A kitchen with green accents and white appliances is visible, along with a dining table and large windows allowing natural light to brighten the space.
Guesthouse in Lincolnville
4.93 out of 5 average rating, 150 reviews

Ocean View Beach Loft Carriage House Lincolnville

This charming spot overlooking the bay is laid back and welcoming. Fully furnished, including linens, basic beach supplies —towels, chairs and umbrella. There is wi-fi and a Roku TV included (you will need your own streaming accounts), an air conditioner, and balcony with a view of Penobscot Bay. We strive to be an allergen free space so do not allow animals. We use all essential oil natural products (bleach disinfectant where needed) and natural laundry soap for our linens.

Top Guest favourite
A scenic view is offered from a wooden deck, overlooking a lush green yard leading to a tranquil pond. Two planters with vibrant flowers and small American flags are positioned on the railing. Comfortable chairs are visible near the water under the trees.
Cottage in Penobscot
4.93 out of 5 average rating, 72 reviews

Charming Private Cottage on Toddy Pond

Beautiful Toddy Pond cottage, just minutes to Blue Hill and coastal surrounding towns. Less than an hour's drive to Acadia National Park. Enjoy the day lounging on the deck, boating, and swimming off the dock. Enjoy the evening by the fire pit under the starlit sky and listening to the Loons. The downstairs you will find living room, kitchen/dinning, full bath and washer/dryer. Upstairs is a one room bedroom with queen bed. Two kayaks provided. Perfect getaway for two!

Top Guest favourite
A contemporary yurt is nestled among snow-dusted trees, surrounded by a blanket of white snow. A spacious deck extends from the yurt, providing access to the inviting living space. The serene winter landscape and trees enhance the retreat's secluded charm.
Yurt in Appleton
4.95 out of 5 average rating, 356 reviews

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Guest favourite
A geodesic dome is prominently situated on an elevated deck, surrounded by vibrant fall foliage. The structure showcases a wooden finish, and a small detached building is visible nearby. Clear blue skies add to the serene outdoor setting, providing a peaceful ambiance.
Dome in Ellsworth
4.98 out of 5 average rating, 218 reviews

Nomad's Rest-Secluded Modern Camp 30 miles to MDI

The modern Maine camping experience. Enjoy an unforgettable stay in a geodesic dome outfitted with detached bathroom and shower. A fantastic jumping-off point for your favorite outdoor sports with hiking and biking trails within 10 minutes of the property and 30 miles from Acadia National Park. Return from a day of exploration to views of Maine lakes, the national park and a roaring fire pit! @nomaddomehome on Insta for more pictures.

Top Guest favourite
A rustic cabin is nestled among vibrant autumn foliage, showcasing a wooden exterior and green roof. A staircase leads up to the entrance, while a deck extends above, offering views of the surrounding forest. A stacked firewood pile is visible in the foreground.
Cabin in Lamoine
4.99 out of 5 average rating, 196 reviews

The Perch - cozy cabin near Acadia

Our unique and rustic post & beam cabin sits up a staircase atop a ledge on seven forested acres. The small cabin makes great use of space with modern-day conveniences. A private retreat (no neighbors in sight) yet close to Bar Harbor, Acadia National Park, and Schoodic Peninsula.

Top Guest favourite
The boathouse exterior features a two-story structure with a wraparound deck overlooking the harbor. A small patio area is furnished with a round table and four chairs. Lush green grass surrounds the building, and a winding brick path leads to the dock area by the water.
Cottage in Islesboro
5 out of 5 average rating, 108 reviews

Islesboro Boathouse

The Boathouse is on Gilkey Harbor with western views over the Camden Hills and spectacular sunsets. Full use of dock directly in front of the boathouse. Full beachfront access & many acres to explore! LGBT friendly. Harbor tour can be arranged at an additional cost.

Popular amenities for Islesboro holiday rentals

When is the best time to visit Islesboro?

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Avg. price$276 AUD$281 AUD$281 AUD$309 AUD$281 AUD$374 AUD$391 AUD$387 AUD$349 AUD$325 AUD$246 AUD$281 AUD
Avg. temp-7°C-6°C-1°C6°C13°C18°C21°C20°C16°C9°C3°C-3°C

Frequently Asked Questions

  • Are there family-friendly cottage rentals in Islesboro?

    Islesboro has more than 20 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Islesboro?

    Experience the best of Islesboro with our cabin rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly house rentals in Islesboro?

    Four-legged friends are welcome in Islesboro. Choose from more than 30 house rentals for guests traveling with pets.

  • Are there cottage rentals with a dedicated workspace in Islesboro?

    Yes! Work meets play with ease at over 10 cottage rentals in Islesboro featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do cabin rentals in Islesboro have air conditioning?

    Absolutely! We offer over 40 cabin rentals with air conditioning in Islesboro. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Islesboro have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in Islesboro. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Islesboro have a bbq area?

    Absolutely! We offer over 10 cottage rentals with a bbq area in Islesboro. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Islesboro have a gym?

    Absolutely! We offer over 30 cabin rentals with a gym in Islesboro. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Islesboro

  • Total holiday rentals

    Explore 220 holiday rentals in Islesboro

  • Nightly prices starting at

    Islesboro holiday rentals start at $84 AUD per night before taxes and fees

  • Verified guest reviews

    Over 7,380 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 100 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    210 of Islesboro holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Islesboro rentals

  • 4.8 Average rating

    Islesboro stays are highly rated by guests—averaging 4.8 out of 5!

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