Vacation rentals in Islesboro

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Top-rated vacation rentals in Islesboro

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite
A rustic cabin is nestled among vibrant trees along the shoreline of a calm lake. A wooden dock extends into the water, providing access. The natural surroundings create a serene atmosphere, with greenery reflecting on the lake's surface.
Cabin in Jefferson
4.88 out of 5 average rating, 129 reviews

Loon Lodge

Located on beautiful Damariscotta Lake, "Loon Lodge" is a rustic cabin from another era. Fall asleep to the sound of crickets and frogs and wake every morning to the call of the lake's many loons. The cabin is 30 minutes from Augusta and 15 minutes from Damariscotta. Hiking enthusiasts will enjoy climbing the Camden Hills-a quick 45 minute drive from the lake. You’ll love my place because of the views, the ambiance, the people, and the location. My place is good for couples and solo adventurers.

Top guest favourite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 430 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top guest favourite
An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.
Home in Hampden
5 out of 5 average rating, 140 reviews

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

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.

Top guest favourite
A modern cabin exterior is framed by large glass doors, providing a view into a simple dining area with natural wood flooring. A wall-mounted hook holds a hat, while a mix of chairs and a round table creates an inviting space bathed in natural light.
Home in Georgetown
4.99 out of 5 average rating, 109 reviews

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Top guest favourite
A charming New England cottage from the late 1800s is visible, featuring white siding and multiple gabled roofs. The yard includes well-maintained grass and shrubbery. The structure is adjacent to a road, with power lines overhead, and a small cabin can be seen behind the main house.
Home in Lincolnville
4.94 out of 5 average rating, 102 reviews

"The Roost" Cottage

"The Roost" is a bright 1400 sqft. 2 bedroom c.1890 cottage that has been recently renovated and painted located on a two acre property with a coffee roaster Green Tree Coffee and Tea as well as another very small cabin called "The Lair". We are located 400 yards from Lincolnville Beach, 2 miles from Mt. Battie State park, 4 miles from downtown Camden, and 12 miles from Belfast. We are a very dog friendly property, plenty of room for your dog to roam out back in small pasture. Sorry no cats

Top guest favourite
A modern cabin is nestled among trees, supported by stilts within the forest. Sunlight filters through the foliage, highlighting the cabin's wooden exterior and windows. The surrounding greenery creates a serene, natural setting that offers a sense of privacy and tranquility.
Cabin in Sedgwick
4.98 out of 5 average rating, 104 reviews

The Cabins at Currier Landing Cabin 3: Pine

Relax in this stylish, cozy & bright queen bed studio cabin. The Cabins at Currier Landing - featured in Dwell as “Three Magical Tiny Cabins Take Root in a Maine Forest” - are located on the Thos. Currier Saltwater Farm. Glimpses of water & access to 300’ of our shore on the Benjamin River Harbor. 2 seasonal cabins. 1 year round studio cabin. Centrally located on the Blue Hill Peninsula, near Deer Isle, the cabins afford access to outdoor activities, cultural events, restaurants & shops.

Top guest favourite
A bright living area features two comfortable wicker chairs and a round coffee table, all positioned to take in panoramic waterfront views through large windows. A cozy area rug anchors the space, while a decorative bowl and outdoor binoculars are visible on the table.
Place to stay in Stockton Springs
4.98 out of 5 average rating, 100 reviews

Acadia Region New Oceanfront Cottage

Relax and unwind at this unique waterfront retreat where you can enjoy breathtaking views of the ever-changing tides. Keep an eye out for bald eagles, osprey, and the occasional seal as you soak in the natural beauty around you. This renovated former boathouse combines comfort with convenience, offering the perfect base for your coastal adventures. Situated in Mid Coast, Maine, it's ideally located just an hour from Acadia National Park, 15 minutes from Belfast, and 45 minutes from Camden.

Top guest favourite
The cottage is surrounded by a large, lush green yard, with a serene landscape featuring trees and shrubs. A generous blue sky provides natural light, emphasizing the relaxed atmosphere. The unique architecture of the cottage is highlighted by large windows and a spacious deck.
Cottage in Lincolnville
4.92 out of 5 average rating, 409 reviews

Eco-friendly studio - ocean views, close to beach

Sunny eco-friendly cottage on Route 1, steps from the beach! A cozy studio with a Murphy bed, a full bath, and kitchenette - stovetop, fridge, toaster, & microwave. Beautiful views of Penobscot Bay – don't worry, the blinds will keep the sunshine at bay when you need a nap! You're within easy walking distance of sandy beaches, restaurants, shops, a coffee roaster, and a market. Explore nearby hiking trails, Mount Battie, and the charming towns of Belfast, Camden, Rockport, and Rockland.

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
Bungalow in Sedgwick
4.99 out of 5 average rating, 234 reviews

Exquisitely Modern Stargazing Cottage @Diagonair

Romantic and secluded, this 2,000 sf modern luxury cottage nestled on twelve acres is a favorite of honeymooners and lovers of modern design * One hour to Acadia National Park & Bar Harbor; 15 min to shopping, hiking, swimming * Stargazing deck * 2 full baths, one with steam shower * Fully equipped kitchen with under-counter fridge/freezer * Two gas fireplaces, one indoors, one on a covered deck * Queen bed with luxurious linens and pillows * WIFI, streaming TV, grill, bar * EV charger

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.

Popular amenities for Islesboro vacation rentals

When is the best time to visit Islesboro?

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Avg. price$273 CAD$279 CAD$279 CAD$306 CAD$279 CAD$371 CAD$387 CAD$383 CAD$345 CAD$322 CAD$244 CAD$279 CAD
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 vacation rentals in Islesboro

  • Total vacation rentals

    Explore 220 vacation rentals in Islesboro

  • Nightly prices starting at

    Islesboro vacation rentals start at $84 CAD per night before taxes and fees

  • Verified guest reviews

    Over 7,380 verified reviews to help you choose

  • Family-friendly vacation rentals

    150 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 100 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    210 of Islesboro vacation rentals include wifi 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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