Vacation rentals in Islesboro

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Top-rated vacation rentals in Islesboro

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Top guest favourite
A warm living area is showcased with wooden walls and ceiling beams. Large windows provide natural light and views of the surrounding trees. A teal sofa with orange pillows is positioned across from a decorative pouf. A black chair and a small side table complete the inviting space.
Cabin in Sedgwick
5 out of 5 average rating, 116 reviews

The Cabins at Currier Landing Cabin 1: Fern

Stylish Cabin w/Loft - Sleeps 3 - loft w/queen bed; 1st level twin daybed. 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 the Benjamin River Harbor shore. 2 seasonal cabins. 1 year round studio cabin. Centrally located on the Blue Hill Peninsula, near Deer Isle, the cabins offer access to outdoor activities, cultural events, restaurants & shops.

Top guest favourite
A scenic view captures a grassy area leading to a dock over Hobb's Pond. Four red Adirondack chairs are arranged around a fire pit made of stones. A mountain rises in the background, framed by fluffy clouds in a blue sky.
Cabin in Hope
4.97 out of 5 average rating, 127 reviews

Hobb’s House - Year Round Log Cabin on the Water

Cozy 2 Beds, 1 pullout sofa bed, 2 Bedroom, 2 Bath Log Cabin with water/mountain views on Hobb’s Pond. Relax on the dock, grill from the deck, canoe (1)/kayaks (2)/swim during the day and relax with your streaming services on the smart TV at night. 5min drive to the Camden Snow Bowl for ski/snowboard during the winter. Ice skate on the pond. Rent out a boat during your stay. 13 min drive to downtown Camden for great restaurants and a sunset cruise on a sailboat. Close proximity to hiking trails!

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, 432 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
The image captures a serene view of the water at sunset, with the sun reflecting on the surface. Framed by lush green foliage, a small rustic bench is positioned on the shore, inviting quiet moments of contemplation.
Cottage in Belfast
4.97 out of 5 average rating, 194 reviews

Quiet cottage on the bay

Settle in at this mid-coast Maine treasure, where you will find more than you hoped for in a getaway. Located in a private neighborhood and setback on a private road on 2.5 acres. You can take a short stroll down a wooded path to the Belfast bay and watch the sunset or simply enjoy the view from living room. The rocky beach gives you access to a wonderful piece of the Maine coastline. Come make some memories at this unique, pet and family-friendly quiet cottage just 1 mile to downtown Belfast.

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

Exquisitely Modern Stargazing Cottage @Diagonair

Romantic and luxurious, this 2,000 square foot modern cottage nestled on twelve acres is a favorite of honeymooners and lovers of modern design * 1 hour to Acadia National Park & Bar Harbor; 15 minutes 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

Top guest favourite
A spiral staircase crafted from natural wood ascends to a loft area, featuring rounded steps that maintain the organic shape of the wood. A window nearby offers natural light, illuminating bookshelves filled with various volumes and a map hanging on the wall.
Cabin in Hope
4.98 out of 5 average rating, 366 reviews

Hand built cabin overlooking a pond

Beautiful hand built cabin, overlooking Cotton Pond. Ten minutes from Camden, the sailing mecca of the east coast. Solar lights, (we are off the grid) gravity fed kitchen water, gas-hot water outdoor shower, outhouse overlooking the forest. Hiking trails everywhere! Swimming across the road on Hobbs Pond. If you book in November, there is a possibility that if it gets cold, you will not have a hot outdoor shower and will use water from a 5 gallon ceramic container for drinking and cooking.

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, 413 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
Two Adirondack chairs are positioned on a grassy area in front of a small cabin with a green metal roof. Lush greenery surrounds the cabin, providing a serene and natural setting.
Guesthouse in Lincolnville
4.98 out of 5 average rating, 443 reviews

"The Lair" Guesthouse

"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee and tea everyday, all day! We are closed for Winter, will re-open Mid-April. Thank you.

Top guest favourite
A two-story red building features a sloped roof with solar panels, surrounded by lush greenery. An outdoor area includes a picnic table and several chairs, offering a tranquil space for relaxation. A garage door can be seen, blending seamlessly with the rustic aesthetic.
Apartment in Belfast
4.98 out of 5 average rating, 350 reviews

Room with a Brew

Welcome to our new building. "A Room With a Brew" is located above Belfast's newest craft brewery, Frosty Bottom Brewing. A small community supported brewery open 2 days/week for 3-4 hours for beer share members. Guests can request a tour of the brewery and sample some fresh beer. Owners live in downtown Belfast and are available should any issues arise during your stay. The apartment/brewery is located 3 miles from downtown on a quiet road that offers local hiking and biking.

Top guest favourite
A newly constructed cottage is nestled among trees, featuring a screened porch with wooden rocking chairs. The entrance is defined by a bright red door, inviting guests to enjoy the surrounding natural beauty. Gravel pathways lead to the entry, with a lawn area visible.
Cottage in Lincolnville
5 out of 5 average rating, 129 reviews

Rocky Top Hideaway with level 2 charging station.

Feel the magic in this quiet secluded hillside retreat. Awaken your senses with the smell of the salt air, pines and an occasional whiff of coffee beans roasting all while watching the ferry go back and forth to Ilesboro. Early risers will enjoy spectacular sunrises. Experience nature without being too far off the beaten path. A private half mile walk down the driveway will end at brick sidewalks leading you to Lincolnville Beach, one of Maine's stretches of sandy shoreline.

Top guest favourite
A screened porch offers a view of Penobscot Bay, featuring two green wicker chairs adorned with floral cushions. The scenery includes a lush lawn and Adirondack chairs positioned for relaxation, with water visible in the background and distant hills framing the horizon.
Cottage in Belfast
4.99 out of 5 average rating, 154 reviews

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

Top guest favourite
An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.
Cottage in South Thomaston
4.96 out of 5 average rating, 202 reviews

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Popular amenities for Islesboro vacation rentals

When is the best time to visit Islesboro?

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Avg. price$266 CAD$272 CAD$272 CAD$299 CAD$272 CAD$361 CAD$378 CAD$373 CAD$337 CAD$314 CAD$238 CAD$272 CAD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Islesboro?

    Islesboro has more than 150 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Islesboro with our house rentals, starting at about $80 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 vacation rentals in Islesboro?

    Four-legged friends are welcome in Islesboro. Choose from more than 100 vacation rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 120 vacation 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 cottage rentals in Islesboro have wifi?

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

  • Do house rentals in Islesboro have a bbq area?

    Absolutely! We offer over 30 house 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 230 vacation rentals in Islesboro

  • Nightly prices starting at

    Islesboro vacation rentals start at $95 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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