Holiday houses in Islesboro

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Top-rated holiday 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
A charming blue cottage is set in a lush green landscape, surrounded by trees and colorful flower beds. A brick chimney rises from the home's side. In the foreground, a cluster of large stones is visible on the well-kept lawn.
Guesthouse in Orland
4.99 out of 5 average rating, 190 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 800 Mbs fiber internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. We’re very pet friendly!

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, 137 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
Apartment in Hancock
4.98 out of 5 average rating, 306 reviews

Flower Farm Loft

When you arrive at the Flower Farm Loft you're greeted by our dogs, who will likely jump on you with muddy paws and request fetch and pets. You're immediately surrounded by flowers in our gardens and flower studio. The loft has big east facing windows that look over our farm and surrounding fields. You'll open the curtains in the morning to incredible sunrises over Kilkenny Cove, and end your nights at your private fire pit with immaculate star filled skies that will make it hard to go inside.

Guest favourite
A comfortable living space features a gray sofa adorned with decorative pillows, paired with two blue armchairs. A wooden rocking chair and a low coffee table are present, with artwork displayed on the walls. Natural light filters in through the multiple windows.
Apartment in Hope
4.89 out of 5 average rating, 107 reviews

Bright, new apt near coastal villages!

Enjoy this country setting on Hatchet Mountain in Hope near the Maine coast, about 8 miles from Camden. Hobbs Pond (2 miles long!) is just a mile away with public access for swimming, boating, and kayaking. Loads of hiking trails surround us, too. Beaver Lodge, a favorite spot for weddings and other family events, is also nearby. The Camden Snow Bowl, a year-round recreation area offers hiking, mountain biking, skiing (with ocean views), and more! This listing has an exemption for all animals.

Top Guest favourite
A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.
Cottage in Brunswick
5 out of 5 average rating, 203 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

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, 406 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
Apartment in Belfast
4.97 out of 5 average rating, 406 reviews

Belfast Harbor Loft | Downtown

Come and experience the peaceful, yet vibrant, atmosphere of Belfast! This downtown loft is a great place to stay, being just two blocks away from the beach. Enjoy the morning light in the two bedrooms, both facing the harbor, while the living room offers a stunning view of Main Street. The loft is full of character, with its refurbished floors, exposed brick and rafters, large windows, and newly renovated kitchen and bathroom. Make yourself at home in a calm and inviting atmosphere.

Top Guest favourite
A charming yellow house features white trim and a welcoming front door. Flower boxes are filled with vibrant blooms beneath the windows, surrounded by a neatly tended garden. A stone wall provides a defined border, enhancing the inviting exterior.
Guest suite in Rockland
4.98 out of 5 average rating, 476 reviews

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. *SHARED wall between studio and main house, therefore some shared noise. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOG

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
The exterior of a cozy cabin is showcased, featuring wooden shingles and a dark roof. A small deck includes a two-chair dining set and a hot tub nearby, surrounded by lush greenery and a well-maintained lawn.
Cabin in Searsmont
4.99 out of 5 average rating, 191 reviews

Birch Hill Cabin w/Hot Tub

Birch Hill Cabin is set on the side of a hill, surrounded by almost 8 acres of woods. The cabin is 288 square feet, and the bathroom is detached and located approximately 20 feet from the cabin. A hot tub is conveniently located off the deck for ultimate relaxation! This cabin is tucked away, surrounded by nature! But also conveniently located to so many wonderful spots in the Midcoast! Come enjoy the peace and quiet, where you can rest and recharge!

Top Guest favourite
A modern cabin is set against a backdrop of tall pine trees, featuring large windows that invite natural light. The exterior showcases a wooden deck with a seating area, complemented by a staircase leading to the entrance.
Cabin in Penobscot
4.97 out of 5 average rating, 158 reviews

Modern Cabin in the Pines • Hot Tub + Near Acadia

Enjoy our cozy home-away-from-home amid towering pines and granite boulders — the perfect respite after exploring Acadia. Our newly built cabin has rustic Maine charm and modern comforts: AC, waterfall shower, memory foam mattresses, indoor gas fireplace, outdoor gas fire pit, gas grill, hot tub, 4KTV, high-speed internet, modern kitchen, filtered water, gas range, high-end appliances, and front-loading washer/dryer.

Popular amenities for Islesboro holiday rentals

When is the best time to visit Islesboro?

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Avg. price$328 NZD$335 NZD$335 NZD$368 NZD$335 NZD$445 NZD$465 NZD$460 NZD$415 NZD$386 NZD$293 NZD$335 NZD
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Frequently Asked Questions

  • 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 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.

  • 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.

  • Do cottage rentals in Islesboro have air conditioning?

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

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

    Yes! Work meets play with ease at over 40 cabin rentals in Islesboro featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly cottage rentals in Islesboro?

    Four-legged friends are welcome in Islesboro. Choose from more than 10 cottage rentals for guests traveling with pets.

  • 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.

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

    Experience the best of Islesboro with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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 $100 NZD 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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