House holiday rentals in Islesboro

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Top-rated house rentals in Islesboro

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Top Guest favourite
A charming modern cottage with a red exterior and a pitched roof stands amidst lush greenery. The covered porch is furnished with comfortable seating, inviting relaxation. Large windows allow natural light to enter, enhancing the welcoming atmosphere of the property.
Home in Northport
4.98 out of 5 average rating, 224 reviews

Cute Midcoast Cottage w Hot Tub

Kick back and relax in this ideally located modern cottage. Enjoy a soak in the hot tub or the peace of the covered porch. Situated in the heart of midcoast Maine, this cottage has it all. An elegant kitchen that awaits your culinary delights, a spacious living area, a primary bedroom with a TV, a kingsize bed and a luxurious bath with a soaking tub and a walk-in rainfall shower, plus twin bunk beds for the kiddos. A small store and a farm to table restaurant are conveniently across the street.

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, 135 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 12 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Guest favourite
The spacious kitchen features modern appliances and a large granite island with bar stools. Light wood paneling and flooring create a warm atmosphere. A comfortable living area with seating is visible, along with large windows that provide views of the surrounding outdoors.
Home in Belfast
4.9 out of 5 average rating, 112 reviews

Entire House/Mill/modern vintage on 35 Acre Pond

The house has a access trail to 35 acre Mason Pond. This newly built home has an abundance of open space with native wood walls and ceilings. The kitchen and living room is on the second floor capturing views of surrounding hills and distant ocean. 2nd fl A/C only .The second floor has sliding glass doors opening to a 36 ft covered deck.The 2 bedrooms are on the 1st floor with queen size beds. Both bedrooms have 10 foot ceilings with their own private French doors access to yard & 6 acre field

Guest favourite
A comfortable living area features a green sofa paired with a rustic wooden coffee table. Sunlight streams through two large windows, illuminating the light-colored walls and warm wooden floors. An air conditioning unit is mounted on the ceiling, and there is a cozy armchair in the corner.
Home in Liberty
4.88 out of 5 average rating, 101 reviews

Modern Lakefront Home w/ Hot Tub • Winter Escape

Grace's Cottage is a charming 1860's cottage on Lake Saint George. Newly remodeled, the 3 bedroom, 1 bath cottage offers a perfect blend of old-world charm and modern amenities. A spacious screened porch overlooks the lake, and a year-round hot tub provides a perfect spot to relax & unwind. This living space is perfect for gathering with family & friends. Whether you're seeking a romantic getaway or a fun-filled family vacation, Grace's Cottage is the perfect home base for your Maine adventure.

Top Guest favourite
The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.
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
The exterior of a classic New England style home features white siding and green shutters. A stone pathway leads to the entrance, surrounded by well-maintained shrubs and trees. The structure includes multiple windows, complementing its inviting design in a serene setting.
Home in Camden
5 out of 5 average rating, 217 reviews

Quaint 3 Bedroom In Town Camden Home

Our 1900’s New England style home is located in a quiet neighborhood less than a mile from the heart of downtown Camden. Midcoast Maine is home to many great restaurants, shops, and art galleries, as well as events such as the National Toboggan Championships, North Atlantic Blues Festival, Maine Lobster Festival, and more! With Rockland just a quick 15 min. drive and Belfast located approximately half an hour north, you’ll be in a prime location to experience everything this area has to offer.

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

Guest favourite
Home in Stonington
4.92 out of 5 average rating, 101 reviews

Bayview House 1br 2ba Stunning Harbor Views

Do you crave balmy summer evenings or frosty winter days that make you feel like you've been transported back to a simpler time? Or long for days spent on the water or experiencing village life with friendly locals in charming pubs tasting local eats? Experience the simple joys of life with rustic yet modern amenities offered at this coastal 2-story home. Whether daily strolls by the water or taking in the sunset on your deck, you'll fall in love with this lovely New England destination.

Guest favourite
A view from a shaded patio showcases a round table surrounded by wicker chairs. The lush green lawn extends to the water's edge, where trees provide a natural frame for the serene expanse of the bay, dotted with clouds reflecting in the distance.
Home in Belfast
4.92 out of 5 average rating, 208 reviews

[Trending Now]Belfast Ocean Breeze

Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal town of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, and boasting breathtaking views of Penobscot Bay and beyond. The exceptional grounds offer an ideal setting for relaxation with the added allure of explorations along the shoreline or tennis/ pickleball at park/ year round hot tub. Near downtown and Rt. 1. No parties.

Guest favourite
A dining area is illuminated by natural light, featuring a dark wooden table with a decorative centerpiece of fruit. Large windows offer a view of the water and nearby boats, while comfortable seating is arranged alongside the table.
Home in Cushing
4.93 out of 5 average rating, 162 reviews

Dockside Retreat - Winter Openings

This beautiful, newly renovated home is three bedrooms and two bathrooms, with an open living and dining room waiting to give your family or group of friends the ideal Maine vacation experience! On site parking, a lovely yard, a new sauna on a beautiful deck overlooking the water, nearby fields and steps away from the famous Olson House on one side, you can sit on the deck and overlook the working lobster wharf with fishermen coming and going daily on the other side!

Top Guest favourite
The exterior of a charming yellow house is presented, featuring white stairs leading to a green front door with an ornamental design. Lush shrubs frame the entrance, and tall trees provide shade to the vicinity, creating a welcoming appearance.
Home in Waldoboro
4.99 out of 5 average rating, 105 reviews

1830s Cape hosted by George & Paul

This 1830 cape is for rent by the month or weekly or for a two-night minimum stay. It is located at the edge of the historic village of Waldoboro. It offers a convenient base to sightseeing in midcoast Maine. It’s old-fashioned, decorated with plants, antiques and paintings and features a large, fully equipped kitchen, music room with piano, television room with pull-out sofa, full bath with stall shower and outside patio. Your hosts are right across the driveway.

Top Guest favourite
The exterior of the home is featured, showcasing a single-story structure with a light grey façade. A brick pathway leads to the front entrance, accompanied by well-maintained lawns and decorative flower beds. Surrounding trees provide a natural setting, enhancing the peaceful atmosphere.
Home in Rockport
4.95 out of 5 average rating, 349 reviews

Sweet home away (pet friendly)

Single floor living at its finest. Conveniently located to both Camden and Rockland, enjoy this 3 bdrm 1.5 bath home in a great country setting. Just 1/2 mile to route 1 and very close to the ocean. Come enjoy the large back deck over looking the peaceful maine woods. The front door in about 50’ from the road, which can be busy at certain time of the day. There is 1 ring doorbell for everyone’s security outside the front door of the house.

Popular amenities for Islesboro house rentals

When is the best time to visit Islesboro?

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Avg. price$416 NZD$416 NZD$416 NZD$449 NZD$416 NZD$557 NZD$582 NZD$582 NZD$574 NZD$561 NZD$491 NZD$374 NZD
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Quick stats about house rentals in Islesboro

  • Total holiday rentals

    Explore 70 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 2,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Islesboro holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Islesboro rentals

  • 4.8 Average rating

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

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