Holiday houses in Islesboro

4.98 out of 5 average rating, 274 reviews

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

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.

LocationValueCleanliness

4.97 out of 5 average rating, 66 reviews

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

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.

LocationValueHiking

4.97 out of 5 average rating, 76 reviews

Home in Brooksville

Above & Beyond: Beautiful home on Penobscot Bay

Experience beautiful coastal Maine at this stunning 2-bedroom, 2-bath Harborside waterfront vacation home with private beach. Guests enjoy the newly renovated modern interior, high-end furnishings, gourmet kitchen, outdoor fire pit, media room, European soaking tub -- plus the privacy of a huge deck overlooking stunning Penobscot Bay. Enjoy hiking in Holbrook Island Wildlife Sanctuary, launch a kayak from your private beach, star gaze under dark skies, or relax and enjoy being away from it all.

LocationValueParks

4.98 out of 5 average rating, 212 reviews

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

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.

FamilyValueBeach

4.94 out of 5 average rating, 107 reviews

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

"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

LocationFamilyView

Superhost

Home in Northport

"Seaswept" Oceanfront Cottage on Penobscot Bay

Introducing "Seaswept." New to the 2026 rental market, this spectacular oceanfront retreat offers panoramic views of Penobscot Bay and breathtaking sunrises from nearly every room. Featuring 4 bedrooms, 3 full baths, a private shoreline, expansive waterfront deck, and a cozy fire pit by the water, Seaswept blends timeless coastal charm with modern comfort. Enjoy the peaceful setting while being in close proximity to Bayside village, Camden, Belfast, and all that Midcoast Maine has to offer.

LocationFamilyAmenities

5.0 out of 5 average rating, 4 reviews

4.95 out of 5 average rating, 65 reviews

A charming light-colored condo is displayed, featuring a mix of shingle and clapboard siding. Vibrant flowers and greenery surround the entrance, which is framed by a white picket fence. A bright blue door stands out, and an American flag gently flutters in the breeze.

Home in Stonington

Stonington Dream House

Welcome to Schooner! Schooner is a light filled, first floor condo that lives like a single family home. LOCATION * LOCATION * LOCATION the home overlooks Main Street, Stonington Harbor and the gorgeous archipelago beyond. Enjoy all of this charming coastal town. Walk everywhere! Coffee house, library, restaurants, museum, opera house, charming shops, plein air painters, photographers, cool art around town and more. This is what coastal Maine dreams are made of. We love to share this town!

FamilyLocationAccuracy

5.0 out of 5 average rating, 112 reviews

A charming single-story cottage is surrounded by a lush green lawn. Large windows allow for ample natural light, and flower beds with colorful blooms adorn the entrance. A serene landscape with distant hills completes the tranquil scene under a partly cloudy sky.

Cottage in Lincolnville

Sunny 2 Bedroom cottage - Walk to the beach!

Single story cottage in the heart of Midcoast Maine! This 2 bedroom cottage is in the Lincolnville Beach area. Located within eyesight and walking distance of the public beach, the Islesboro Ferry terminal, McLaughlin’s restaurant, and the Beach Store. Property is located on US route 1- just 6 miles north of Camden (8 minute drive), and less than 15 minutes south of Belfast. This year-round cottage provides a lovely retreat for resting while exploring all the Midcoast has to offer.

FamilyValueBeach

5.0 out of 5 average rating, 36 reviews

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

"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.

LocationBarbecueHiking

The Victorian cottage, painted in a soft yellow hue, is surrounded by lush greenery. A meandering pathway leads to the welcoming front porch, flanked by flowering shrubs. A white picket fence frames the yard, offering a charming entrance to the well-maintained garden.

5.0 out of 5 average rating, 26 reviews

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and character of the home while integrating sophisticated elements throughout. Prime location within walking distance to local coffee shop, ice cream parlor and charming gift shop. All points of island are within a 10 minute drive of the home. Massive, private bedrooms perfect for multiple couples or families. Reach out with any questions or concerns you may have!

LocationValueCleanliness

4.98 out of 5 average rating, 54 reviews

The exterior showcases a modern home featuring a metal roof and large windows. Stone steps lead to a landscaped yard filled with native plants and large boulders. A patio with seating invites relaxation while offering expansive views of the surrounding natural landscape.

Home in Northport

Cliff House - Ocean Views! Architectural designed.

Imagine a home as captivating as its landscape; one where the rolling ocean views and rising morning mist complement the allure of this particular design. A home where the floorplan has been constructed to let the natural world inside. This property is a true masterpiece; from the use of triple pane windows, private balconies, and a custom crow's nest, to the intricate masonry, 2- person hot tub (Spring, Summer, and early Fall use only), and fire pit patio.

LocationFamilyHospitality

5.0 out of 5 average rating, 43 reviews

An aerial view captures the waterfront cottage nestled among lush trees along the Bagaduce River. The expansive greenery surrounds the property, leading to serene water along the shore. The distant Blue Hill mountain is visible under a clear sky, providing a tranquil backdrop for this secluded retreat.

Home in Brooksville

Casa on the Bagaduce River

Escape to this charming 2-bedroom, 2-bathroom waterfront cottage on the Bagaduce River in Brooksville, Maine. Perfect for up to 5 guests (1 king, 1 queen, 2 twins), this cozy retreat offers panoramic views of the river and Blue Hill mountain, an auxiliary wood-burning stove, claw-foot tub, modern kitchen, Wi-Fi & flat-screen TV. Enjoy relaxing on the riverfront deck. Close to nearby trails and Acadia National Park, it's an ideal spot for nature lovers.

FamilyLocationPets

Popular amenities for Islesboro holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Islesboro

5.0 out of 5 average rating, 10 reviews

The exterior of a classic cottage is depicted, showcasing a shingled roof and multiple gabled windows. Surrounding the house, a well-maintained lawn features shrubs and greenery. A gravel driveway leads up to the entrance, with trees visible in the background.

Cottage in Islesboro

Surrounded by Water

LocationViewBiking

5.0 out of 5 average rating, 4 reviews

The Colony

FamilyQuietAccess

5.0 out of 5 average rating, 14 reviews

A spacious deck is visible, adorned with a wooden picnic table and wicker seating. Vibrant orange flowers and lush greenery frame the scene, leading to sweeping views of the calm water and distant trees under a clear sky.

Cottage in Islesboro

Beautiful Cottage on Island Bluff & Beach

FamilyLocationGetting around

A two-story home features a symmetrical façade with a centrally located front door and three windows on each side. A covered porch is visible on the left, with logs stacked beside it. Lush greenery surrounds the house, enhancing the natural setting.

5.0 out of 5 average rating, 12 reviews

Island Retreat

FamilyLocationCondition

4.81 out of 5 average rating, 58 reviews

The cottage exterior is shown, featuring rustic wood siding and a welcoming front porch. A house number is visible on a tree, and colorful plants are placed on the porch. Lush greenery surrounds the space, enhancing the natural setting.

Cottage in Islesboro

Ocean Front Island Cottage

FamilyLocationHeating

A charming porch entrance features a light green wall adorned with a decorative sign reading 'The Gables.' A basket of flowers hangs beside a comfortable wicker chair with a striped pink cushion, inviting guests to relax and enjoy the pleasant surroundings.

4.89 out of 5 average rating, 85 reviews

"The Gables" on Penobscot Bay, Mid-Coast Maine

LocationFamilyBackyard

5.0 out of 5 average rating, 4 reviews

3+ Bedroom on the water with dock.

KitchenHospitalityNearby

A two-story farmhouse structure is visible, featuring a light-colored exterior with multiple windows and a sloping roof. Lush green grass surrounds the house, and trees provide partial shade. The background includes a glimpse of water and a clear blue sky with scattered clouds.