Holiday houses in Islesboro

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.

Family · Value · Beach

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.

Family · Location · Quiet

Sweeping Views with Private Beach in Castine

Shore Cottage is a charming, rustic 1904 summer house on the water. Spectacular elevated views over the entrance to Castine's harbor. Watch seals and schooners from the deck or the glassed-in porch, which spans the entire waterside of the house. Descend the stairs and explore the rock pools on your own beach. A pleasant walk or short bike ride takes you to the delightful village of Castine, with restaurants, art galleries, shops. Kayaking, sailing, golf, and tennis are all available in town.

Value · Location · Outdoor spaces

"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.

Location · Family · Comfort

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.

Value · Family · Layout

"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.

Location · Nearby · Hospitality

#1 NE Small Coastal Town- Castine, Shell Cottage

Do you want to go to the #1 small town in the North East? Stay in a thoughtfully designed Maine woods cabin ideally located in a town which offers a true family camp. This Water Street location allows for a picture perfect getaway. Live like a summer person does and learn why they return each season from one generation to the next. Would you choose sailing lessons, golf, tennis, picturesque hikes, kayaking, museums, art classes, farmers markets and more to fill your ideal Maine day?

Location · Family · Hospitality

Silver Oak/Ocean Frontage

Beautiful new ocean front home. Located in Deer Isle. Private location. Yet close to everything Deer Isle/Stonington has to offer. There are three private king bedrooms and a fourth with six built into the wall extra-long twins. Three full baths. The master bath has a large walk-in shower, jacuzzi tub and dry sauna. Very tastefully decorated with almost every amenity a guest can imagine. Stunning views of the ocean from the kitchen, living room, dining room and master suite.

Family · Location · Quiet

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!

Value · Location · Decor

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 does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Family · Value · Backyard

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.

Family · Value · Indoor spaces

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.

Value · Family · Pets