House holiday rentals in Islesboro

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private sanctuary where tranquility meets luxury. Our Coastal Maine Cottage home is perched on a granite ledge that disappears twice daily with the rising tide. Enjoy the pristine interior bathed in natural light, cherry floors, and gourmet kitchen. Wake to panoramic views of the Penobscot River from the owner's suite. Conveniently located 12 minutes to downtown Bangor, our retreat offers easy access to urban amenities, an international airport, and Acadia! IG @cozycottageinmaine.

4 BR Waterfront Unique House + Dock! [Osprey Cove]

Osprey Cove is a unique vertically built home that has fantastic views of the top of Somes Sound. A dock, firepit & gazebo are available for use and are shared with the neighboring unit, which are always a guest favorite! A spiral staircase brings guests to all levels of the home and you will find the home fully stocked as the homeowners use this space themselves to vacation! -10 min to Southwest Harbor -13 min to Acadia National Park [Cadillac Mountain Entrance] -17 min to Downtown Bar Harbor

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

The Gables is a historic cottage built in the mid-late 1800's and has always been family owned. The 2+ acre property is located on a quiet road surrounded by cottages built by our great great grandfather. The Gables comes with its own private beaches, a lawn for yard games, a hammock for naps and a porch overlooking the bay. We can put you in touch with a local fishermen for fresh lobster or mussels. Check the ferry schedule-see photos. www.townofislesboro.com/special-pages/getting-here

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 privacy and 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.

Lavender by the Sea

The Cottage rests over the end of Penobscot River as it opens into the Bay. The Cottage will comfortably accommodate two. The Cottage has a spacious bedroom, full kitchen, dining area, den and an all season porch with rockers. From Cottage there are views of the water and the lavender gardens. The gardens are terraced with a path down to the sea. The Carriage House Suite is available for an additional fee. it has has two bedrooms, a full bath and a sitting area. It can easily sleep four.

SunnySide - Cottage w/ Pen Bay Views in Bayside

Welcome to Sunny Side Cottage, in the heart of Merithew Square in historic Bayside! This Victorian Cottage has been lovingly restored, combining coastal charm with modern amenities for a memorable and comfortable stay. Boasting a large, wrap around porch and a second floor balcony, you will always find the perfect spot to sit and enjoy a cup of coffee or watch the working bay hum along. Located 4 minutes from the Northport Yacht Club, don't miss your chance to enjoy the summer in Maine!

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!

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.

Intown Camden, 2 bedroom, 2nd floor, own entrance

Restaurants, shopping, and the harbor are a five-minute walk from one of the oldest capes in Camden village. House was built in 1800 on a quiet one-way street. The second-floor apartment has a private entrance and includes one bedroom with a queen-size bed, and a sitting room with a single bed, a seating area, t.v, . Wifi access. Private outside garden with own entrance. Minimum 3 night stay - 10% off for full week stays.