Holiday rentals 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.

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 guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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.

"Bohemian Bungalow" Studio Island Guest Cottage

Enjoy a peaceful getaway in this cozy cottage. Centrally located on Islesboro, the "Bohemian Bungalow" provides easy access to everything the island has to offer. Walk to nearby beaches, tennis courts, or the Historical Society, which hosts art shows, lectures, and other events. The studio sleeps two on a full-size futon sofa, and features a kitchenette, spacious bathroom, and outdoor dining area. Eco-minded host supplies line-dried linens, organic coffee, and plant-based breakfast items.

Charming Harbor Private One Bedroom

Situated just above a stream just off Rockport Harbor, this quiet, small one-bedroom apartment has its own private entrance and small deck. Located on the back side of RAYR wine and cheese shop, this charming apartment is within a 10-minute walk of two wonderful restaurants in the village of Rockport, 18 Central and Nina June, as well as a lunch spot and a deli. A wonderful getaway space for couples and solo adventurers, you’ll love it because of the location, ambiance, privacy and charm.

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.

Milk House

nice little vacation cottage in Dark Harbor, near to everything. queen sized bed, so sleeps up to two in a quiet island location for short or medium term stays. most reasonable amenities provided; hiking or social recommendations are available on request. (Wi-Fi speeds are excellent, although I was not able to use AirB&B's official Wi-Fi measurement option.) *Please be aware, this property is on an island, which must be accessed by boat or ferry, so service can be interrupted.

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!

Islesboro Island Oceanfront Cottage

Take it easy at this unique and tranquil getaway. This cottage is on the Island of Islesboro, accessed by car ferry from Lincolnville, private plane, or private boat. Located at the end of a mile long, private road, this guest house is situated right on the shorefront on West Penobscot Bay. It shares a driveway that accesses this cottage and the owner’s home. Watch sailboats and eagles from the front porch. Fall asleep to the sound of the waves.