Vacation rentals 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.

Birch Cottage · Just You & Quantabacook Lake

Kick back and relax in this serene, stylish, and newly renovated space. Birch Cottage is the perfect rustic waterfront getaway--a retreat for couples and solitude seekers. Unwind and escape to this enchanting, woodsy, lakefront property on gorgeous Quantabacook Lake. Cottage is ideal for both romantic couple retreats and peaceful solo excursions. Nestled among tall pines and just feet from shore, this magical haven offers breathtaking views and a tranquil atmosphere for your holiday getaway.

The Cabins at Currier Landing Cabin 3: Pine

Relax in this stylish, cozy & bright queen bed studio cabin. The Cabins at Currier Landing - featured in Dwell as “Three Magical Tiny Cabins Take Root in a Maine Forest” - are located on the Thos. Currier Saltwater Farm. Glimpses of water & access to 300’ of our shore on the Benjamin River Harbor. 2 seasonal cabins. 1 year round studio cabin. Centrally located on the Blue Hill Peninsula, near Deer Isle, the cabins afford access to outdoor activities, cultural events, restaurants & shops.

Megunticook Retreat

HOT TUB AVAILABLE MAY 15-OCT 15 ‼️CURRENTLY OPEN‼️ Our cottage is right on Megunticook Lake! With swimming, boating and mountain views, this is the perfect place to relax and unwind. We are walking distance to Camden Hills State Park, and a 5 minute drive to downtown and the ocean. Come for adventure, shopping, gourmet restaurants, hiking, skiing, or romantic sunset sails on a local schooners. There is something for everyone in this beautiful area. Come see it for yourself! ‼️NO PETS‼️

"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.

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!

Modern Cabin on Crie Hill

Unwind at this secluded hillside hideaway. Perched above the valley with sweeping ridge views, this newly built cabin blends comfort with privacy. Begin your day soaking in the outdoor tub as morning mist drifts up from the valley below, or gather around the granite fire pit in the evening while grilling under the open sky. Designed with sustainability in mind, the retreat runs on solar power backed by a quiet propane generator to ensure a worry-free stay even on cloudy days.

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

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.

Hilltop Retreat

Visit our off-grid hilltop retreat in Northport, Maine, with stunning 180-degree views of Penobscot Bay, Isleboro, Blue Hill, and Acadia National Park. The house has two bedrooms, a bathroom, a kitchen, and a sunroom. Gardens with seasonal produce. Powered by solar energy with backup generators, it offers high-speed internet for work. Perfect for a peaceful getaway with beautiful scenery and amenities for all ages.

Antique Barn Apartment at Salt Water Farm

This elegant and comfortable apartment in situated in an antique post & beam barn that sits perched above rolling fields and vegetable gardens looking out over the Penobscot Bay. From the porch, guests can watch the local lobsterman pick up traps and see schooners weaving through the islands. The apartment sits over Salt Water Farm Cooking School, a small recreational cooking school for home cooks.

Double On The Rocks, ocean view family retreat

Newly renovated duplex ( 3/2 and 4/2) for families and friends that love traveling together and want to share the adventure but not every waking minute, the home allows for everyone to find their own space. Enjoy fantastic ocean views while relaxing around the fire and playing yard games. Ideally located between Camden and Belfast and also convenient for a day trip to Acadia or Boothbay.