Vacation rentals in Islesboro Island

Relaxing A-Frame w/Fire Pit in Maine Woods • Birch

Come relax in our newly constructed, 4 season modern A frame on the Blue Hill Peninsula. Located in the beautiful town of Brooksville, only 10 mins from Holbrook Island Sanctuary, 15 minute scenic drive to Blue Hill and Deer Isle/Stonington or 1 hour to Bar Harbor/Acadia National Park. Stocked with everything needed to enjoy a relaxing getaway- EV Charger too! Is the property not available when you need it? “Maple” A Frame is just next door. See separate listing for availability OR to book both.

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.

"Nestled Inn" Cottage - With Direct Water Access

Welcome to your idyllic retreat on the serene shores of Penobscot Bay! Nestled amidst picturesque scenery, our charming waterfront cottage offers the perfect blend of rustic charm and modern comfort, ensuring an unforgettable stay. Situated right on the bay - enjoy breathtaking views and direct access to the beach. The cottage is secluded enough for a peaceful retreat but central enough to enjoy many fun adventures. Book your stay with us and experience the enchanting beauty of Penobscot Bay.

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

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.

The Cabins at Currier Landing Cabin 2: Meadow

Tranquil cabin; open plan. Bedroom w/queen bed & privacy doors. Alcove w/bunkbeds. 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 the Benjamin River Harbor shore. 2 seasonal cabins; 1 studio cabin. Centrally located on the Blue Hill Peninsula near Deer Isle, the cabins offer access to outdoor activities, cultural events, restaurants & shops.

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

Exquisitely Modern Stargazing Cottage @Diagonair

Romantic and luxurious, this 2,000 square foot modern cottage nestled on 12 acres is a favorite of honeymooners and lovers of modern design * One hour to Acadia National Park & Bar Harbor; 15 minutes to shopping, hiking, swimming * Stargazing deck * 2 full baths, one with steam shower * Fully equipped kitchen with under-counter fridge/freezer * Two gas fireplaces, one indoors, one on a covered deck * Queen bed with luxurious linens and pillows * WIFI, streaming TV, grill, bar * EV charger

"The Lair" Guesthouse

"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee and tea everyday, all day! We are closed for Winter, will re-open Mid-April. Thank you.

Rocky Top Hideaway with level 2 charging station.

Feel the magic in this quiet secluded hillside retreat. Awaken your senses with the smell of the salt air, pines and an occasional whiff of coffee beans roasting all while watching the ferry go back and forth to Ilesboro. Early risers will enjoy spectacular sunrises. Experience nature without being too far off the beaten path. A private half mile walk down the driveway will end at brick sidewalks leading you to Lincolnville Beach, one of Maine's stretches of sandy shoreline.

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).

Magical Lakefront Cabin on 5 Acres-25 Mi to Acadia

Enjoy a truly immersive experience in our unique open air lakefront cabin. The expansive screen windows allow you to lounge in comfort and feel the fresh air as you experience the birds chirping, loons calling, and frogs singing at night. On chilly nights, draw the curtains and light the gas fireplace for a cozy evening you'll never forget. Relax in a hammock, hike the trails, enjoy kayaking, paddleboarding, swimming or fishing on our peaceful lake. 40 min. to Acadia