Cottage holiday rentals in Islesboro

Cottage by the River 10mi to Acadia: Fireplace+Pit

Whitetail by the River- 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Tiny home with WIFI is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature. Enjoy a stroll to the water, privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 &cozy for more Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

Beachfront Guest Cottage - Year-round Hot Tub!

Our cozy guest cottage has easy beachfront/kayak/canoe access (if you bring your own) and is located very close (within walking distance at low tide) to the public boat launch for larger boats. Great location to explore Deer Isle, Acadia (approx 1hr), Castine (45m), and the Bangor (1hr) area. Brave children and adults even swim from the beach but comfortable swimming ponds/lakes are 10m in several directions. The hot-tub is open year-round! Additional guests can be considered prior to booking.

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.

Private Waterfront Home with Kayaks and Firepit

Retreat to your own coastal oceanfront paradise, where each day begins with breathtaking views. A private boardwalk leads to your secluded beach — perfect for morning strolls, exploring tidal pools, or launching kayaks into sparkling waters. Evenings bring fireside marshmallows under the stars with waves as your soundtrack. Whether you seek adventure with scenic drives to Acadia National Park or quiet mornings with coffee, sea breezes, and seabirds, this is where comfort meets Maine’s coast.

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.

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.

Cottages at Oakland Seashore (Cottage #8)

Nestled on 70 acres of oceanfront property in Rockport, Maine, the cottages at Oakland Seashore are the perfect choice for a romantic getaway, vacation with friends, or a family gathering. Formerly the Oakland Seashore Motel & Cabins, I recently purchased the property and have decided to rent a few of the cottages this summer and fall on a weekly basis. Reminiscent of a bygone era, these cottages are simple and provisioned with the basics, but have the most remarkable ocean views.

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).

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

The Ferrykeeper’s Cottage is a light filled oasis, surrounded by water, meadows & views of the famous Eggemoggin Reach. Our cottage offers handcrafted counters, stone sinks, & oceanic tile to create a unique setting. 3 houses to the beach. Borrow a kayak & explore our shore. Property borders Scott’s Landing - a treasure trove of birds, sand dollars, porpoises, seals & a family of foxes. *Queen bed + flip down sofa (latter suitable for 1 adult OR 2 small kids)

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Owl Glass Cottage

Breathtaking oceanfront private cottage. Hinged staircase to second floor sleeping loft. French doors open to wrap-around patio and lawn that slopes to Ocean. 180 degrees of views. Perfect spot for relaxing or having a campfire in the evening. Enjoy your morning tea or coffee watching lobster and sailboats or kayakers explore and wander.