Family-friendly holiday rentals in Islesboro

Relaxing and cozy A-Frame, 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.

Hobb’s House - Year Round Log Cabin on the Water

Cozy 2 Beds, 1 pullout sofa bed, 2 Bedroom, 2 Bath Log Cabin with water/mountain views on Hobb’s Pond. Relax on the dock, grill from the deck, canoe (1)/kayaks (2)/swim during the day and relax with your streaming services on the smart TV at night. 5min drive to the Camden Snow Bowl for ski/snowboard during the winter. Ice skate on the pond. Rent out a boat during your stay. 13 min drive to downtown Camden for great restaurants and a sunset cruise on a sailboat. Close proximity to hiking trails!

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.

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.

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.

"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.

Nebi—Private Yacht on Scenic Damariscotta River

With warm wood interior, Nebi has the comfort of a home and a 360-degree view of the tidal Damariscotta River. Experience a unique Maine adventure, swim right off the boat, or paddle the inclusive kayaks downriver to view everything from seals to ospreys and oyster farms. The quaint twin villages of Damariscotta - Newcastle are a 2-minute stroll away from the private marina with charming restaurants, galleries and a short drive to gorgeous lighthouses, walking trails and beaches.

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private 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.

Forest Cabin with Wall of Windows

Escape to our newly built 850 sq ft cabin in Midcoast Maine, a peaceful retreat nestled in a 30-acre forest. Perfect for up to 6 guests, this unique space features a stunning wall of windows with forest views, just a short drive from charming coastal towns and scenic parks. Wake up to the gentle morning sun cresting over the trees, relax and breathe deeper under a star-filled sky, and witness what all four seasons have to offer. Your serene getaway awaits!

Belfast Ocean Front Cottage

This quaint ocean front cottage is surrounded by lovely flower gardens and a panoramic view of Belfast Harbor. You're 20 feet from the beach ,and a 10 min walk to town.We have recreational kayaks you can use to paddle about the bay and up the river. With a shabby-chic decor, lots of windows & light, the cottage will steal your heart & give you a Maine experience to remember!