Family-friendly holiday rentals in Islesboro

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 800 Mbs fiber internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. We’re very pet friendly!

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 waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Flower Farm Loft

When you arrive at the Flower Farm Loft you're greeted by our dogs, who will likely jump on you with muddy paws and request fetch and pets. You're immediately surrounded by flowers in our gardens and flower studio. The loft has big east facing windows that look over our farm and surrounding fields. You'll open the curtains in the morning to incredible sunrises over Kilkenny Cove, and end your nights at your private fire pit with immaculate star filled skies that will make it hard to go inside.

Lovely new loft in permaculture gardens

Old Souls Farm/Linden Lane Permaculture is an urban organic farm-garden a short walk from the bustling downtown harbor of Camden, Maine. The new (2021) loft apartment is clean, comfortable, with lots of amenities, including guest wifi and laundry. The neighborhood is quiet, wooded, historic. As a guest you’ll be in the midst of our organic gardens, orchards, and meadows, and can request a site tour. Nearby: Camden State Park, Laite Beach, and famous Aldermere Farm. You’ll love staying here.

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.

The Birch Bark Cabin

Completely unplug at this silent and stunning off-the-grid cabin situated in the heart of mid coast Maine. Minutes from several lakes, ponds and Penobscot Bay. Total privacy in the woods, private fire pit, tidy composting toilet and LED lighting. Propane stove and fresh water included. Sun shower available upon request. King sized bed is made up with sheets, blanket and down comforter. Private parking and red flyer wagon provided to carry in your gear - 200 foot path to cabin.

Tiny house with AC!!

A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

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).

Little Apple Cabin on 5 acres, amazing stargazing!

Little Apple Cabin is a private tiny cabin on five wooded acres, created for guests who want quiet, space, and deep rest. Surrounded by trees and farmland, it’s a simple, intentional place to slow down, sleep well, and enjoy Maine without crowds or noise. The cabin features a king bed on the main level, a cozy wood stove, and a wrap-around cedar deck for coffee, reading, and stargazing. Camden and Rockland are about 25 minutes away, and Belfast is about 30 minutes.

Long Cove Artist Cottage

Rustic little self-contained Maine cottage on mahogany deck with outdoor shower overlooking flower gardens and Long Cove. Sweet and simple. Two rooms plus galley kitchen with eating area. Walking, swimming, and boating: everything you need in one location, the perfect retreat. Your artist hosts are available in adjacent house.