Family-friendly holiday rentals in Orland

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!

Private Lakefront Cottage Close to Bar Harbor

Newly renovated historic lakefront home on 8 acres with a lot of privacy. Conveniently located only 20 minutes from airport, this 2-story cedarshake home sits on the water's edge and is close to Bar Harbor and surrounding picturesque towns for shopping, restaurants and sightseeing. Large wrap-around porch (with dining table that seats 10 and several comfy seating areas) for family fun & outdoor dining. Large deck, perfect for swimming, lake fun and canoe rides. AC and heats in upstairs bedrooms.

The Greenhouse Cottage

We feel that the best way to describe our getaway to be “Rustic Elegance”. When you walk through the door you will instantly feel the warmth of a uniquely styled Adirondack cottage. Located nearby to the Acadia Highway (aka Route 1), we are close by to historic Fort Knox, Castine, and Acadia. Enjoy our attached “Greenhouse” which has been made over into a delightful screenhouse/patio, the country setting, blueberry fields, and the beautiful sunrises and sunsets! Fire pit, horseshoes, more!!!

Loon Sound Cottage, On the Water

Loon Sound Cottage, on beautiful Toddy Pond in Surry, is centrally located between Bar Harbor/Acadia & Blue Hill. Come and enjoy the peace and tranquility of a lakeside oasis while just being a short distance from many sites of interest. Visit nearby Castine, Blue Hill, Bar Harbor, and Acadia National Park. Hear the loons at night, kayak to beaver cove and see an eagles nest. A tranquil and peaceful setting. A perfect balance of rest and adventure. We prefer Sat-Sat. rental but flexible.

Acadia Pines Retreat HotTub-10 Min Downtown Bangor

Hot tub. Nature. Total peace. 🌲Acadia Pines Retreat-just 10 minutes from downtown Bangor and close to Acadia National Park. Warm wood ceilings, curated interiors, and cozy moments in the beautiful Maine woods. This retreat features open-concept living space styled with rich textures, soft lighting, and designer touches throughout. Sink into plush seating, enjoy slow mornings with coffee at the stone island, or unwind after exploring surrounded by stillness of forest in your private hot tub.

Waterfront-40min to Acadia-Main House-Kayaks

Lakehouse for those seeking outdoor adventures at Acadia National Park, a relaxing lake trip, or a true historic Maine cabin resort experience. Enjoy a four-season, pet-friendly, Maine lakehouse! The converted Main House at the Getogether Stays cabin micro-resort sleeps 8 and includes WiFi, kayaks, a gas grill, A/C and heat, a picnic table, and Adirondack chairs around the fire pit. The cabin is convenient to Bucksport, Ellsworth, Bangor, and Bar Harbor, making it ideal for exploring Acadia.

Lavender by the Sea

The Cottage rests over the end of Penobscot River as it opens into the Bay. The Cottage will comfortably accommodate two. The Cottage has a spacious bedroom, full kitchen, dining area, den and an all season porch with rockers. From Cottage there are views of the water and the lavender gardens. The gardens are terraced with a path down to the sea. The Carriage House Suite is available for an additional fee. it has has two bedrooms, a full bath and a sitting area. It can easily sleep four.

Hike-in off-grid Yurt on top of Maine Mt. w/Kayaks

Welcome mountain climbers, pilgrims and nature revelers! Hike-in to your fully outfitted off grid yurt and stay the night on a mountain top enjoying magnificent southerly views with a bonfire and watching the stars put on a show. Bring your sleeping bag, linens, food, and musical instruments to begin your incredible Maine adventure. The mountain is waiting, get on your way! Mountain report: blueberries are starting to ripen. Get them while they are plump and blue.

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.

Modern Cabin in the Pines • Hot Tub + Near Acadia

Enjoy our cozy home-away-from-home amid towering pines and granite boulders — the perfect respite after exploring Acadia. Our newly built cabin has rustic Maine charm and modern comforts: AC, waterfall shower, memory foam mattresses, indoor gas fireplace, outdoor gas fire pit, gas grill, hot tub, 4KTV, high-speed internet, modern kitchen, filtered water, gas range, high-end appliances, and front-loading washer/dryer.

Private Lakeside Camping in Penobscot, Maine

Private lakeside camping on Toddy pond in Penobscot, Maine 50 min. from Acadia and Bar Harbor. This 400 foot private wooded lakeside lot is available for camping. This rental is close to Acadia, Ellsworth, Bucksport and the Blue Hill Peninsula. Go out and explore the area attractions or stay put and swim, fish, and kayak on one of Downeast Maine's most popular lakes; Toddy Pond.

Field of Dreams Tiny Home

Escape to our charming tiny home near Bangor, a perfect retreat for 2. Enjoy serene field views from a panoramic window, a private hot tub, and a cozy fire pit. Inside, a modern wood-paneled interior with a projector screen for movie nights awaits. This unique stay offers tranquility and modern comfort, just minutes from the city.