Family-friendly vacation rentals in Castine

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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!

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Gothic Victorian Carriage House Apartment

This newly renovated carriage house was the original hayloft of the Gilkey House, a historic American Gothic Victorian built in 1879 by the renowned architect George Harding. Unique, private & luxurious, this 2 bdrm apartment is filled with designer touches. Bright & spacious living area is perfect for families & friends to gather, cook & create memories that will last a lifetime. Walk to the best restaurants and shops, the Farmer's Market, Oceanfront Harbor, trails, Front St. Shipyard & Marina.

Sunny Waterfront Home Overlooking Blueberry Field

5 acres of lawns, gardens, and meadows and a gentle rocky beach on Blue Hill's Salt Pond, a protected inlet of the Atlantic Ocean. The house faces south towards the water and overlooks a gorgeous blueberry field that turns a majestic shade of deep red in the fall. Please feel free to reach out with us for more information or to inquire about a longer term booking. The house has two bedrooms and baths on the main level and an two additional bedrooms, bathroom, and living space downstairs.

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Private oceanfront cottage- Steps to Penobscot Bay

Coastal, light and airy- this recently renovated cottage/ guest house is perfect for those seeking to explore all that Midcoast Maine has to offer. Each room offers panoramic views of spectacular Penobscot Bay. Watch for sailboats, eagles, seals and other wildlife from the deck, the Adirondack chairs, or from inside the home. Property is uniquely situated at the head of Penobscot Bay and offers stunning views of sunrise and sunset. Great amenities & comfort for guests. Perfect for couples.

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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.

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Maine cabin coast & forest Acadia Bar Harbor

Retreating or working remotely here is a dream. Inspiration by wildlife, quiet time, focus and reflection, an incredible secluded ocean beach nearby. The cottage sits off the beaten path, yet is only 2.5 miles from stunning sunsets at the back shore beach. The small bedrooms have comfortable beds with 100% cotton linens and bedding, USB chargers, hi speed WiFi. Large country kitchen is a pleasure to cook in. Adventures-Penobscot Bay, miles of hiking trails, lighthouse & historic forts

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Belfast Harbor Loft | Downtown

Come and experience the peaceful, yet vibrant, atmosphere of Belfast! This downtown loft is a great place to stay, being just two blocks away from the beach. Enjoy the morning light in the two bedrooms, both facing the harbor, while the living room offers a stunning view of Main Street. The loft is full of character, with its refurbished floors, exposed brick and rafters, large windows, and newly renovated kitchen and bathroom. Make yourself at home in a calm and inviting atmosphere.

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Sea Pearl

This is a Water Front property, unique and tranquil getaway. Newly renovated 2025, this is a perfect spot for your serious fun. Located on water in Penobscot. Bird watchers take notice, watch the eagles soar over head out your door, visit the many islands & see the Puffins, Whale watch. Lots to do kayaking, hiking and lot more! Or just relax in a stunning natural setting on the hammock under the apple trees. Just a short drive to Acadia National Park & Bar Harbor. See you soon.

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Artsy Tiny House & Cedar Sauna

Our family is excited to share our tiny house with you! Located on our artist collective farm, this is our favorite place on earth. It’s off grid, cottage core, and has a beautiful & fragrant cedar sauna. We are 27 minutes from Acadia National Park and surrounded by truly gorgeous local beaches. We offer super comfy beds, an outdoor shower, twinkle lights, summer nights filled with fireflies, bright maples in the fall, and cozy winter movie nights in a bed alcove like on a boat.

Delight<Farmhouse

Escape to Penobscot on Maine’s Blue Hill Peninsula. This 1,100-sq-ft coastal home sleeps 6 with 2 bedrooms and a sleeper sofa. Enjoy a sunny sunroom, large eat-in kitchen, BBQ, and eclectic art with warm, lived-in charm. Close to beaches, hiking, villages, and Acadia; market across the street. An older farmhouse with uneven floors and classic quirks—perfect for guests who love authentic, cozy, historic homes, not modern rentals. Experience slow coastal Maine living.

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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.

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)