Waterfront vacation rentals in Winter Harbor

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Winter Harbor

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Northport

4.83 out of 5 average rating, 12 reviews

"Nestled Inn" Cottage - With Direct Water Access

Welcome to your idyllic retreat on the serene shores of Penobscot Bay! Nestled amidst picturesque scenery, our charming waterfront cottage offers the perfect blend of rustic charm and modern comfort, ensuring an unforgettable stay. Situated right on the bay - enjoy breathtaking views and direct access to the beach. The cottage is secluded enough for a peaceful retreat but central enough to enjoy many fun adventures. Book your stay with us and experience the enchanting beauty of Penobscot Bay.

Guest favorite

A serene waterfront view features calm waters reflecting the sky, with boats docked along the shoreline. Trees in autumn hues frame the scene, while a pathway winds through the park, leading towards the water and inviting outdoor activities.

Apartment in Belfast

4.86 out of 5 average rating, 105 reviews

Downtown waterfront Belfast with amazing views.

Brand new roomy apartment on downtown Belfast waterfront. This full second floor apartment is steps from the water with sweeping views of Penobscot Bay. Apartment has wooden floors, full kitchen, living room, dining room, bedroom, and bath. Private staircase leads to your oasis across from public park and 3 mile walk trail. Venture downstairs where breakfast and lunch is available at Crumbs Provisions. Bike rentals and Saturday farmers market are within a two minute walk. Non smoking property.

Guest favorite

Guest suite in Orrington

4.97 out of 5 average rating, 110 reviews

Lake front luxury retreat with an Island View

Indulge in lakeside luxury at our modern, waterfront studio retreat! Perched on the water's edge, this pet-friendly haven offers: Private dock and lake access · Spa-inspired indoor and outdoor showers · Cozy fire pit for a relaxing movie night under the stars · Unbeatable views and direct access to the lake for swimming & soaking up the sun · The serene sounds of loons and unforgettable memories to cherish. A short drive from town, experience the best of Maine living in style and tranquility.

Guest favorite

A small balcony is seen with two metal chairs positioned to enjoy views of the harbor. The sliding glass doors offer an unobstructed view of the water, boats, and beach, with sunlight illuminating the wooden deck.

Cottage in Southwest Harbor

4.93 out of 5 average rating, 29 reviews

The Weir on the Harbor

Enjoy your beach front vacation in a newly renovated small, cozy cottage over looking a working harbor. This unique property is a short walk to many shops and restaurants. Have fun looking for sea glass and other treasures from the ocean on our semi private beach. The first floor has a modern kitchen, a living room with sleeper sofa, and full bath. Enjoy your meals on the front deck while listening to the seagulls. The second floor is a loft bedroom with small balcony overlooking the harbor.

Superhost

The restored building is positioned near the water's edge, featuring a weathered wooden facade. Large windows reflect the blue sky and provide a view of the surrounding rocks and marina. The tranquil harbor is visible in the foreground, enhancing the peaceful setting.

Apartment in Southwest Harbor

4.91 out of 5 average rating, 149 reviews

On the water. Walk to Southwest Harbor

If you want to be near the action of an active and interesting harbor, this is the place for you. You will have a front row seat to spectacular morning sunrises over the harbor, the comings and goings of the fishermen and the many boats docked at the marina and anchored in the harbor. This spacious four bedroom two and a half bath home is located at the Great Harbor Marina just half a mile from downtown Southwest Harbor. Walk to restaurants, art galleries, specialty shops and more.

Top guest favorite

A coastal cottage is shown beside a rocky shoreline, surrounded by trees. The clear blue water reflects the sky, while the cottage features a large furnished deck that overlooks the serene landscape. The environment suggests a tranquil seaside retreat.

Home in Hancock

4.97 out of 5 average rating, 149 reviews

Water's Edge-Oceanfront with Stellar View

Water’s Edge offers panoramic coastal water views in a 2-Bedroom+Loft, 1-Bath vacation cottage located feet from the shore. Ideally located between Acadia National Park’s Schoodic Peninsula and Mt Desert Island, your serene cottage has private access to the coast with wonderful views of Frechman Bay and Cadillac Mountain. Explore all the beauty of Acadia National Park, climb local mountains, kayak the Mt Desert Narrows or just watch the tides and mountains from your private deck!

Top guest favorite

Guesthouse in Penobscot

4.97 out of 5 average rating, 212 reviews

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.

Superhost

A scenic outdoor area features a stone patio adorned with vibrant flowers. Simple white chairs are arranged to enjoy views of the harbor and boats. A metal fire pit adds a cozy touch to the space, enhancing the tranquil atmosphere by the water.

Home in Stonington

4.72 out of 5 average rating, 25 reviews

A+ on Harbor, beach, patio, kayaks, walk to town

Old charm in this beautiful historic (1910) home on Stonington Harbor w/ stunning views over Maine's largest lobstering fleet & island vista. Warm & inviting, light-filled interiors - well supplied. Enjoy wrap-around deck, expansive stone patio with fire pit, small beach, 6+ kayaks & gear in areas most prime kayaking waters, plus only a 2 minute walk to the downtown shops, restaurants, theater, museum - along w/ many Deer Isle, Blue Hill, Castine, Bar Harbor attractions nearby.

Guest favorite

An outdoor deck offers a view of the river surrounded by trees. Sunlight casts gentle shadows on the wooden deck, highlighting its natural grain. Calm water reflects the greenery, creating a serene atmosphere. A paved area is visible nearby, providing additional outdoor space.

Guesthouse in Ellsworth

4.85 out of 5 average rating, 114 reviews

Large adorable 1 bedroom loft with ocean frontage

What you will love - Modern living space - Ocean Access - Frontage on Union River - Close to everything - but seems like you are in the woods. - Abundant wildlife - Store within walking distance - Outdoor deck on river - Views of Ellsworth Harbor - Full kitchen and laundry - Full bath and Half bath for guests - Air conditioning - Upscale Contemporary Decor - Situated on a 10 acre lot, with large lawn, pond, and within a 2 minute drive to downtown Ellsworth Maine.

Top guest favorite

Large windows frame a scenic view of the waterfront, with the ocean visible in the distance. The window area is adorned with a colorful valance, adding a touch of charm. Natural light floods the room, creating a bright and airy atmosphere.

Apartment in Tremont

5 out of 5 average rating, 164 reviews

Duck Cove Apartment

Enjoy salty sea air when you stay at this vacation rental apartment in Bernard, Maine! Bring along your own kayaks to take advantage of the waterfront property. Just a few miles from Acadia National Park and a 20-minute drive to Bar Harbor , the space allows you and your favorite travel companions to explore the beautiful surroundings with ease! It doesn't get any better than beautiful ocean views, direct water access, and the best lobster in the country;

Superhost

Home in Milbridge

5 out of 5 average rating, 3 reviews

New 2023 Waterfront Home near Acadia with Hot Tub

Our tidal oceanfront house rental is perfect for a memorable Maine vacation . Secluded coastal setting on a private island allows you to relax in this brand new construction. Sleeps 8 people so invite family or friends! Enjoy the tidal waters, fire-pit and outside grilling. Large deck to relax on and listen to nature’s sounds. Enjoy hiking, puffin tours and small town events. Take a trip to Schoodic Point or Acadia National Park.

Top guest favorite

A spacious waterfront apartment is depicted from the exterior, featuring a modern design with large windows that reflect the sky. A covered deck is accessible, surrounded by outdoor seating. The grassy area in front is interspersed with large stones, creating a natural landscape.

Townhouse in Vinalhaven

5 out of 5 average rating, 30 reviews

Island Getaway

Loaded with charm and coziness this apartment is a great place to enjoy a quiet retreat from a busy life! Lounge on the deck or in the hammock as you enjoy watching local fisherman hauling their traps while eagles, osprey and seagulls soar above. The ferry boat cruises back-and-forth daily right in front of you! Nature trails and Sunset Rock within walking distance.