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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Top guest favorite

Home in Hampden

5 out of 5 average rating, 117 reviews

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private sanctuary where tranquility meets luxury. Our Coastal Maine Cottage home is perched on a granite ledge that disappears twice daily with the rising tide. Enjoy the pristine interior bathed in natural light, cherry floors, and gourmet kitchen. Wake to panoramic views of the Penobscot River from the owner's suite. Conveniently located 12 minutes to downtown Bangor, our retreat offers easy access to urban amenities, an international airport, and Acadia! IG @cozycottageinmaine.

Guest favorite

The rustic cottage features a charming wooden exterior with a sloped roof, surrounded by lush greenery and colorful flowers. Large windows allow natural light to fill the space. The entryway leads to a welcoming atmosphere, complemented by ample outdoor seating nearby.

Cottage in Gouldsboro

4.93 out of 5 average rating, 212 reviews

The Cottage

A rustic cottage in the middle of Darthia Farm. The farm sits along the shore of West Bay and a short walking trail brings you from the cottage to the salt water. We grow organic mixed vegetables, herbs and flowers, raise sheep, ducks, chickens, pigs, and work with Haflinger horses. We have a farm store that is open everyday except Tuesdays and Sundays. The property is 15 minutes away from the Schoodic Section of Acadia and is surronded is by countless hiking trails and access to fresh water.

Top guest favorite

An inviting living space features a comfortable gray sofa adorned with decorative pillows. A vibrant blue wall is showcased alongside natural wood tones. A wooden coffee table sits atop a textured rug, accented by a green plant. The staircase leads to the lofted area.

Cabin in Machiasport

4.99 out of 5 average rating, 129 reviews

A-Frame, Hot Tub, Firepit, Oceanfront, Pets

Welcome to your coastal escape! Nestled in nature our cozy and unique A-frame retreat is a haven offering, seclusion, privacy and peaceful views of the ocean. Step into our stylish sanctuary where every detail whispers comfort and charm. Overlooking Little Kennebec Bay Bask in tranquility and enjoy panoramic views of the Little Kennebec Bay from your private deck. ✲ Private Hot Tub! ✲ Outdoor Fire pit! ✲ King Bed! ✲ Abundant hiking! ✲ Wood Burning Indoor Fireplace! ✲ Local Kayaking! ✲ Grill

Guest favorite

A newly renovated cottage is nestled among dense green trees on a granite cliff, overlooking calm waters. The red exterior of the house stands out against the natural surroundings, with large windows allowing ample light. A serene and tranquil atmosphere is created by the lush landscape.

Cottage in Southwest Harbor

4.97 out of 5 average rating, 149 reviews

Southwest Harbor Cottage

Enjoy unparalleled views of bustling Southwest Harbor and the beauty of Acadia National Park from the comfort of Eagle's Nest. Perched on a granite cliff, this thoughtfully designed little home provides for your every need. For anything else, take the ten minute stroll into the village, where you'll find plenty of local shops and restaurants. You can access the water via a set of stairs leading from the property to the shoreline. End your days on the deck and keep your eyes peeled for seals!

Top guest favorite

Home in Lamoine

4.97 out of 5 average rating, 103 reviews

Timber Point – Secluded Waterfront Oasis

Timber Point has beautiful coastal views and water access in a modern air conditioned 4-Bedroom+2-Bath home. Gorgeous water views from every room. Ideally located minutes from Acadia National Park. Walk to Lamoine Beach or launch your boat at nearby Lamoine State Park. This secluded home has private access to an unspoiled coast with wonderful views of Racoon Cove. Explore all the beauty of Acadia National Park, kayak the sheltered cove, or just watch the birds and tides from your patio!

Top guest favorite

A cozy porch is featured at the entrance, highlighted by rustic wooden beams and comfortable seating. Surrounding greenery and distant crops create a serene countryside backdrop, enhancing the peaceful setting of the cottage.

Cottage in Trenton

4.99 out of 5 average rating, 661 reviews

Whitetail by the River, Acadia National Park 10m

Whitetail Cottage - 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Tiny home with WIFI is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature. Enjoy a stroll to the water, privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 & cozy for 4. Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

Top guest favorite

The image captures the rocky shoreline at sunset, with vibrant shades of purple and orange reflected on the water's surface. To the right, the cabin's A-frame design is highlighted, featuring large windows that offer a view of the surrounding trees.

Cabin in Steuben

4.97 out of 5 average rating, 207 reviews

*Stunning Views* Oceanfront Chalet

Oceanfront cabin perched on the edge of Dyer Bay surrounded by large cedar and spruce trees. A perfect retreat nestled in a quiet, private neighborhood off the beaten path. This is where you get away from it all, and enjoy proximity to all the best of Downeast. The view is spectacular, and wildlife abounds. Watch the lobster boats work their traps just in front of the house. Not appropriate for small children. Sorry, NO PETS , we're allergic :-(

Top guest favorite

An aerial view of a single-story waterfront home is presented, showcasing a gray exterior with a sloped roof. A paved driveway leads to a two-car garage on the right. The surrounding landscape consists of green grass and trees, with a serene body of water visible in the background.

Home in Ellsworth

4.98 out of 5 average rating, 100 reviews

Graham Lakeview Retreat

Escape to the beauty of coastal Maine in this peaceful and fully-equipped waterfront home—just 40 minutes from Acadia National Park. Enjoy serene water views, launch one of the provided kayaks, or soak in the jacuzzi tub after a day of hiking. Ideal for couples, families, solo travelers, and your four-legged friends, too! Whether you're here for the national park, the coast, or just a quiet escape, this welcoming retreat has everything you need.

Top guest favorite

A modern tiny house features large glass doors opening to a spacious wooden deck. Adirondack chairs are placed near a table under a black umbrella, surrounded by flower pots filled with colorful blooms. Lush greenery is visible in the background, framed by a partly cloudy sky.

Tiny home in Trenton

5 out of 5 average rating, 197 reviews

The Tiny House with the Enormous View of Acadia

The Tiny House on Goose Cove is the perfect place from which to enjoy your visit to Acadia National Park. Set on three acres of shore front property, the house features spectacular views of Mount Desert Island. The entrance to the Park, and the shops and restaurants of Bar Harbor, are just 20-25 minutes away by car. And when you've had enough of the bustle and crowds, you can retreat to the peace and serenity of this beautiful property.

Top guest favorite

A newly renovated log home is framed by tall trees, showcasing a stone base and wooden structure. Large windows adorn the front, allowing natural light to fill the interior. A spacious deck is supported by sturdy logs, creating an inviting outdoor space.

Chalet in Gouldsboro

4.93 out of 5 average rating, 326 reviews

Great Timbers Retreat Minutes from Schoodic Park

This private newly renovated log home is nestled right next to the ocean front. Radiant floors with all new appliances and granite countertops. Spa showers in both bathrooms. One large bedroom with king bed and two Queen luxury futon beds for guest. Stone fireplace. Brand new washer and dryer. Charcoal grill outside and picnic table with ocean views. Pet Friendly there are pet beds and crate available

Top guest favorite

A view from above captures the cottage set amidst a grassy area, surrounded by trees. In the background, the ocean extends towards the horizon, with hints of shoreline visible. The structure is positioned to showcase its proximity to nature.

Cottage in Lamoine

4.97 out of 5 average rating, 117 reviews

Meadow Point Cottage

Meadow Point cottage is located on a very quiet five acre property with panoramic views of Frenchman's Bay and Mount Desert Island. It takes about thirty minutes to drive over to MDI and Acadia National Park. The property has a private beach for kayaking and woods with a picnic area and fire pit. It is a wonderful spot for walking and viewing wildlife; ducks, eagles, shore birds, seals and deer.

Top guest favorite

Cottage in Waltham

4.95 out of 5 average rating, 827 reviews

Quiet lakefront cottage on Graham Lake

Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets