Waterfront vacation rentals in Winter Harbor

Find and book unique waterfront rentals on Airbnb

Quick stats about waterfront rentals in Winter Harbor

  • Total vacation rentals

    Explore 40 vacation rentals in Winter Harbor

  • Nightly prices starting at

    Winter Harbor vacation rentals start at G$10,457 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,670 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Winter Harbor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Harbor rentals

  • 4.9 Average rating

    Winter Harbor stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated waterfront rentals in Winter Harbor

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

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Superhost
Home in Trenton
4.91 out of 5 average rating, 315 reviews

Acadia National Park ocean front & garden cottages

Both our houses are designed in the contemporary style. We used custom made decor and cherry tree furniture. A lot of windows, glass doors, bright and open space are inside the house. It is very quiet outside. You most likely will be alone at the beach. We share the whole sea cove with only one neighboring house. It is a pure paradise if you want to live on the beach on your own and within minutes of driving to the main local attractions. You'll be amazed of our botanical garden and landscape.

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
4.92 out of 5 average rating, 216 reviews

The Cottage

A rustic cottage in the middle of Darthia Farm. The farm sits along the shore of West Bay and a short trail brings you from the cottage to the salt water. We grow organic mixed veggies and fruit, raise sheep, ducks, chickens, pigs, and work with Haflinger horses. Our farm store that is open everyday except Tuesdays, Thursdays 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 and salt water.

Top guest favorite
Aerial view of a charming cottage surrounded by lush greenery and water. A spacious rooftop deck offers panoramic views. The landscape includes rocky cliffs and forested areas, while a winding bike path is seen in the distance, highlighting proximity to outdoor activities.
Cottage in Gouldsboro
4.97 out of 5 average rating, 104 reviews

Stylish ocean-view home on Acadia's Schoodic Loop

This stylish, former 1940s schoolhouse is one of just a few homes located along Acadia's scenic Schoodic Loop; guests can virtually hike or bike by stepping out the back door. Enjoy our crowd-free corner of Acadia or drive 7 min to the ferry for a charming boat ride to Bar Harbor. Alternatively, head up the coast for more hikes, picturesque fishing villages, quirky shops and quintessential Maine culture. At home, enjoy books, original art, a curated record collection and fresh local lobster.

Guest favorite
A fire pit area is surrounded by four Adirondack-style chairs, set on a grassy patch. Views of the harbor and surrounding trees provide a tranquil backdrop, with the cottage’s red exterior visible in the corner of the image. The scene captures a peaceful outdoor gathering space.
Cottage in Southwest Harbor
4.97 out of 5 average rating, 156 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
A game of Connect Four is positioned on a woven placemat, set against a backdrop of large windows. The serene view displays the water of Flat Bay and surrounding trees, illuminated by golden sunlight from the setting sun.
Cottage in Milbridge
4.96 out of 5 average rating, 231 reviews

2026 Summer Waterfront! Hi-Speed Wifi on Flat Bay

Summer 2026 ~Visit Acadia Park & Bar Harbor by day & stay here at night. Our 1.4 acre shore-front family retreat began an 18 month renovation Fall of 2018 & only opened recently - Dishwasher, new beds, Hi-speed Internet no data limit. We fell in love with this quiet coastal sanctuary, the perfect place to reconnect with nature while staying on grid. ☪ At night you'll experience deafening silence under the natural light of the stars. High-speed Internet keeps you connected.

Top guest favorite
The exterior of The Boathouse is showcased, featuring a light-colored building with green trim. The structure sits close to the water's edge, surrounded by a well-maintained lawn and a few trees. In the background, the serene bay extends towards a line of distant homes.
Home in Winter Harbor
5 out of 5 average rating, 11 reviews

The Boathouse on the ocean

The Boathouse is steps from the ocean. Relax to the sounds and smell of the sea. Watch lobster boats hauling their traps and returning with their catch. Views of Acadia National Park and Mark Island Lighthouse. A true Maine Experience. Walk to the quaint village of Winter Harbor with shops and restaurants. If hiking and biking are your thing, there are trails in the Schoodic section of Acadia National Park. Or just kick back on the sofa and enjoy the views.

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, 212 reviews

*Stunning Views* Oceanfront Nordic Cabin

Oceanfront Nordic 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.

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, 127 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
The exterior of a charming house is visible, featuring a sloped roof and weathered wooden siding. Decorative elements include American flags and potted plants. A staircase leads to the entrance, surrounded by landscaped gardens and greenery.
Home in Gouldsboro
4.88 out of 5 average rating, 136 reviews

Home away from Home

Nestled in a quiet location! Screened in balcony to enjoy the view! Cleared path to the oceanfront to enjoy sun bathing or sea glass hunting Not far from Schoodic Acadis National Park which offers some serene hiking and biking paths Two ferries located in Winter Harbor to go exploring in Bar Harbor There are several fantastic Restaurants I have left plenty of local information at the property

Top guest favorite
Home in Gouldsboro
4.93 out of 5 average rating, 104 reviews

Acadia’s Schoodic Oceanfront Cabin

Enjoy your morning coffee or dinner on the oceanside deck while waves splash underfoot. This home is situated at the mouth of prospect harbor. It’s deck overlooks open ocean with deep water frontage. Take the local ferry to MDI to explore Bar harbor’s restaurants and shops, or stay local and enjoy the less traveled side of Acadia National Park, Schoodic Pennisula (5-10 minute drive).

Guest favorite
A serene coastal view is captured, featuring several boats gently bobbing in calm waters. Lush green trees outline the shoreline, while a cloudy sky hangs over the tranquil scene, creating a peaceful atmosphere at the water's edge.
Cottage in Gouldsboro
4.84 out of 5 average rating, 37 reviews

Sleep next to the ocean in Gouldsboro!

Stay where the ocean will sing you to sleep! This unique 1920's 2 bedroom 1 1/2 bath with a small kitchenette is the perfect place to stay while you enjoy what the Schoodic Peninsula has to offer! We have lots of hiking, biking and kayaking to offer on the Schoodic Peninsula! We also have lots of places to eat including a family friendly restaurant right on site!

Top guest favorite
A seating area with four log chairs surrounds a wood-burning firepit, positioned on rocky shoreline. The tranquil water extends into the horizon, reflecting the cloudy sky. The landscape presents a blend of natural elements, inviting relaxation by the beach.
Cottage in Gouldsboro
5 out of 5 average rating, 147 reviews

320 Ft Of Private Beachfront w/ Stargaze Platform!

🌊 Welcome To Compass Point Cottage 🌊 Placed Below A Winding Driveway At The Edge Of Compass Point, Our Beachfront Cottage Rests 20 Feet From The Water's Edge...Surrounded On Two Sides By Over 320 Feet Of Private Shoreline With Views Of Petit Manan Lighthouse In The Distance!

Popular amenities for Winter Harbor waterfront rentals