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 ﺩ.ﺇ 184 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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Top guest favorite
A rustic fire pit area features four blue Adirondack chairs arranged around a stone circle, set within a grassy space. A small table sits nearby, and a serene tidal cove is visible through the trees in the background.
Camper/RV in Sorrento
4.91 out of 5 average rating, 134 reviews

Long Cove Hideaway

Newly upgraded to 2018 RV! Escape the tourist madness of Bar Harbor at your own private tidal cove. Camp with the comforts of home, water, power and Wifi. Outdoor grill, awning and lobster cooker for the complete Maine experience. After a hard day of hiking relax by fire pit. The Schoodic National Scenic Byway is on the far side of Long Cove, and you can hear some traffic noise from outside the RV, but for complete silence check out my other two places by looking at "about me" on my profile.

Top 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, 214 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
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, 100 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.

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
4.97 out of 5 average rating, 226 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 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, 210 reviews

*Stunning Views* Oceanfront Nordic House

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, we're allergic :-(

Guest favorite
A wooden dock extends into a calm lake, with two green chairs positioned at the edge. On one side, a red canoe is visible, while on the other, a green kayak rests alongside. Lush trees frame the scene, providing a serene setting.
Chalet in Ellsworth
4.85 out of 5 average rating, 134 reviews

Mainely Green Lake Superior Recreational Retreat

This gracious three bedroom two bathroom home is the perfect getaway to relax and experience Maine. Our home is located in a secluded area where you right away feel that you are entering a calm and peaceful place. We have tried to make our home as cozy and family friendly as possible. Cozy up by the fireplace and have a wonderful time. In the summer you can enjoy swimming in the lake, hiking, biking, fishing, outdoor bbq, outdoor fire pit and much more.

Guest favorite
A cozy waterfront home is set against a backdrop of lush greenery. A spacious deck spans across the front, leading to a circular fire pit area surrounded by Adirondack chairs, inviting relaxation and outdoor gatherings.
Home in Franklin
4.96 out of 5 average rating, 136 reviews

Waterfront near Acadia | Hot Tub| Kayaks| Bay View

Welcome to the 'Maine Squeeze'- where morning coffee tastes better on your private waterfront deck and every sunset over Hog Bay feels like a personal show just for you. Located just 40 minutes from Acadia National Park, this cozy coastal retreat offers the perfect blend of adventure and relaxation. Imagine kayaking right from your backyard, soaking in the hot tub under a canopy of stars, and falling asleep to the gentle sounds of the bay.

Top guest favorite
The log home's exterior features a large, angled window surrounded by tall trees. A wooden deck is visible, and natural stone landscaping with patches of vibrant foliage is present in the foreground, capturing the home's serene connection to the forest.
Chalet in Gouldsboro
4.94 out of 5 average rating, 347 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, 124 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
Home in Gouldsboro
4.93 out of 5 average rating, 103 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).

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, 143 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!

Top guest favorite
Cottage in Bar Harbor
4.95 out of 5 average rating, 314 reviews

The Lighthouse Cottage at Bay Meadow

At the foothills of Acadia National Park and in the seaside village of Salisbury Cove, Bay Meadow Cottages offers comfort and convenience. Stay with us and be amongst the adventurous and the young at heart. 5 min to Acadia National Park, 10 min to Bar Harbor.

Popular amenities for Winter Harbor waterfront rentals