Waterfront vacation rentals in Winter Harbor

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Top-rated waterfront accommodations in Winter Harbor

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Top guest favourite
A serene landscape captures the transition of day to night, with the sky filled with shades of purple and pink. Smooth rocks line the water's edge, reflecting the calming colors onto the still surface of the bay. Lush greenery accents the foreground.
Cottage in Milbridge
4.97 out of 5 average rating, 117 reviews

Bayview Cottage on the Atlantic

Nestled at the head of Pigeon Hill Bay, our cottage is surrounded by 20 acres of fields, marshland, private walking paths, and a private pebble beach on the ocean with views of the Atlantic. Acadia National Park is nearby (1 hour plus) or take the ferry (20 minutes away) to BarHarbor. Acadia Park Schoodic Point is a must see (20 minutes). Enjoy our kayaks, our recommended day trips, blueberry picking, visiting white-tailed deer. For a full week stay we serve a lobster shore dinner for two.

Top guest favourite
An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.
Home in Hampden
5 out of 5 average rating, 126 reviews

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 12 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Guest favourite
A serene deck area features two wooden chairs and a small table overlooking a lush green lawn and tranquil water. The peaceful view includes trees framing the shoreline, offering a calming ambiance and connection to nature.
Home in Belfast
4.92 out of 5 average rating, 170 reviews

Belfast City Park Ocean House

Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal City of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, boasting breathtaking views of Penobscot Bay and beyond. The meticulously manicured grounds offer an ideal setting for relaxation and outdoor entertaining, with the added allure of explorations along the shoreline or tennis/pickleball courts at park/year round hot tub. No parties.

Top guest favourite
A fire pit surrounded by four chairs is positioned by the tranquil waters of Molasses Pond. The scene is framed by a grove of trees, with a dramatic sky stretching overhead, reflecting the calmness of the lake.
Home in Eastbrook
4.99 out of 5 average rating, 149 reviews

The Maine Getaway - Lakefront with Beach

If you are looking for a place to get away and relax, our house on Molasses Pond may be a good fit for you/your family. It is a hidden gem down a dirt road away from hustle and bustle. Peace and quiet is what you’ll find, along with a gorgeous view. It’s a great place for swimming, kayaking, paddle boarding, grilling, fishing, and laying on the hammock. We try to provide you with all the necessities you may need and are happy to answer any questions. We hope you enjoy it as much as we do!

Top guest favourite
Large windows frame expansive views of the serene coastal landscape, allowing natural light to fill the space. A low coffee table is positioned in front of the windows, complementing the neutral tones of the carpet and walls.
Home in Hancock
4.97 out of 5 average rating, 164 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!

Guest favourite
A rustic log cabin is surrounded by lush greenery, featuring a stone chimney and a flag displayed proudly. A pathway leads to the entrance, with vibrant flowers and neatly trimmed hedges flanking the cabin. The scenic lake is visible in the background, complemented by tall pine trees.
Cabin in Bucksport
4.91 out of 5 average rating, 105 reviews

Authentic Maine Log Cabin | Lakefront | Cozy

Cozy log cabin lake house is perfect for those seeking outdoor recreational adventures visiting Acadia National Park, a relaxing family lake trip, or a true Maine historic log cabin experience. Enjoy this unique home with a spacious waterfront in Bucksport, Maine. Relax in the shade of the tall pine trees, go fishing, or swimming in the lake. When you want to explore, the cabin’s location is perfectly convenient to Bangor, Brewer, Ellsworth, and Bar Harbor!

Top guest favourite
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
4.97 out of 5 average rating, 104 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 favourite
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 homes in Trenton
5 out of 5 average rating, 205 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 favourite
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
4.93 out of 5 average rating, 333 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 favourite
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, 121 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 favourite
Cottage in Gouldsboro
4.99 out of 5 average rating, 195 reviews

Beachfront Christmas Cottage w/ Firepit!

🌊 Welcome To Rocky Beach Cottage 🌊 Perched On Coastal Waters and Tucked Into The Woods, Our Cottage Sits On 120 Feet Of Private Shoreline For You To Explore. A True Maine Beachfront Cottage Only 20 Minutes Drive to the Quiet Side of Acadia National Park...The Schoodic Peninsula! 🎅 Ho, Ho Ho...Tis The Season 🎅 Rocky Beach Cottage Will Be Decorated For The Holidays Through December!

Top guest favourite
A vibrant sunset is reflected on the calm waters of Graham Lake, with streaks of orange, pink, and purple filling the sky. Silhouettes of distant hills and trees frame the scene, creating a serene atmosphere perfect for relaxation.
Cottage in Waltham
4.95 out of 5 average rating, 843 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

Popular amenities for Winter Harbor waterfront rentals

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 $70 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,570 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Winter Harbor vacation rentals include wifi 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!