House vacation rentals in Winter Harbor

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Quick stats about house rentals in Winter Harbor

  • Total vacation rentals

    Explore 70 vacation rentals in Winter Harbor

  • Nightly prices starting at

    Winter Harbor vacation rentals start at G$31,395 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,240 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 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 house rentals in Winter Harbor

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

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Guest favorite
A single-story country home is framed by lush greenery, featuring a wooden deck that leads to the entrance. The exterior showcases a dark wood siding with a stone foundation. Surrounding grassy areas create a peaceful setting.
Home in Winter Harbor
4.81 out of 5 average rating, 109 reviews

Maine Country Home Young

Take it easy at this unique and tranquil getaway. This little country home sits in town in the fishing village of Winter Harbor, Maine. Explore Schoodic Point, a part of Acadia National Park, while hiking, fishing, bicycling, kayaking, and picnicking at Frazer Point.Several area restaurants are within walking distance and serve up Maine traditional fare.Want to enjoy Bar Harbor as well? Take the ferry from the marina and experience sea life such as dolphins, seals, or a bald eagle on your trip.

Top guest favorite
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, 160 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 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Top guest favorite
The modern cabin is set against a backdrop of trees at dusk, showcasing large windows that emit a warm glow. The structure's unique angled roof adds interest, while the surrounding area features a grassy yard with outdoor seating and a path leading towards the entrance.
Home in Surry
4.85 out of 5 average rating, 597 reviews

Modern Maine Beach House

Welcome to our 1970’s modern architecture house meets rustic cabin. Nestled along the coast, this property offers breathtaking ocean walks and serene atmosphere. The house boasts an open concept layout with sunken living room. Featuring expansive windows that flood the space with natural light and invite the beauty of the outdoors in. Art lovers will appreciate our curated collection thoughtfully selected to enhance the mid-century modern design. Deeded beach access; 300 feet to the ocean

Guest favorite
A deck overlooks a spacious green lawn surrounded by trees showcasing vibrant fall foliage in shades of orange and yellow. The peaceful outdoor space is ideal for relaxation and enjoying the natural beauty of the landscape.
Home in Gouldsboro
4.92 out of 5 average rating, 192 reviews

The Adventure House

The Adventure House was named by a family of houseguests with 3 fun and lively children who filled their time here with adventures at Acadia National Park and beyond! We are 10 minutes from the quiet side of the park and just under an hour to the busy side, both filled with scenic beauty! We have an added amenity for families traveling with extra family or friends. We're now offering a beautiful camper that comfortably sleeps 6 on the property available only for an extra charge after booking.

Guest favorite
An open living area features large glass doors that allow natural light to flood the space. A unique wooden table with high chairs is positioned next to a modern kitchen, while a cozy seating area includes a chair and decorative accents against a backdrop of greenery.
Home in Gouldsboro
4.94 out of 5 average rating, 260 reviews

Schoodic Loft Cabin "The Roost" with Kayaks

This playful cabin offers a unique spot to unwind and explore the Schoodic peninsula and Downeast Maine. Kayaks are provided to explore island studded 462 acre Jones pond, a 10 minute walk down a trail. A 10 minute drives brings you to the less visited Schoodic section of Acadia NP, where a network of hiking and biking trails lace the coastal forests and dramatic rocky coast. Nearby Winter Harbor has shops and restaurants and even a ferry across the bay to Bar Harbor and Mount Desert Island.

Guest favorite
Home in Stonington
4.93 out of 5 average rating, 120 reviews

Bayview House 1br 2ba Stunning Harbor Views

Do you crave balmy summer evenings or frosty winter days that make you feel like you've been transported back to a simpler time? Or long for days spent on the water or experiencing village life with friendly locals in charming pubs tasting local eats? Experience the simple joys of life with rustic yet modern amenities offered at this coastal 2-story home. Whether daily strolls by the water or taking in the sunset on your deck, you'll fall in love with this lovely New England destination.

Top guest favorite
The exterior of the cottage showcases a modern design with gray metal siding and warm wooden accents. A small deck area is furnished with two chairs and a grill, surrounded by trees that provide a sense of privacy. Large windows allow natural light into the space.
Home in Mount Desert
5 out of 5 average rating, 307 reviews

The Arthaus, an eclectic retreat for two

Located on Mount Desert Islands, "Quietside". The cottage features high ceilings and an open floor plan, with a small deck looking into the woods The walls are decorated with original art work by the owner. Our location is central to the island, situated just outside the village of Somesville; 15 minutes to Bar Harbor, 10 minutes to Southwest Harbor by car. Hiking and swimming opportunities are just 5 minutes away by car. The Arthaus is not suitable for pets, despite our love for them.

Superhost
A vintage cottage is set against a bright blue sky with scattered white clouds. The house features a light yellow exterior, surrounded by a well-manicured lawn and a flowering tree. A wooden deck provides access to the entrance, adding charm to the welcoming facade.
Home in Winter Harbor
4.88 out of 5 average rating, 134 reviews

Cozy & Walkable Winter Harbor Home next to Acadia

Walk everywhere in Winter Harbor while enjoying picturesque Downeast Maine right next to the most peaceful section of Acadia National Park on the Schoodic Peninsula. This vintage cottage has everything you need to relax in a quintessential fishing village. Walk to coffee shops, restaurants, bars, a grocery store, the Bar Harbor Ferry and gorgeous harbor views. Avoid the traffic and congestion of Bar Harbor and come experience Downeast Maine's best kept secret! Sorry no dogs allowed.

Guest favorite
The kitchen features modern cabinetry in a deep blue hue, paired with light wood countertops. Open shelving displays dishware and plants, while stainless steel appliances line one side. Natural light enters through a window above the sink, complemented by decorative light fixtures.
Home in Franklin
4.97 out of 5 average rating, 116 reviews

Sunrise Over Schoodic Mountain

Located within 40 minutes of the Acadia Bar Harbor entrance this small private home offers quiet peaceful mountain views and tons of wildlife. Brand new custom built home comfortably sleeps 4. A wall of glass faces 3 mountains. Home is located 200’ from the Donnell Pond Rd and offers access to the Downeaster Rails to Trails for Atv’s. Donnell Pond offers great kayaking,boating ,swimming and fishing. Great sand beaches surrounded by the mountains you see from the house.

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, 139 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

Guest favorite
Home in Gouldsboro
4.9 out of 5 average rating, 109 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
The rustic wooden exterior of the salt box home is illuminated by the evening sun. A balcony with blue adirondack chairs overlooks a grassy area. The entrance is framed by large windows, inviting natural light into the space.
Home in Winter Harbor
4.97 out of 5 average rating, 129 reviews

Anchor Down at Schoodic Point

Anchor Down in this nautically inspired salt box home in the quaint seaside town of Winter Harbor, Maine. Comfortably furnished and well equipped for your vacation getaway. At Anchor Down you will be conveniently located across the road from the entrance to Acadia National Park's Schoodic Penninsula with hiking and biking trails and gorgeous views of the ocean.

Popular amenities for Winter Harbor house rentals