House holiday rentals in Winter Harbor

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Top-rated house rentals in Winter Harbor

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Guest favourite
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
4.79 out of 5 average rating, 101 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 favourite
A charming pathway made of stone meanders through lush greenery, leading to a yellow cottage. The entrance is framed by vibrant flower pots and a welcoming garden, creating a serene atmosphere that invites exploration.
Home in Bar Harbor
5 out of 5 average rating, 113 reviews

In town retreat close to Acadia

This cozy one bedroom retreat is ideally located for walking to downtown or a stroll into Acadia. Secluded off of a residential street and with off street parking, the house has a private courtyard for you to enjoy, a full kitchen, washer/dryer and AC/heat. The park's loop road with access to Sand Beach, Ocean Drive, Champlain mountain and a huge network of trails are just down the street while restaurants, the village green, shops, shore path and an active waterfront are a 15 min. walk away.

Guest favourite
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
4.93 out of 5 average rating, 181 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.

Top guest favourite
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
4.95 out of 5 average rating, 240 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 favourite
A single-story red house is surrounded by greenery, featuring a welcoming deck with outdoor seating. Flanking the entrance are two neatly trimmed shrubs, and a small garden bed is visible in the foreground. The natural setting conveys a sense of tranquility.
Home in Lamoine
4.82 out of 5 average rating, 114 reviews

Quiet 2-bedroom house on Acadia's doorstep.

Minutes from Acadia, Bar Harbor, Ellsworth and other DownEast destinations. Relax with the whole family at this peaceful home in the heart of Vacationland. We are nearing the end of a long renovation, so you will find some projects unfinished (mostly exterior). But, we hope that won't stop you from having a great time exploring the area. New floors, kitchen, lighting, and hot water heat pump - we've poured a lot of love and energy into making this a great spot for our family, and yours!

Top guest favourite
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, 297 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.

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, 150 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!

Guest favourite
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
4.9 out of 5 average rating, 124 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.

Top guest favourite
The open-plan kitchen and living area feature sleek wooden cabinetry and luxury appliances. Bright natural light filters through large windows that frame the peaceful outdoor surroundings. A dining table accommodates four, while the cozy seating area invites relaxation amidst the modern furnishings.
Home in Lamoine
4.92 out of 5 average rating, 168 reviews

Lamoine Modern

This modern house designed by award-winning architect Bruce Norelius and built by Peacock Builders is located in the woods of Lamoine but close to Bar Harbor and Acadia National Park for day and night excursions. Furnished with luxury appliances and supplies for your comfort and use, it is a short walk to quiet Lamoine Beach with views of Mount Desert Island and Frenchman Bay. Peaceful, modern retreat. Please, no pets. Family-friendly with the gear needed for the littlest guests.

Top guest favourite
A charming cottage exterior is displayed, featuring traditional shingled siding and a light blue front door. Two gable dormers top the structure, while flower planters with colorful blooms line the entryway, complemented by clear blue skies overhead.
Home in Bar Harbor
4.99 out of 5 average rating, 206 reviews

Hulls Cove Cottage

Settled right outside Hulls Cove Village and its entrance to Acadia National Park, this lovely, cozy cottage is minutes from downtown Bar Harbor and its shopping, restaurants, kayaking and other activities. A classic New England shingled cape, you'll feel right at home in the updated living space, with an upstairs queen bedroom, loft with twin beds, and private backyard. Centrally located to take advantage of everything Mt. Desert Island has to offer! Registration #VR1R25-047

Top guest favourite
An open living area features a casual seating arrangement with a red accent chair and a blue armchair. A light-colored table sits nearby, complemented by a decorative rug with a lobster design. The kitchen area, equipped with modern appliances, is visible in the background.
Home in Bar Harbor
4.94 out of 5 average rating, 251 reviews

Hulls Cove Hideaway.

Located about a 1/4 from groomed X-country ski trails. Thank you for considering the Hideaway for you stay. The house is well equipped for your comfort. Located near the Hulls Cove park entrance and beach. The calendar does reflect availability, please believe the calendar, if it won't let you book the dates you are looking for that does mean it is not available. We are dog friendly, however we do not accept cats for allergic reasons.

Top guest favourite
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, 121 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 house rentals in Winter Harbor

Quick stats about house rentals in Winter Harbor

  • Total holiday rentals

    Explore 60 holiday rentals in Winter Harbor

  • Nightly prices starting at

    Winter Harbor holiday rentals start at $189 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,170 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Winter Harbor holiday 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!

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