Vacation rentals in Winter Harbor

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Quick stats about vacation rentals in Winter Harbor

  • Total vacation rentals

    Explore 130 vacation rentals in Winter Harbor

  • Nightly prices starting at

    Winter Harbor vacation rentals start at €44 per night before taxes and fees

  • Verified guest reviews

    Over 4,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Winter Harbor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Winter Harbor rentals

  • 4.9 Average rating

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

Top-rated vacation rentals in Winter Harbor

Guests agree: these stays 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
4.8 out of 5 average rating, 107 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
Loft in Gouldsboro
5 out of 5 average rating, 82 reviews

Fisherman's Nook & Schoodic Retreat

Upstairs apartment, interior & exterior stairs/ all private area. Open concept space with full kitchen. Living area: sofa with ottoman, recliner, rocker, smart TV, ceiling fan & window A/C. WiFi. Bathroom: shower, vanity, flush, washer/dryer, laundry supplies, iron, toiletries, towels, and blow dryer. Bedroom: One queen size bed, dresser, bedside tables, sound machine, closet, ceiling fan, A/C. Bedroom opens to a small private deck w/stairs to ground level. Four free lobsters w/ 3 day stay.

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, 106 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.

Superhost
Home in Gouldsboro
5 out of 5 average rating, 3 reviews

*New* Wharf house w/Hot Tub, Sauna, Harbor Views

*New* to the market! Be among the first to enjoy this completely renovated waterfront retreat overlooking Prospect Harbor, Maine. Featuring 2 luxurious master suites, a hot tub, and a sauna perched above the harbor, you’ll wake to breathtaking views of the lighthouse and working lobster boats. Watch fishermen bring in the day’s catch—or buy fresh lobster right from the dock. Experience the authentic charm of coastal Maine in an unforgettable setting. 5 mins to Acadia National Park Schoodic.

Guest favorite
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
4.89 out of 5 average rating, 133 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
Home in Winter Harbor
4.93 out of 5 average rating, 14 reviews

Schoodic Peninsula, in Town, short walk to Ocean

Escape to a quiet, quaint, safe & friendly small town! This is a spacious and family-friendly condo, in a charming fishing village on the stunning Maine Coast. Winter Harbor is part of the Schoodic Peninsula Acadia (40 miles) a 1 hour drive to Bar Harbor, Acadia! This home offers the perfect base for outdoor enthusiasts and nature lovers! Enjoy the rugged coastline of Winter Harbor, by driving the Schoodic Loop Road with its entrance close to this home. Be ready for breathtaking views!

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, 12 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
A rustic wooden cabin is framed by greenery, featuring a covered front porch with steps leading up to the main entrance. The exterior displays natural wood siding and multiple windows, allowing for ample sunlight. Nearby vegetation enhances the serene setting.
Cabin in Winter Harbor
5 out of 5 average rating, 75 reviews

Schoodic Point Cabin

Warm and cozy vacation cabin built with your vacation in mind, a place having some illusion of being rustic and with all the comforts and conveniences of home. Pictures of the interior don't convey the ambiance inside. Especially in the evenings with the light from the fireplace reflecting off the vaulted ceiling. If you don't want to walk into a rental that looks like the house you just left. Then this may be the place for you!

Top guest favorite
Apartment in Winter Harbor
5 out of 5 average rating, 9 reviews

The Peaceful Puffin: Walk to Shops, Dining & Ferry

The "Peaceful Puffin Cottage" is a cozy 1BR, 1BA retreat in the heart of Winter Harbor. Enjoy quiet mornings, then walk or bike to local cafés, a brewery, or explore the Schoodic Peninsula—the peaceful, lesser-known part of Acadia National Park. This is the perfect location for those seeking an authentic Down East Maine Coast experience, this charming seaside escape offers comfort and coastal charm for a relaxing getaway.

Top guest favorite
A fishing boat is seen gently moving across calm waters, leaving a subtle wake behind. Lush greenery frames the foreground, complementing the serene ocean view. The horizon stretches into a clear sky, enhancing the peaceful coastal scene.
Tiny home in Winter Harbor
4.94 out of 5 average rating, 35 reviews

Winter Hbr Oceanside Cabin - Schoodic Point (ANP)

Our rustic, but comfortable cabin in the charming village of Winter Harbor welcomes you with an expansive open ocean view from the front windows. We like to say that it is a $10,000 cabin with a $10,000,000 dollar view! The cabin is quaint and well furnished on a private property. The view is unsurpassed and spectacular and features Mark Island Lighthouse and Acadia National Park's, Schoodic Peninsula coastline.

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, 354 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
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, 126 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 vacation rentals

When is the best time to visit Winter Harbor?

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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Winter Harbor?

    Four-legged friends are welcome in Winter Harbor. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Winter Harbor?

    Yes! Work meets play with ease at over 60 vacation rentals in Winter Harbor featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly cottage rentals in Winter Harbor?

    Winter Harbor has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Winter Harbor?

    Experience the best of Winter Harbor with our apartment rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do cottage rentals in Winter Harbor have air conditioning?

    Absolutely! We offer over 10 cottage rentals with air conditioning in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.

  • Do bed and breakfast rentals in Winter Harbor have wifi?

    Absolutely! We offer over 10 bed and breakfast rentals with wifi in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Winter Harbor have a bbq area?

    Absolutely! We offer over 10 cabin rentals with a bbq area in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Cottage Rentals in Winter Harbor?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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  3. Maine
  4. Hancock County
  5. Winter Harbor