Holiday houses in Winter Harbor

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Top-rated holiday rentals in Winter Harbor

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

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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
4.8 out of 5 average rating, 103 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 bright living room is showcased with light blue walls. Comfortable seating is provided by a pair of sofas, accompanied by a coffee table in the center. Natural light floods through a large window, creating a welcoming atmosphere.
Home in Winter Harbor
4.97 out of 5 average rating, 39 reviews

Winter Harbor's Hidden Gem

Our home is the perfect location! We are a 1/2 mile from Acadia's Schoodic point entrance, walking distance to the Bar Harbor ferry, farmers market & multiple eateries. While here you can enjoy a large yard with day lilies, lupine, peach & plum trees & huge grape vines! The most privacy & outdoor space you will find in Winter Harbor! Enjoy the firepit or BBQ grill & play some corn hole & badminton! We'd love to accommodate you and your family to have the best vacation Winter Harbor can offer!

Top Guest favourite
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, 101 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 favourite
Loft in Gouldsboro
5 out of 5 average rating, 77 reviews

Fisherman's Nook & Schoodic Retreat

Upstairs apartment, interior & exterior stairs/ all private space. Open concept living room 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 platform bed, dresser, bedside tables, sound machine, closet, ceiling fan, window A/C. Bedroom door opens to a small private deck w/stairs to ground level.

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, 128 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 favourite
Home in Winter Harbor
4.91 out of 5 average rating, 11 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!

Top Guest favourite
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, 71 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!

Superhost
An aerial view of a charming cottage nestled near the water’s edge, surrounded by lush greenery. The blue waters reflect the sky, while trees frame the serene landscape, creating a peaceful retreat. The cottage features a sloped roof and welcoming exterior.
Home in Gouldsboro
4.88 out of 5 average rating, 32 reviews

Beautiful Oceanfront Estate

Beautiful oceanfront cottage with sweeping views of the Atlantic Ocean and steps away from Acadia National Parks renowned Schoodic Peninsula. Nestled in Birch Harbor, the Chart House offers visitors an abundance of activities from kayaking, fishing, opportunity to collect sea glass, biking, star gazing and much more. The house offers two bedrooms, plus more sleeping arrangements which provide ample room for family and friends.

Top Guest favourite
A newly renovated duplex in a serene neighborhood is displayed, featuring a light blue exterior with white trim. A well-maintained lawn and shrubs are visible in front, with a driveway leading to a detached garage. The sky appears clear and bright above the home.
Home in Winter Harbor
4.94 out of 5 average rating, 18 reviews

Schoodic Seaside Duplex

This newly renovated duplex is conveniently located in the heart of Winter Harbor in the quiet neighborhood of Ocean Heights. Guests can look forward to being a short walk away from all of Winter Harbor's own eateries, businesses, and sights to see. This listing is located near Acadia National Park’s Schoodic Point portion of the park. The Acadia National Park section on Mount Desert Island is an approximate 50 minute drive.

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
4.94 out of 5 average rating, 348 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
Home in Gouldsboro
4.93 out of 5 average rating, 104 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 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 Winter Harbor holiday rentals

When is the best time to visit Winter Harbor?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$305 NZD$305 NZD$357 NZD$356 NZD$417 NZD$460 NZD$523 NZD$479 NZD$425 NZD$434 NZD$377 NZD$347 NZD
Avg. temp-7°C-6°C-1°C6°C13°C18°C21°C20°C16°C9°C3°C-3°C

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 50 vacation rentals in Winter Harbor featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Winter Harbor has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Winter Harbor with our house rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Winter Harbor have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Harbor have wifi?

    Absolutely! We offer over 60 house rentals with wifi in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 30 house 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 House Rentals in Winter Harbor?

    Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with wifi, over 30 homes with a bbq area, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Winter Harbor

  • Total holiday rentals

    Explore 120 holiday rentals in Winter Harbor

  • Nightly prices starting at

    Winter Harbor holiday rentals start at $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Winter Harbor holiday 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!

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  4. Hancock County
  5. Winter Harbor