Holiday rentals 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, 104 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
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.

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.

Top guest favourite
The exterior of the apartment building is shown, featuring a gray shingled facade with black shutters. A picnic table is positioned in front, surrounded by greenery, along with a grill and a propane tank. Decorative signs indicate Schoodic and Winter Harbor.
Flat in Winter Harbor
4.97 out of 5 average rating, 71 reviews

Schoodic apartment

Tastefully decorated and well maintained older apartment that is located a little over a mile from the Schoodic section of Acadia National Park where you can bike or hike the trails. What you see in the pictures is what you get. We have been renting to tourists for well over twenty years now. It's not quite all-inclusive but stocked with everything we can think of that you may forgotten or need to get your vacation started. It is perfect for thrifty travelers like ourselves.

Superhost
Tiny home in Gouldsboro
4.87 out of 5 average rating, 15 reviews

Bay Front A-Frame | Near Birch & Bunker's Harbor

Escape to West Bay Acadia RV Campground in Gouldsboro, where coastal magic meets cozy simplicity. This charming tiny home and RV retreat invites you to wake to ocean-kissed mornings, take in stunning waterfront views, and unwind by the fire as stars shimmer over the bay. ➤ Private firepit with built-in grill grate ➤ Waterfront views ➤ Outdoor seating and grill area ➤ Sleeper sofa in the living room A serene Maine getaway where every sunrise feels like your own private paradise.

Top guest favourite
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, 11 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 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
4.95 out of 5 average rating, 19 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).

Guest favourite
Inside the Tree Collection Cabin, a cozy space features a queen bed adorned with a patterned blanket. The warm wooden walls create a natural ambiance, complemented by bright windows offering a view of the sunset. A welcoming green door enhances the rustic charm.
Cabin in Gouldsboro
4.85 out of 5 average rating, 13 reviews

*The Tree Collection* View|Beach

Rustic Charm Among the Trees, Steps from the Ocean Tucked into a quiet grove of evergreens on the 22-acre Bluff House Inn property, the Tree Cabins are ideal for guests craving a nature-immersed stay with proximity to Acadia’s Schoodic Peninsula. These cozy hideaways are steps away from hiking trails, pink granite shoreline, and unforgettable sunsets over Frenchman Bay.

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.

Superhost
Home in Gouldsboro
5 out of 5 average rating, 4 reviews

Waterfront Sea Cottage w/ Fire Pit, 1 dog, waterto

Waterfall Sea Cottage is a charming 2 bedroom cottage with breathtaking views from every window. Enjoy the warmth of the massive fireplace with gas logs, or relax on the spacious deck overlooking the waterfalls. Use our kayak and 2 stand up paddle boards to put in the water at high tide. Your 1 dog is ok.

Popular amenities for Winter Harbor holiday rentals

When is the best time to visit Winter Harbor?

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Avg. price£133£133£155£155£181£200£227£208£185£189£164£151
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 bed and breakfast rentals in Winter Harbor?

    Experience the best of Winter Harbor with our bed and breakfast rentals, starting at about $180 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 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 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 20 homes with air conditioning, over 30 homes with a bbq area, 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 £38 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    120 of Winter Harbor holiday rentals include wifi 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!

  1. Airbnb
  2. United States
  3. Maine
  4. Hancock County
  5. Winter Harbor