Vacation rentals in Winter Harbor

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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
Home in Winter Harbor
4.79 out of 5 average rating, 102 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.

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
4.9 out of 5 average rating, 125 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 favorite
A tranquil scene depicts a winding river bordered by lush greenery alongside a cottage with a dark exterior. In the background, rocky cliffs steeply rise above a serene shoreline, showcasing the natural landscape of Acadia's Schoodic Loop, indicating opportunities for outdoor activities.
Cottage in Gouldsboro
5 out of 5 average rating, 27 reviews

Bike, hike, kayak Acadia cottage

Watersway cottage is one of just a few homes located along Acadia's lovely Schoodic Loop. Guests can rent kayaks, bikes, or go hiking by stepping out the back door. Walk or ride to bars, restaurants and art galleries. Enjoy our crowd-free corner of Acadia — or drive 5 min to the Bar Harbor ferry for a charming boat ride to Mt Desert Island. Alternatively, drive up the coast for more spectacular hiking, picturesque fishing villages, quirky shops and quintessential Maine culture.

Top 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, 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 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, 70 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
Cottage in Gouldsboro
4.91 out of 5 average rating, 163 reviews

Shore Haven - Oceanfront Home in Corea by the Sea

New gas fireplace insert of fall 2025** Peak season-weekly bookings only with arrival/departure on Sunday***. This cedar shingled cottage home boasts 1850 sq ft of living space on one level. It has open concept Kitchen/Dining/Living/Sun room with spectacular ocean views; 3 bedrooms; 2 baths; and a library/reading room with a double bed. The property is nicely landscaped with a gently sloping lawn to 240 ft. of bold oceanfront.

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, 344 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
A view from above captures the cottage set amidst a grassy area, surrounded by trees. In the background, the ocean extends towards the horizon, with hints of shoreline visible. The structure is positioned to showcase its proximity to nature.
Cottage in Lamoine
4.97 out of 5 average rating, 123 reviews

Meadow Point Cottage

Meadow Point cottage is located on a very quiet five acre property with panoramic views of Frenchman's Bay and Mount Desert Island. It takes about thirty minutes to drive over to MDI and Acadia National Park. The property has a private beach for kayaking and woods with a picnic area and fire pit. It is a wonderful spot for walking and viewing wildlife; ducks, eagles, shore birds, seals and deer.

Top guest favorite
Home in Gouldsboro
4.93 out of 5 average rating, 101 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, 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.

Guest favorite
A private balcony is visible, featuring a plastic chair positioned at the edge. The railing offers a clear view of the surrounding area, with a backdrop of trees and distant rooftops under a partly cloudy sky.
Apartment in Winter Harbor
4.87 out of 5 average rating, 30 reviews

Coastal View 1 bedroom Apartment & Private Balcony

Top level coastal view apartment in downtown Winter Harbor. One of the most conveniently located rentals in the area with the town's restaurants and grocery store all being either across the street or just a short walk away. Only 1 mile away from the Schoodic Point entrance of Acadia National Park. Please note that this apartment is on the third floor.

Top guest favorite
A seating area with four log chairs surrounds a wood-burning firepit, positioned on rocky shoreline. The tranquil water extends into the horizon, reflecting the cloudy sky. The landscape presents a blend of natural elements, inviting relaxation by the beach.
Cottage in Gouldsboro
5 out of 5 average rating, 141 reviews

320 Ft Of Private Beachfront w/ Stargaze Platform!

🌊 Welcome To Compass Point Cottage 🌊 Placed Below A Winding Driveway At The Edge Of Compass Point, Our Beachfront Cottage Rests 20 Feet From The Water's Edge...Surrounded On Two Sides By Over 320 Feet Of Private Shoreline With Views Of Petit Manan Lighthouse In The Distance!

Popular amenities for Winter Harbor vacation rentals

When is the best time to visit Winter Harbor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR2,862 ZARR2,862 ZARR3,353 ZARR3,336 ZARR3,909 ZARR4,318 ZARR4,906 ZARR4,498 ZARR3,991 ZARR4,072 ZARR3,533 ZARR3,255 ZAR
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 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 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 apartment rentals in Winter Harbor have wifi?

    Absolutely! We offer over 10 apartment 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 20 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 20 homes with air conditioning, over 60 homes with wifi, over 20 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Winter Harbor

  • Total vacation rentals

    Explore 120 vacation rentals in Winter Harbor

  • Nightly prices starting at

    Winter Harbor vacation rentals start at R818 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 4,110 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    120 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!

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