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
4.79 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.

Superhost
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.

Guest favourite
A charming home exterior is showcased with gray siding and a welcoming front porch. Bright flower pots are placed beside the entrance, while a stone walkway leads to the door. Lush greenery surrounds the property, creating a serene outdoor setting.
Home in Winter Harbor
5 out of 5 average rating, 11 reviews

Wonderful Winter Harbor Retreat!

Relax with the whole family at this charming and peaceful home. Located in central Winter Harbor, walking distance to restaurants, shops and beautiful water views. Bike or drive the 6-mile Acadia National Forest Park loop, which is just 3 miles away. The scenic view around the park is spectacular. Great hiking. Short ferry ride to Bar Harbor, running 4-5 times daily from late May to Columbus Day. Free Island Explorer provides shuttle service in the area and all over Bar Harbor.

Top Guest favourite
A game of Connect Four is positioned on a woven placemat, set against a backdrop of large windows. The serene view displays the water of Flat Bay and surrounding trees, illuminated by golden sunlight from the setting sun.
Cottage in Milbridge
4.97 out of 5 average rating, 222 reviews

2026 Spring Waterfront! Hi-Speed Wifi on Flat Bay

Spring 2025 ~Visit Acadia Park & Bar Harbor by day & stay here at night. Our 1.4 acre shore-front family retreat began an 18 month renovation Fall of 2018 & only opened recently - Dishwasher, new beds, Hi-speed Internet no data limit. We fell in love with this quiet coastal sanctuary, the perfect place to reconnect with nature while staying on grid. ☪ At night you'll experience deafening silence under the natural light of the stars. High-speed Internet keeps you connected.

Superhost
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.

Guest favourite
Two adirondack chairs are positioned on a grassy lawn, facing a serene waterfront view. A nearby tree casts gentle shadows, while the clear blue sky and sunlight create a peaceful atmosphere. The landscape features a mix of foliage and water, inviting relaxation.
Home in Gouldsboro
5 out of 5 average rating, 12 reviews

Beachfront Cottage with Fire Pit in Watering Cove

Beachy Watering Cove Cottage, waterfront, fire pit 1 Bedroom, 2 bathroom, living room with pull out sofa and doors, sleeps 4, private beach, firepit. This stunning property has everything you may need for a romantic vacation! There is a sandy beach, gorgeous sunsets, and a fire pit for those nightly chats while stargazing under the clear Maine skies. Relax on the spacious lawn playing lawn games like you did in your childhood. Close to amenities!

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, 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 favourite
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 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, 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 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.

Top Guest favourite
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, 138 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!

Guest favourite
A cozy living area features a light-colored couch with decorative pillows, positioned near a window that allows natural light to illuminate the space. A wooden coffee table holds a bottle of wine and two glasses. The neutral walls create a calm atmosphere.
Home in Winter Harbor
4.88 out of 5 average rating, 25 reviews

The GrindStone Bungalow

Enjoy all that This Historical Home has to Offer..and the Wonderful outdoors Surrounding it. A Ferry to Bar Harbor close by. A 9 hole Golf course Est.1891 Watch the waves crash in At Schoodic Point Enjoy your morning coffee on the enclosed front porch..

Popular amenities for Winter Harbor holiday rentals

When is the best time to visit Winter Harbor?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$297 NZD$297 NZD$347 NZD$346 NZD$405 NZD$447 NZD$508 NZD$466 NZD$413 NZD$422 NZD$366 NZD$337 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 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 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 20 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 $85 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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