Holiday houses in Winter Harbor

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Quick stats about holiday rentals in Winter Harbor

  • Total holiday rentals

    Explore 130 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 4,260 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    130 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!

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, 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 favourite
Loft in Gouldsboro
5.0 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.

Superhost
Tiny home in Gouldsboro
4.9 out of 5 average rating, 21 reviews

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

Reconnect with nature, where peaceful waterfront views and coastal Maine's beauty invite you to slow down and recharge. Explore nearby trails, enjoy quiet mornings by the bay, and gather around the fire under the stars. Wi-Fi is available for light use, making it easy to unplug and embrace the outdoors. ➤ Firepit w/ Built-in Grill Grate ➤ Waterfront Views ➤ Outdoor Seating & Grill Whether you're seeking fresh ocean air or a peaceful escape, this is the perfect place to reconnect with nature.

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, 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
5.0 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 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
4.89 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 favourite
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 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
5.0 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.

Guest favourite
Home in Gouldsboro
5.0 out of 5 average rating, 15 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
Apartment in Winter Harbor
5.0 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 favourite
The exterior of a charming house is visible, featuring a sloped roof and weathered wooden siding. Decorative elements include American flags and potted plants. A staircase leads to the entrance, surrounded by landscaped gardens and greenery.
Home in Gouldsboro
4.88 out of 5 average rating, 137 reviews

Home away from Home

Nestled in a quiet location! Screened in balcony to enjoy the view! Cleared path to the oceanfront to enjoy sun bathing or sea glass hunting Not far from Schoodic Acadis National Park which offers some serene hiking and biking paths Two ferries located in Winter Harbor to go exploring in Bar Harbor There are several fantastic Restaurants I have left plenty of local information at the property

Guest favourite
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
4.88 out of 5 average rating, 34 reviews

Downtown Coastal View Apartment w/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.

Popular amenities for Winter Harbor holiday rentals

When is the best time to visit Winter Harbor?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$303 NZD$303 NZD$355 NZD$353 NZD$414 NZD$457 NZD$520 NZD$476 NZD$423 NZD$431 NZD$374 NZD$345 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 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