Vacation rentals in Winter Harbor

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winter Harbor

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

1 of 1 pages1 / 1
Guest favorite
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 favorite
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, 100 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 favorite
An open concept living area features vaulted wooden ceilings, with natural light illuminating the space. A sofa and armchair are positioned near a small table. Large windows adorned with patterned curtains allow light to fill the room, creating a warm and inviting environment.
Loft in Gouldsboro
5 out of 5 average rating, 76 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 favorite
Home in Winter Harbor
4.9 out of 5 average rating, 127 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 favorite
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!

Guest favorite
Home in Gouldsboro
5 out of 5 average rating, 14 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 favorite
Cottage in Gouldsboro
4.92 out of 5 average rating, 165 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, 347 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
Home in Gouldsboro
4.93 out of 5 average rating, 103 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 solarium features large windows adorned with sheer curtains, allowing natural light to fill the space. A blooming bush with purple flowers and greenery surrounds the exterior, while potted plants contribute to the serene ambiance of the outdoor area.
Apartment in Bar Harbor
4.98 out of 5 average rating, 217 reviews

Lighthouse Retreat, 200 ft from Acadia Nat'l Park!

The Lighthouse Retreat is a studio apartment with a solarium entryway, totally private. Owners quiet and upstairs. We're 200 feet from Acadia National Park. You can be off-road hiking or biking in minutes! Downtown Bar Harbor, boat tours, restaurants, shopping, a mile away. Perfect for couples, friends or anyone wanting to explore unique coast of Maine!

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.

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, 143 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. priceR 2,860 ZARR 2,860 ZARR 3,351 ZARR 3,334 ZARR 3,906 ZARR 4,315 ZARR 4,904 ZARR 4,495 ZARR 3,988 ZARR 4,070 ZARR 3,531 ZARR 3,253 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 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 30 homes with a bbq area, over 20 homes with air conditioning, over 60 homes with wifi, 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 R 817 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!

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