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
4.79 out of 5 average rating, 101 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
A newly constructed cabin is set against a backdrop of dense forest, featuring a covered porch with wooden railings. The cabin's design includes large front doors that provide a welcoming entry. The surrounding trees create a natural and peaceful environment.
Cabin in Southwest Harbor
4.97 out of 5 average rating, 109 reviews

Cabin In The Woods: Sleepy Deer

Situated on the edge of 5 acres of forest between Acadia National Park and downtown Southwest Harbor, this cozy cabin is ideal for a weekend trip or a longer stay on beautiful Mount Desert Island. Enjoy your morning coffee on porch before heading out for a hike around Long Pond, a swim at Echo Lake, or a walk into town for the weekly Farmer’s Market, shops and restaurants - all a mile or less away! End your day around the outdoor fire pit, roasting marshmallows or enjoying an evening cocktail.

Guest favourite
A deck overlooks a spacious green lawn surrounded by trees showcasing vibrant fall foliage in shades of orange and yellow. The peaceful outdoor space is ideal for relaxation and enjoying the natural beauty of the landscape.
Home in Gouldsboro
4.93 out of 5 average rating, 181 reviews

The Adventure House

The Adventure House was named by a family of houseguests with 3 fun and lively children who filled their time here with adventures at Acadia National Park and beyond! We are 10 minutes from the quiet side of the park and just under an hour to the busy side, both filled with scenic beauty! We have an added amenity for families traveling with extra family or friends. We're now offering a beautiful camper that comfortably sleeps 6 on the property available only for an extra charge after booking.

Top guest favourite
A rustic lakefront cabin is positioned near the water's edge, featuring a spacious screened-in porch. The surrounding area includes natural stone and vibrant autumn foliage. The cabin's exterior is painted green, complemented by a wooden deck offering a view of the lake.
Cabin in Otis
4.96 out of 5 average rating, 192 reviews

Rustic Cabin on Beech Hill Pond near Acadia

Our rustic lakefront cabin is on beautiful crystal clear Beech Hill Pond near Acadia National Park and Bar Harbor, Maine. The cabin has 2 bedrooms and is suitable for 1 to 4 guests. It is furnished with the amenities listed as well as a dock, swimming float, fire pit with firewood, gas grill, and table and chairs. Enjoy the peacefulness from the screened in porch which overlooks the lake after a day of hiking in Acadia National Park. You will hear the call of the loons while relaxing.

Guest favourite
A cozy bedroom displays a spacious bed with a checkered comforter against vibrant green walls. A comfortable chair is situated nearby, and a small desk with a lamp is positioned next to the bed. Natural light streams in through a window dressed with soft curtains.
Guest house in Camden
4.93 out of 5 average rating, 120 reviews

Sleep Where The Mountains Meet The Sea

Kick back and relax in this comfortable and spacious one-bedroom guesthouse "Where the Mountains Meet the Sea". With towering trees and luscious ferns, live like a local in a quiet Camden neighborhood. Unbeatable location with lakes, rivers, and mountains all within walking distance, plus historic downtown Camden and harbor are just a 3 minute drive away. Perfect for a weekend getaway, business trip, staycation, or cozy home base while exploring everything Mid-Coast Maine has to offer.

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, 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.

Top guest favourite
Cabin in Sedgwick
4.98 out of 5 average rating, 182 reviews

Rustic Chic Private Getaway Cabin @Diagonair

Private pet-friendly Maine cabin on 12 wooded acres and blueberry fields an hour from Acadia National Park. A favorite of couples visiting Maine for the first time. • 15 minutes to shopping, hiking, swimming • Fully equipped open kitchen/sitting room with gas fireplace • Screened porch with rocking chairs and chaise • Loft bedroom with full bed and new linens • WiFi, Roku TV, gas grill, stocked bar • EV charger • Seasonal wild blueberries • Dark skies, slow mornings, quiet nights

Top guest favourite
The image captures the rocky shoreline at sunset, with vibrant shades of purple and orange reflected on the water's surface. To the right, the cabin's A-frame design is highlighted, featuring large windows that offer a view of the surrounding trees.
Cabin in Steuben
4.97 out of 5 average rating, 210 reviews

*Stunning Views* Oceanfront Chalet w/Fireplace

Oceanfront cabin perched on the edge of Dyer Bay surrounded by large cedar and spruce trees. A perfect retreat nestled in a quiet, private neighborhood off the beaten path. This is where you get away from it all, and enjoy proximity to all the best of Downeast. The view is spectacular, and wildlife abounds. Watch the lobster boats work their traps just in front of the house. Not appropriate for small children. Sorry, NO PETS , we're allergic :-(

Guest favourite
A geodesic dome is prominently situated on an elevated deck, surrounded by vibrant fall foliage. The structure showcases a wooden finish, and a small detached building is visible nearby. Clear blue skies add to the serene outdoor setting, providing a peaceful ambiance.
Dome in Ellsworth
4.98 out of 5 average rating, 218 reviews

Nomad's Rest-Secluded Modern Camp 30 miles to MDI

The modern Maine camping experience. Enjoy an unforgettable stay in a geodesic dome outfitted with detached bathroom and shower. A fantastic jumping-off point for your favorite outdoor sports with hiking and biking trails within 10 minutes of the property and 30 miles from Acadia National Park. Return from a day of exploration to views of Maine lakes, the national park and a roaring fire pit! @nomaddomehome on Insta for more pictures.

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, 342 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 scenic outdoor space features several wooden Adirondack chairs arranged around a firepit, set against a backdrop of rocky shoreline and calm coastal waters. The area is surrounded by trees, with a gentle hillside leading down to the beach.
Cottage in Gouldsboro
5 out of 5 average rating, 205 reviews

Beachfront Cottage w/ Fireplace Near Acadia

🌊 Welcome To Rocky Beach Cottage 🌊 Perched On Coastal Waters and Tucked Into The Woods, Our Cottage Sits On 120 Feet Of Private Shoreline For You To Explore. A True Maine Beachfront Cottage Only 20 Minutes Drive to the Quiet Side of Acadia National Park...The Schoodic Peninsula!

Popular amenities for Winter Harbor holiday rentals

When is the best time to visit Winter Harbor?

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Avg. price£146£156£141£153£179£198£224£206£183£186£162£149
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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 50 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 cottage rentals in Winter Harbor have wifi?

    Absolutely! We offer over 10 cottage 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 20 homes with a bbq area, over 60 homes with wifi, over 20 homes with air conditioning, 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 £37 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!

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