Family-friendly vacation rentals in Winter Harbor

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Top-rated family-friendly rentals in Winter Harbor

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
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 favorite
Tiny home in Surry
4.96 out of 5 average rating, 167 reviews

Tiny House at Wooded Bliss Homestead

On the edge of our family homestead overlooking meadow & forest, this tiny house offers a quiet, cozy refuge only 40 minutes from Acadia National Park. There's a twin daybed on the ground floor & a double futon in the loft. Full kitchen & tiny bathroom with shower too. A heat pump keeps the place toasty warm or nice and cool. The tiny house and meadow are very private on the edge of the property, and just for you. Our family's gazebo, fire pit, hammock, trail & garden are shared with guests.

Guest favorite
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 favorite
An open living area features large glass doors that allow natural light to flood the space. A unique wooden table with high chairs is positioned next to a modern kitchen, while a cozy seating area includes a chair and decorative accents against a backdrop of greenery.
Home in Gouldsboro
4.94 out of 5 average rating, 234 reviews

Schoodic Loft Cabin "The Roost" with Kayaks

This playful cabin offers a unique spot to unwind and explore the Schoodic peninsula and Downeast Maine. Kayaks are provided to explore island studded 462 acre Jones pond, a 10 minute walk down a trail. A 10 minute drives brings you to the less visited Schoodic section of Acadia NP, where a network of hiking and biking trails lace the coastal forests and dramatic rocky coast. Nearby Winter Harbor has shops and restaurants and even a ferry across the bay to Bar Harbor and Mount Desert Island.

Top guest favorite
A view from the porch showcases tall wooden posts and a ceiling with exposed beams. Bright blue skies contrast against vibrant autumn foliage, including shades of red and green in the surrounding trees, creating a serene natural setting.
Cottage in Trenton
4.96 out of 5 average rating, 423 reviews

NEW Whitetail Cottage, Acadia National Park 7m

NEW Whitetail Cottage East only 6.9 mi to Acadia National Park Maine - a hikers paradise! Centrally located for a perfect Acadia Adventure! Book for the convenient location - stay for the style. Tiny home has WIFI & SMART TV. Off the main(e) drag but nestled in a wooded property 1/2 mile from Bar Harbor Rd/Route 3 down the road from Mount Desert Island and a stones throw from multiple authentic Maine lobster pounds. Perfect for 2 . A short drive to MDI, Acadia, Bar Harbor,Southwest Harbor

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, 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 favorite
Tiny home in Lamoine
5 out of 5 average rating, 103 reviews

Artsy Tiny House & Cedar Sauna

Our family is excited to share our tiny house with you! Located on our artist collective farm, this is our favorite place on earth. It’s off grid, cottage core, and has a beautiful & fragrant cedar sauna. We are 27 minutes from Acadia National Park and surrounded by truly gorgeous local beaches. We offer super comfy beds, an outdoor shower, twinkle lights, summer nights filled with fireflies, bright maples in the fall, and cozy winter movie nights in a bed alcove like on a boat.

Top guest favorite
A cozy seating area is presented, featuring a patterned rug beneath a wooden coffee table and cushioned seating. The walls are adorned with various framed artworks, while natural light enters through a set of French doors that lead outside.
Guest suite in Mount Desert
4.95 out of 5 average rating, 308 reviews

Otter Creek Retreat hosted by Elaine & Richard

Between Bar Harbor and Seal Harbor, 10 minutes by car to both and just 5 minutes by car to the Otter Cliff entrance to Acadia Park Loop Road. Walk to the Causeway via the Grover Path in 15 minutes. 5-minute walk to the Cadillac South Ridge Trail. Large high-ceiling studio with private parking and entrance with beautiful sheltered second-story deck. We are on the Blackwoods/Bar Harbor bus route so you can catch the free Island Explorer LL Bean buses to Bar Harbor and back.

Top guest favorite
A modern tiny house features large glass doors opening to a spacious wooden deck. Adirondack chairs are placed near a table under a black umbrella, surrounded by flower pots filled with colorful blooms. Lush greenery is visible in the background, framed by a partly cloudy sky.
Tiny home in Trenton
5 out of 5 average rating, 206 reviews

The Tiny House with the Enormous View of Acadia

The Tiny House on Goose Cove is the perfect place from which to enjoy your visit to Acadia National Park. Set on three acres of shore front property, the house features spectacular views of Mount Desert Island. The entrance to the Park, and the shops and restaurants of Bar Harbor, are just 20-25 minutes away by car. And when you've had enough of the bustle and crowds, you can retreat to the peace and serenity of this beautiful property.

Top guest favorite
Cabin in Gouldsboro
4.96 out of 5 average rating, 103 reviews

Forested Cabin Decorated For The Holidays!

Wanderers | Travelers | Explorers Stained In Raven Black and Cloaked From Peering Eyes, Stonebrook Cabin Sits Proudly Concealed Behind Maine's Mighty Pines. Eclectic, Romantic and Streamside, Stonebrook Cabin Features An Expansive Sundeck Overlooking 5 Acres Of Forested Privacy and Beach Access 5 Minutes Away! 🎅 Ho, Ho Ho...Tis The Season 🎅 Stonebrook Cabin Will Be Decorated For The Holidays Through December!

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
4.93 out of 5 average rating, 334 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

Guest favorite
A vibrant sunset is reflected on the calm waters of Graham Lake, with streaks of orange, pink, and purple filling the sky. Silhouettes of distant hills and trees frame the scene, creating a serene atmosphere perfect for relaxation.
Cottage in Waltham
4.95 out of 5 average rating, 846 reviews

Quiet lakefront cottage on Graham Lake

Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets

Popular amenities for Winter Harbor family-friendly rentals

When is the best time to visit Winter Harbor?

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Avg. priceﺩ.ﺇ731ﺩ.ﺇ918ﺩ.ﺇ918ﺩ.ﺇ826ﺩ.ﺇ918ﺩ.ﺇ1,047ﺩ.ﺇ1,230ﺩ.ﺇ1,322ﺩ.ﺇ1,120ﺩ.ﺇ1,069ﺩ.ﺇ870ﺩ.ﺇ903
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Quick stats about vacation rentals that are family-friendly in Winter Harbor

  • Total vacation rentals

    Explore 70 vacation rentals in Winter Harbor

  • Nightly prices starting at

    Winter Harbor vacation rentals start at ﺩ.ﺇ551 per night before taxes and fees

  • Verified guest reviews

    Over 2,560 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Winter Harbor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Harbor rentals

  • 4.9 Average rating

    Winter Harbor stays are highly rated by guests—averaging 4.9 out of 5!