Family-friendly vacation rentals in Winter Harbor

Find and book unique family-friendly homes on Airbnb

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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Top guest favorite
The kitchen area features a spacious countertop with dark cabinetry and modern appliances. Bright, sloped ceilings are complemented by large windows that provide abundant natural light. A cozy living area is visible, adorned with comfortable seating and decorative elements that reflect the coastal theme.
Apartment in Owls Head
4.95 out of 5 average rating, 113 reviews

Oceanview Escape near Maine Beaches

Located at the end of a private road you will find the area very peaceful with beautiful ocean view sunrises and sunsets and lots of wildlife sightings. This cozy 1000 square foot apartment has been recently renovated for a clean coastal vibe. The house was originally hand built in 2000 by the owner. You will notice the craftsmanship detail, built ins, hand made furniture and unique nautical style throughout the apartment. The kitchen is fully stocked and equipped with stove, full fridge and a new microwave and dishwasher. The living space provides a 50 inch smart TV and queen pull out sofa. Enjoy the vast ocean views from the large living room picture windows. Watch the boats cruising through Penobscot Channel or a local lobsterman hauling their traps. The bedroom offers a queen bed and plenty of closet/storage space. There is a large jacuzzi tub and separate hand tiled shower in the bathroom. Spacious deck off the kitchen/living area provides an outdoor dining area and grill. Enjoy dinner or drinks taking in the salty ocean air and views. At the base of the entry stairs is a separate patio space with propane fire pit shared amongst both living spaces. Located behind the apartment is an adorable playhouse with slide, saucer swings and a rock climbing wall that is shared amongst the neighborhood. Please play at your own risk. WiFi included

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
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
4.95 out of 5 average rating, 241 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 fire pit surrounded by four chairs is positioned by the tranquil waters of Molasses Pond. The scene is framed by a grove of trees, with a dramatic sky stretching overhead, reflecting the calmness of the lake.
Home in Eastbrook
4.99 out of 5 average rating, 152 reviews

The Maine Getaway - Lakefront with Beach

If you are looking for a place to get away and relax, our house on Molasses Pond may be a good fit for you/your family. It is a hidden gem down a dirt road away from hustle and bustle. Peace and quiet is what you’ll find, along with a gorgeous view. It’s a great place for swimming, kayaking, paddle boarding, grilling, fishing, and laying on the hammock. We try to provide you with all the necessities you may need and are happy to answer any questions. We hope you enjoy it as much as we do!

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.

Superhost
A modern treehouse stands elevated on stilts among the trees, featuring a blend of gray siding and white trim. Sturdy wooden stairs lead to a welcoming entrance adorned with flower boxes. Lush greenery surrounds the structure, enhancing the serene forest setting.
Treehouse in Hancock
4.94 out of 5 average rating, 565 reviews

Acadia Treehouse near Bar Harbor - Private Luxury

Escape to a secluded luxury treehouse in the forest of Maine. Unwind in the spa-like full bath with a jacuzzi and sauna. Includes 1 bedroom and loft with 2 queen beds, full kitchen, fireplace, 2 screened porches & outdoor shower. Perfectly located for visiting Acadia National Park, ATV trails and scenic drives. Whether soaking in the jacuzzi, relaxing by the fire, or unwinding on the porch to the sound of rustling leaves, this luxury treehouse is a getaway you’ll never forget

Guest favorite
A cozy waterfront home is set against a backdrop of lush greenery. A spacious deck spans across the front, leading to a circular fire pit area surrounded by Adirondack chairs, inviting relaxation and outdoor gatherings.
Home in Franklin
4.95 out of 5 average rating, 129 reviews

Waterfront near Acadia | Hot Tub| Kayaks| Bay View

Welcome to the 'Maine Squeeze'- where morning coffee tastes better on your private waterfront deck and every sunset over Hog Bay feels like a personal show just for you. Located just 40 minutes from Acadia National Park, this cozy coastal retreat offers the perfect blend of adventure and relaxation. Imagine kayaking right from your backyard, soaking in the hot tub under a canopy of stars, and falling asleep to the gentle sounds of the bay.

Guest favorite
An outdoor deck is featured, showcasing comfortable seating with cushions and decorative pillows. The glamping tent entrance is framed by wooden posts, leading into a well-lit interior with natural decor. Potted yellow flowers add a touch of color against the earthy tones of the surrounding woods.
Tent in Bar Harbor
4.93 out of 5 average rating, 144 reviews

Bear tent, Airbnb fees paid by host.

4 miles from Acadia. Relax, re-charge! Our tents have all the comforts of home. Linens, towels, bath products and kitchen supplies. Just 4 miles from Acadia N.P. This tent has a full bathroom, 2 queen beds, a bunk bed, kitchenette, kitchen table and outside deck. There is a communal fire pit with free wood. We have boardgames and outside games the family can enjoy. Check out the Woods of Eden Glampground in Bar Harbor.

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, 341 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
The shoreline is captured at sunset, with gentle waves lapping against the soft sandy beach. A muted sky filled with clouds reflects the fading light, while a distant silhouette of trees marks the edge of the beach, enhancing the serene coastal scene.
Home in Jonesport
4.99 out of 5 average rating, 100 reviews

Escape to Sandy River Beach

Bella Vista is a cozy, 2 bedroom house with views of Englishman's Bay and Roque Island. The house is set just a few feet away from the soft white sand of Sandy River Beach. You will enjoy magnificent ocean views and comfy accommodations. Stroll the ½ mile sandy beach collecting sea glass and other treasures washed in by the waves. At low tide, hike across the sand bar to explore a nearby island.

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.

Superhost
An open studio space features vaulted ceilings with wooden beams. A spacious bed is positioned next to a bright window, while a striped sofa provides additional seating. A television and lamp are included, alongside a wooden side table, creating a comfortable living area.
Condo in Bar Harbor
4.79 out of 5 average rating, 225 reviews

Sunset Studio the Heart of Bar Harbor (King Bed)

Explore the best of Maine from this 2nd-story studio apartment! Drive just 5 minutes to explore Acadia National Park, or walk 3 minutes to discover a plethora of dining and shopping downtown. Bar Island sandbar sunrises and sunsets are only a 4-minute walk away. Sleeps 4. No animals please, no exceptions, our cleaning lady is allergic.

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.ﺇ1,135ﺩ.ﺇ918ﺩ.ﺇ918
Avg. temp-7°C-6°C-1°C6°C13°C18°C21°C20°C16°C9°C3°C-3°C

Quick stats about vacation rentals that are family-friendly in Winter Harbor

  • Total vacation rentals

    Explore 80 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 2,720 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 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!