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

The rustic cottage features a charming wooden exterior with a sloped roof, surrounded by lush greenery and colorful flowers. Large windows allow natural light to fill the space. The entryway leads to a welcoming atmosphere, complemented by ample outdoor seating nearby.

Cottage in Gouldsboro

4.93 out of 5 average rating, 210 reviews

The Cottage

A rustic cottage in the middle of Darthia Farm. The farm sits along the shore of West Bay and a short walking trail brings you from the cottage to the salt water. We grow organic mixed vegetables, herbs and flowers, raise sheep, ducks, chickens, pigs, and work with Haflinger horses. We have a farm store that is open everyday except Tuesdays and Sundays. The property is 15 minutes away from the Schoodic Section of Acadia and is surronded is by countless hiking trails and access to fresh water.

Top guest favorite

A vibrant flower garden stretches along a pathway, featuring a variety of blooming flowers in shades of pink, purple, and yellow. Above, string lights create a warm glow as the sky transitions to evening hues of pink and purple, enhancing the outdoor ambiance.

Apartment in Hancock

4.98 out of 5 average rating, 285 reviews

Flower Farm Loft

When you arrive at the Flower Farm Loft you're greeted by our dogs, who will likely jump on you with muddy paws and request fetch and pets. You're immediately surrounded by flowers in our gardens and flower studio. The loft has big east facing windows that look over our farm and surrounding fields. You'll open the curtains in the morning to incredible sunrises over Kilkenny Cove, and end your nights at your private fire pit with immaculate star filled skies that will make it hard to go inside.

Guest favorite

A balcony features two black metal stools positioned near the railing, with a stunning view of the sunrise over the water and countryside. The warm hues of the sun reflect off the landscape, enhancing the serene atmosphere.

Vacation home in Addison

4.96 out of 5 average rating, 104 reviews

Bright, Modern Vacation Home w/ Water Views!

Come stay at this serene, cozy, Down East vacation home with expansive water views! Nestled in the Addison hillside where the Pleasant River meets the sea, this completely renovated getaway offers a modern kitchen & bathroom with brand new appliances, open concept living spaces with water views from every room, and a large deck allowing breathtaking panoramic views of the countryside and skyline. One hour to Acadia and close to the Bold Coast, Jasper Beach, & Schoodic Point—you can't lose!

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, 215 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.

Guest favorite

A modern living area is equipped with a comfortable gray sofa and a light wood coffee table. A flat-screen television is mounted on the wall, complementing views of the outdoor landscape through a large window adorned with natural light.

Condo in Bar Harbor

4.95 out of 5 average rating, 156 reviews

Champlain Overlook in the Heart of Bar Harbor

Second level newly rebuilt unit located in downtown Bar Harbor with incredible views from two 6' picture windows of Champlain, Dorr and Cadillac Mountains. The perfect place to call home when exploring Acadia National Park with multiple restaurants within a short walk. Designated off street parking for 2 cars with self check in and 3 mini splits for individual temp controls. It's a 10min walk from stunning sunrises on the Shore Path and 15min walk to sunsets from the Bar Island sandbar.

Top 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

4.89 out of 5 average rating, 110 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

A spacious house is set among trees, featuring a wide front porch and multiple large windows. A gravel path leads to the entrance, bordered by greenery. The roof is covered with dark shingles, complementing the light-colored siding of the home.

Cottage in Hancock

4.99 out of 5 average rating, 382 reviews

Lillebo

Lillebo is set near the end of a dead end road with a five minute walk yielding views over Frenchman's bay with Sorrento in the near view and Winter Harbor and Bar Harbor in the long view. This homey house is set about 200 feet from the road with no neighbors in direct view. There’s a screen porch on one end of the house and a garage on the other. In the garage there is a ping pong table, corn hole, darts and bikes. There are three adult bikes, one youth bike and one kids bike.

Top guest favorite

The stand-alone cottage is surrounded by lush greenery and trees displaying autumn colors. A small picnic table is seen on the neatly manicured lawn, while a pathway of stone pavers leads to the entrance. The exterior is painted in a calming shade of blue.

Cottage in Mount Desert

4.99 out of 5 average rating, 167 reviews

Cozy Seal Harbor Cottage

We request anyone who stays on our property be fully vaccinated. Thank you for helping to keep our community healthy! This stand along cottage is on the same property as owner's home and includes 1 parking space. 2 bedrooms with full bath, laundry, and a fully stocked kitchen. House abuts Acadia National Park; Seal Harbor Beach and carriage roads are easy walking or biking distance! Only 12 minutes to Bar Harbor and 5 to Northeast Harbor.

Top guest favorite

A view from above captures the cottage set amidst a grassy area, surrounded by trees. In the background, the ocean extends towards the horizon, with hints of shoreline visible. The structure is positioned to showcase its proximity to nature.

Cottage in Lamoine

4.97 out of 5 average rating, 115 reviews

Meadow Point Cottage

Meadow Point cottage is located on a very quiet five acre property with panoramic views of Frenchman's Bay and Mount Desert Island. It takes about thirty minutes to drive over to MDI and Acadia National Park. The property has a private beach for kayaking and woods with a picnic area and fire pit. It is a wonderful spot for walking and viewing wildlife; ducks, eagles, shore birds, seals and deer.

Guest favorite

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

4.87 out of 5 average rating, 130 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

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

4.96 out of 5 average rating, 114 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.

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, 168 reviews

The Adventure House

Our house was named “The Adventure House” by a family of houseguests with 3 fun and lively children. They told us that their time in Maine was filled with fun adventures so the kids started calling the house “The Adventure House” during their stay. We thought that was fitting as we are so close to Acadia National Park and many other pathways to adventures!