Family-friendly holiday 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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Top guest favourite
A serene landscape captures the transition of day to night, with the sky filled with shades of purple and pink. Smooth rocks line the water's edge, reflecting the calming colors onto the still surface of the bay. Lush greenery accents the foreground.
Cottage in Milbridge
4.97 out of 5 average rating, 117 reviews

Bayview Cottage on the Atlantic

Nestled at the head of Pigeon Hill Bay, our cottage is surrounded by 20 acres of fields, marshland, private walking paths, and a private pebble beach on the ocean with views of the Atlantic. Acadia National Park is nearby (1 hour plus) or take the ferry (20 minutes away) to BarHarbor. Acadia Park Schoodic Point is a must see (20 minutes). Enjoy our kayaks, our recommended day trips, blueberry picking, visiting white-tailed deer. For a full week stay we serve a lobster shore dinner for two.

Top guest favourite
A rustic fire pit area features four blue Adirondack chairs arranged around a stone circle, set within a grassy space. A small table sits nearby, and a serene tidal cove is visible through the trees in the background.
Campervan/Motorhome in Sorrento
4.91 out of 5 average rating, 133 reviews

Long Cove Hideaway

Newly upgraded to 2018 RV! Escape the tourist madness of Bar Harbor at your own private tidal cove. Camp with the comforts of home, water, power and Wifi. Outdoor grill, awning and lobster cooker for the complete Maine experience. After a hard day of hiking relax by fire pit. The Schoodic National Scenic Byway is on the far side of Long Cove, and you can hear some traffic noise from outside the RV, but for complete silence check out my other two places by looking at "about me" on my profile.

Guest favourite
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, 213 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.

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, 176 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.

Guest favourite
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, 225 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 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
4.89 out of 5 average rating, 122 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 favourite
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, 290 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 favourite
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, 176 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 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
4.93 out of 5 average rating, 328 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 favourite
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
4.94 out of 5 average rating, 834 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

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, 120 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
The cottage is situated along a rocky shoreline, surrounded by vibrant autumn foliage. The water reflects sunlight, enhancing the serene environment. The landscape features a blend of greenery and colorful leaves, framing the inviting coastal setting.
Cottage in Gouldsboro
5 out of 5 average rating, 120 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 family-friendly rentals

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

  • Total rentals

    70 properties

  • Nightly prices starting at

    € 129 before taxes and fees

  • Total number of reviews

    2.6K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    70 properties include access to wifi