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.

%{current} / %{total}1 / 1
Top guest favorite
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.

Guest favorite
A charming bungalow sits nestled among trees, featuring a light wood exterior with a bright blue door. Snow covers the ground, and a pathway leads to the entrance. Two windows on either side of the door provide natural light, enhancing the cabin's inviting presence.
Farm stay in Franklin
4.91 out of 5 average rating, 572 reviews

Boreal Blueberry Bungalow - Organic Farm Getaway

This sweet bungalow is located on a tucked-away organic farm, 45 minutes from Bar Harbor and Acadia National Park, and directly abutting the Downeast Sunrise Trail and thousands of acres of conservation land. Newly crafted space with pine interior and cork flooring. For folks who appreciate simple living but want a cozy bed! Cot available for third person. Full size mattress, all bedding, stove with oven, pots, pans and dishes, small fridge and sawdust based composting toilet (on back porch)

Top guest favorite
Tiny home in Surry
4.96 out of 5 average rating, 152 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, 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 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, 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 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, 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 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, 288 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 rustic cabin exterior is presented, featuring a wooden porch with two blue Adirondack chairs. A small table with a lantern stands beside the entrance. Surrounding trees provide a natural backdrop, and a flower pot adds a touch of color near the door.
Tiny home in Eastbrook
4.92 out of 5 average rating, 106 reviews

Camp Ottah' Knot Rustic Camping Cabin 2

10 X 12 Rustic Cabins. Two twin beds in each cabin. Each cabin includes two Adirondack Chairs, Firepit, small table, and two chairs indoors, 2 LED powered lanterns and 1 fan, 5 gallons of potable water, simple outdoor kitchen table, a picnic table, propane on demand shower house, The bathroom facility is port-o-Potty shared with the other cabin or a compostable toilet. Both options are available. These are OFF the grid. No power or water in the two cabins.

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, 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 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, 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

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, 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 favorite
A modern log cabin is set amidst a clearing, surrounded by tall trees. A stone patio with seating is visible, complemented by natural rocky formations and open grassy areas. The cabin's exterior features a dark wood finish, with a welcoming porch extending from the front.
Cabin in Gouldsboro
4.99 out of 5 average rating, 188 reviews

40 Acre Wooded Paradise w/ Firepit Near Acadia

🌲 Welcome To Rocky Roods Cabin 🌲 Nestled In A Clearing and Surrounded By Woods, You'll Find Our Serene & Modern Log Cabin Awaiting Your Adventurous Spirit. Experience 40 Acres Of Privacy w/ On-Site Hiking Trails , Deeded Beach Access and Land Untouched By Light Pollution Where The Night Sky Shines Bright Around Your Own Wood-Burning Outdoor Firepit!

Popular amenities for Winter Harbor family-friendly rentals

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

  • Total rentals

    70 properties

  • Nightly prices starting at

    G$31,369 GYD 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