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

A charming cottage is framed by tall trees, featuring a steeply pitched roof and an inviting porch. Vibrant flowers adorn the entrance, complementing the rustic wooden facade. The setting offers a serene atmosphere, surrounded by the natural beauty of the forest.

Cabin in Hancock

4.95 out of 5 average rating, 146 reviews

Blackberry Cottage at Crabtree Neck Cottages

PETS MUST BE DISCUSSED. We accept crate trained pets for an extra service fee that we charge after you make your reservation. INFANTS must be mentioned when you request to book and they must be listed as a guest or child. We charge for all people, inlcuding infants. This is a summer cottage that we also rent in the spring and fall when weather permits. It is heated with wood and you will need to use the wood stove. We supply all the firewood you need for fires inside the house. Rental agreement

Guest favorite

A clear night sky filled with stars is viewed above a stylish home surrounded by trees. The house is softly illuminated, highlighting its architecture against the dark backdrop of the forest, creating a serene nighttime atmosphere.

Home in Bar Harbor

4.97 out of 5 average rating, 156 reviews

Family/Friends Getaway Hidden on Mt Desert Island

Escape to our enchanting woodland retreat on MDI, surrounded by Acadia National Park. Secluded at the end of a dirt road, our home borders the 2000-acre Kitteridge Brook forest. Discover tranquility with 3 miles of private trails right outside your door. Ideal for exploring Acadia's magic, our 3-bedroom home features an open concept kitchen, living, and dining area, along with a spacious deck. Perfect for large families or two small families, experience the ultimate oasis in the heart of nature.

Guest favorite

A log cabin is situated on a grassy expanse beside the water, surrounded by trees displaying vibrant autumn foliage. A private dock extends into the lake, providing access for boating activities, while the spacious lawn offers plenty of room for outdoor enjoyment.

Home in Stetson

4.95 out of 5 average rating, 190 reviews

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

Guest favorite

The exterior of a blue house is shown, featuring white trim and a welcoming front door. Lush greenery and vibrant hydrangea flowers frame the entrance, creating a charming appearance. A few windows allow natural light to enter, and the house is complemented by a well-maintained lawn.

Home in Rockland

4.98 out of 5 average rating, 109 reviews

Charming, Family-Friendly Historical In Town Home

STR24-11 Sadler House is an in-town historic home located just blocks from Main Street. We have made it truly convenient for families, with flexible sleeping arrangements in three cozy upstairs bedrooms, two full baths, a fully equipped kitchen, large dining table, living room, and sun room. Walk to shops, restaurants, museums and the harbor in minutes. Our house is the perfect home base for exploring all that the beautiful midcoast has to offer. Ask us about free delivery from Ruckus Donuts!

Top guest favorite

The front exterior of the cottage features a welcoming entrance with a path of bricks leading to wooden double doors. Lush greenery surrounds the property, and flowerpots add a touch of color to the landscape. Tall trees create a natural border, enhancing the secluded feel.

Home in Bar Harbor

4.96 out of 5 average rating, 107 reviews

Skipping Stone on Frenchman's Bay Weekly Rental

Our beachfront home is good for families and pets, with open plan, private bedrooms and an enclosed deck. The beach is perfect for cookouts, walking and exploring. We are nestled down a long gravel drive with quiet neighbors. The main floor bedroom (queen bed) accesses a screened sitting area. The downstairs bedroom (walkout basement) has twin beds and futon chair (single). We are 5 miles from the village, 2.5 miles from Acadia Visitor Center, and .5 miles from an Explorer stop.

Superhost

A panoramic view of the harbor is seen at dawn, showcasing a tranquil sea reflecting the soft colors of the sunrise. Boats are anchored and gently bobbing on the water, framed by silhouettes of trees and distant land. The sky transitions from deep blue to warm oranges and yellows.

Apartment in Southwest Harbor

4.91 out of 5 average rating, 149 reviews

On the water. Walk to Southwest Harbor

If you want to be near the action of an active and interesting harbor, this is the place for you. You will have a front row seat to spectacular morning sunrises over the harbor, the comings and goings of the fishermen and the many boats docked at the marina and anchored in the harbor. This spacious four bedroom two and a half bath home is located at the Great Harbor Marina just half a mile from downtown Southwest Harbor. Walk to restaurants, art galleries, specialty shops and more.

Top guest favorite

A cozy loft area features a slanted ceiling with soft lighting. A TV is positioned on a dark media console beside a basket of toys. A bookshelf holds an array of colorful children's books, and a cushioned chair invites relaxation.

Bungalow in Bar Harbor

4.98 out of 5 average rating, 120 reviews

Hadley Point Hideaway, Quiet & Peaceful

This high-end 2 bedroom bungalow, with loft, is a guest favorite. Airbnb marketed this cottage as one of their most "wish listed" listings in Fall 2024. Hadley Point Hideaway is adjacent to the owners residence and is designed for privacy. This bungalow is nestled in the woods on a desirable road for walking, running & biking. Hadley Point Beach is walking distance from the house. This house is 10 minutes from Bar Harbor and 5 minutes to the Acadia National Park entrance.

Guest favorite

The Victorian-style building features a distinct gabled roof and a covered deck that extends from the second floor. Lush greenery and flowering plants surround the entrance, while decorative trim adds charm to the pale exterior. A quiet street and off-street parking are visible in the foreground.

Apartment in Bar Harbor

4.89 out of 5 average rating, 322 reviews

The Old Charm of Cozy Victorian(downtown)

Victorian style apt (on 2nd floor) with a lot of charms and a deck. Right in downtown, walkable to everywhere, 5 min to island explorer/bus stop, Village green, library, museum, historical churches, kids playground, many restaurants and more. You’ll love it because of the quiet you rarely find in the busy town and the convenience of the location, which allows you to easily catch a free shuttle bus to anywhere in the park without the hassle of driving and parking.

Guest favorite

A cozy living area features a black wood stove providing warmth. A wooden table is set with two glasses and a bottle, inviting relaxation. Windows offer views of the water, while comfortable seating is arranged nearby, enhancing the inviting space.

Guest suite in Penobscot

4.88 out of 5 average rating, 109 reviews

Waterfront Getaway on the coast of Maine.

Cozy waterfront, two bedroom apartment with separate entrance and private deck overlooking the beautiful Maine coast. Walk the shore path through a field, filled with wildflowers, to a private cove on the Bagaduce River. The light filled apartment is located above the garage of a restored antique farmhouse and has beautiful water views from the living room and private deck. The perfect spot for a relaxing vacation on the coast of Maine.

Guest favorite

A spacious deck is shown with views of the surrounding trees and water. A single chair is positioned on the grey wooden surface, inviting moments of relaxation among the natural setting. The edges of the structure frame the scene, blending indoor and outdoor environments.

Home in Mount Desert

4.88 out of 5 average rating, 101 reviews

Pretty Marsh Cottage

This beautiful, light-filled cottage on waterfront property on the western side of Mount Desert Island has picturesque views of the Mount Desert Narrows and access to a private pebble beach. The house is on very secluded wooded property for a nice private getaway. All you will hear are the sounds of birds and waves lapping up on the beach. Just a short drive to all that Acadia National Park has to offer!

Superhost

The cabin features a dark exterior surrounded by tall trees, with a wooden deck extending along the front. A clear pathway leads to the entrance, providing access to the main entrance and steps. Several windows allow natural light into the living space.

Cabin in Southwest Harbor

4.95 out of 5 average rating, 103 reviews

Bluehouse Cottage in Acadia, 5 min walk into town

Charming 4 bedroom, 2 bath traditional wooden cabin situated on 8 acres in Southwest Harbor. Walk into town easily for restaurants, galleries and boutiques. Or walk to the town dock for an adventure to another island. Ferries leave daily to explore outer areas. Acadia easily explored from here, with parts of Southwest Harbor National park land. Ask Marc for a hiking map to explore Acadia.

Top guest favorite

Home in Belfast

4.94 out of 5 average rating, 170 reviews

Charming Belfast home. Walk downtown/water

Enjoy this charming, well-maintained neighborhood, positioned right between downtown and the town park. This house also sits just a block up from quiet public access to the beach. Walk to everything! Exquisitely landscaped backyard. Lovely historic 1920 roots, with fresh, clean, modern updates. Glimpse water through trees.