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

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, 557 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)

Guest favorite

A serene view of Young's Bay is captured, featuring calm waters reflecting greenery and rocky shores. Lush trees line the edges, creating a natural backdrop, while granite ledges are visible along the water's edge. The tranquil environment suggests a peaceful retreat by the ocean.

Home in Hancock

4.98 out of 5 average rating, 185 reviews

Acadia's Oceanfront CAMP - near Bar Harbor

Oceanfront cottage. 30 minute drive to Bar Harbor! 2 acres, Stunning waterfront and sunset views. Westerly views across Young's Bay. 15 minutes from Schootic Point. What makes this place unique is the privacy you experience as forest meets ocean. Excellent condition, wide pine floors, granite counter tops, quality appliances. The woods have been carefully groomed to open views of the cove framed with beautiful granite ledges. A short distance to Hancock Point and the amenities it has to offer.

Guest favorite

An aerial view captures a contemporary house nestled amidst vibrant autumn foliage alongside a calm bay. The lush green lawn leads to a shoreline with smooth water, while walking pathways and a stone patio can be seen in the garden, integrating seamlessly into the natural landscape.

Home in Trenton

4.93 out of 5 average rating, 291 reviews

Acadia National Park ocean front & garden cottages

Both our houses are designed in the contemporary style. We used custom made decor and cherry tree furniture. A lot of windows, glass doors, bright and open space are inside the house. It is very quiet outside. You most likely will be alone at the beach. We share the whole sea cove with only one neighboring house. It is a pure paradise if you want to live on the beach on your own and within minutes of driving to the main local attractions. You'll be amazed of our botanical garden and landscape.

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, 109 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.

Top guest favorite

Large windows frame expansive views of the serene coastal landscape, allowing natural light to fill the space. A low coffee table is positioned in front of the windows, complementing the neutral tones of the carpet and walls.

Home in Hancock

4.97 out of 5 average rating, 153 reviews

Water's Edge-Oceanfront with Stellar View

Water’s Edge offers panoramic coastal water views in a 2-Bedroom+Loft, 1-Bath vacation cottage located feet from the shore. Ideally located between Acadia National Park’s Schoodic Peninsula and Mt Desert Island, your serene cottage has private access to the coast with wonderful views of Frechman Bay and Cadillac Mountain. Explore all the beauty of Acadia National Park, climb local mountains, kayak the Mt Desert Narrows or just watch the tides and mountains from your private deck!

Guest favorite

A charming wooden cottage stands elevated on a sturdy foundation, framed by lush greenery. The spacious deck features hanging flower baskets that add vibrant color, while a bicycle rests beside the gravel path leading to the garage underneath.

Tiny home in Hancock

4.97 out of 5 average rating, 152 reviews

Treetop Loft at Crabtree Neck Cottages

Pets negotiable. MUST DISCUSS BEFORE YOU REQUEST. Crate trained pets allowed for a fee. DISCOUNT for over 3 nights or dogs under 12 lbs. Ask! Pets come by prior arrangement only. Treetop sleeps 2, or 3 in a pinch. Must discuss well behaved children 6 or older as the deck is high. Owners/guests use garage/laundry below the studio. Kitchenette includes two burner hot plate and large dorm fridge, coffee maker, microwave, and toaster oven. Rental Agreement, PET POLICY, see notes.

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, 371 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

A charming cabin features large windows that allow ample natural light and provide views of the surrounding cedar and spruce trees. The spacious deck showcases colorful buoy decorations, enhancing the outdoor space. The structure is set in a serene, wooded area, promoting a peaceful retreat.

Cabin in Steuben

4.97 out of 5 average rating, 197 reviews

*Stunning Views* Oceanfront Chalet

Oceanfront cabin perched on the edge of Dyer Bay surrounded by large cedar and spruce trees. A perfect retreat nestled in a quiet, private neighborhood off the beaten path. This is where you get away from it all, and enjoy proximity to all the best of Downeast. The view is spectacular, and wildlife abounds. Watch the lobster boats work their traps just in front of the house. Not appropriate for small children. Sorry, NO PETS , we're allergic :-(

Guest favorite

The exterior of the Craney House is shown, featuring a light grey shingle facade and a welcoming porch. A vibrant tree stands nearby, surrounded by a grassy lawn and flower beds. The pathway leads from the house to the street, indicating a peaceful residential setting.

Cottage in Mount Desert

4.98 out of 5 average rating, 204 reviews

Craney "Tree" House near Acadia

Craney House is a comfortable place with character—good for couples, solo adventurers, business travelers, and families (with kids). We affectionately call it our "tree house" because of the jungle that used to obscure the house. We love Otter Creek for its quieter access to what Acadia has to offer—close to the Park Loop Rd, carriage and hiking trails, but it's also only about 5 miles away from Bar Harbor and 10 miles to Seal Harbor.

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, 312 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 solarium features large windows adorned with sheer curtains, allowing natural light to fill the space. A blooming bush with purple flowers and greenery surrounds the exterior, while potted plants contribute to the serene ambiance of the outdoor area.

Apartment in Bar Harbor

4.98 out of 5 average rating, 193 reviews

Lighthouse Retreat, 200 ft from Acadia Nat'l Park!

The Lighthouse Retreat is a studio apartment with a solarium entryway, totally private. Owners quiet and upstairs. We're 200 feet from Acadia National Park. You can be off-road hiking or biking in minutes! Downtown Bar Harbor, boat tours, restaurants, shopping, a mile away. Perfect for couples, friends or anyone wanting to explore unique coast of Maine!

Top guest favorite

A screened-in porch features a wooden table surrounded by four white chairs, with a view of Graham Lake visible through large screens. Soft lighting is provided by hanging bulbs above. Lush greenery surrounds the cabin, creating a serene outdoor atmosphere.

Cottage in Mariaville

4.97 out of 5 average rating, 112 reviews

Restored camp nestled in the Maine woods

Our little camp is ready for your rest and relaxation on Graham Lake, Maine. Quiet setting, 15 miles from Ellsworth and 24 miles from Mount Desert Island. Great for adventuring to Blue Hill and Schoodic Peninsulas. Escape the island crowds and experience Maine how locals do...upta camp! Lovingly restored and available for limited weeks. Now available for winter bookings!