
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.

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.

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)

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.

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.

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.

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.

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.

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.

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.

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

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.

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
Family-friendly home rentals with a hot tub

Belfast Ocean Breeze

Beachfront Guest Cottage - Year-round Hot Tub!

Hot Tub Art Sail Loft. Swans Island

11 Cute 1Br Acadia Cottage Open Hearth Inn

Secluded Retreat w/ Luxe Hot Tub & Forest Views

A comforting sweet off grid cabin near the beach!

The Seamist Cottage - Converted Historic Barn

A-Frame, Hot Tub, Firepit, Oceanfront, Pets
Family- and pet-friendly home rentals

Plovers Cottage, Waterfront

Cozy cottage in Orland Village-Penobscot Bay area

Modern Condo #3!

Rustic Manset Tiny House

Quiet 2-bedroom house on Acadia's doorstep.

Large adorable 1 bedroom loft with ocean frontage

Hulls Cove Hideaway.

Coastal Studio in Ellsworth
Family-friendly home rentals with a pool

Lovely 1 bedroom loft above garage, with big yard.

Deluxe Cabin A at Wild Acadia

Cozy, fun, 3 bedroom home with a pool and Hot Tub.

Coastal Retreat with Pool and Cheerful Vibes

The Jarvis Homestead | Historic Maine Mansion

Lawn Cottage - Newly Renovated 2024

Loon Sound Cottage, On the Water

Park Place in the Heart of Bar Harbor
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
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- Family-friendly rentals Hancock County
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- Family-friendly rentals United States
- Acadia National Park
- Northeast Harbour Golf Club
- Sandy Point Beach
- Sand Beach
- Bear Island Beach
- Kebo Valley Golf Club
- Lighthouse Beach
- Spragues Beach
- Driftwood Beach
- Three Island Beach
- Wadsworth Cove Beach
- Narrow Place Beach
- Islesboro Town Beach
- Hero Beach
- North Point Beach
- Hunters Beach
- Billys Shore
- Gilley Beach
- Cellardoor Winery
- Penobscot Valley Country Club
- Bar Harbor Cellars
- Bartlett Maine Estate Winery and Distillery
- Pebble Beach
- Catherine Hill Winery