
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.

Early Riser barn-loft on Organic farm near Acadia
A unique offering for those who want a true farm experience! A clean, rustic above-barn space. Farm animals live below-Winston the roo may crow (early!) Chadde our pet pig may grunt, chickens will cluck! There is a 2 burner stove, cold water sink seasonally(jugs provided in winter) a dorm fridge, and basic kitchen ware. Tea and coffee provided, veg & eggs for sale The shower is at the main house, and a bucket-style compost toilet is in the apartment. There’s a full bed and a fold out couch.

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

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

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!

Driftwood Cottage
This is the million dollar view on the Schoodic Peninsula. Sit on your private deck and private beach, sipping wine, while gazing across Frenchman Bay as the sun sets over Cadillac Mountain. Watch lobster boats crisscross the bay while eagles soar overhead.
Popular amenities for Winter Harbor family-friendly rentals
Family-friendly home rentals with a hot tub

Belfast Ocean Breeze

Waterfront near Acadia | Hot Tub| Kayaks| Bay View

Cute Midcoast Cottage w Hot Tub

Beachfront Guest Cottage - Year-round Hot Tub!

Birch Hill Cabin w/Hot Tub

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!

Quiet 2-bedroom house on Acadia's doorstep.

Large adorable 1 bedroom loft with ocean frontage

Moose Cabin Getaway Close to Acadia in Maine

Hulls Cove Cottage

Hulls Cove Hideaway.
Family-friendly home rentals with a pool

Lovely 1 bedroom loft above garage, with big yard.

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

Coastal Retreat with Pool and Cheerful Vibes

The Jarvis Homestead | Historic Maine Mansion

Loon Sound Cottage, On the Water

Park Place in the Heart of Bar Harbor

Ocean View Retreat with Pool / Hot Tub

Main Street Suite with Waterfront Resort Access
Quick stats about holiday rentals that are family-friendly in Winter Harbor
Total rentals
70 properties
Nightly prices starting at
$182 SGD before taxes and fees
Total number of reviews
2.1K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi
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- Acadia National Park
- Northeast Harbour Golf Club
- Sandy Point Beach
- Sand Beach
- Kebo Valley Golf Club
- Bear Island Beach
- Lighthouse Beach
- Spragues Beach
- Three Island Beach
- Wadsworth Cove Beach
- Narrow Place Beach
- Driftwood Beach
- Islesboro Town Beach
- North Point Beach
- Hero Beach
- Hunters Beach
- Gilley Beach
- Billys Shore
- Cellardoor Winery
- Penobscot Valley Country Club
- Bar Harbor Cellars
- Pebble Beach
- Bartlett Maine Estate Winery and Distillery
- Catherine Hill Winery