
Family-friendly holiday 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.

The Cottage
A rustic cottage in the middle of Darthia Farm. The farm sits along the shore of West Bay and a short walking trail brings you from the cottage to the salt water. We grow organic mixed vegetables, herbs and flowers, raise sheep, ducks, chickens, pigs, and work with Haflinger horses. We have a farm store that is open everyday except Tuesdays and Sundays. The property is 15 minutes away from the Schoodic Section of Acadia and is surronded is by countless hiking trails and access to fresh water.

Flower Farm Loft
When you arrive at the Flower Farm Loft you're greeted by our dogs, who will likely jump on you with muddy paws and request fetch and pets. You're immediately surrounded by flowers in our gardens and flower studio. The loft has big east facing windows that look over our farm and surrounding fields. You'll open the curtains in the morning to incredible sunrises over Kilkenny Cove, and end your nights at your private fire pit with immaculate star filled skies that will make it hard to go inside.

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.

Quaint Oceanfront Island Cottage, off Bar Harbor
Feel the stress melt away at Barnacle Hall, a peaceful, romantic getaway w/ stunning water views, just steps to the sea. This snug & welcoming cottage is tucked away in tranquil Burnt Coat Harbor, with its own private rocky beach and a bluff with radiant Maine island sunsets. Truly unwind, stepping into a by-gone era in this quaint cottage, w/ a charming stone fireplace w/ woodstove. Rustic-feeling, with full services. Families welcome! Wifi now available. [NOTE: Not a great option for Acadia]

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.

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.
Popular amenities for Winter Harbor family-friendly rentals
Family-friendly home rentals with a hot tub

Belfast Ocean Breeze

Cute Midcoast Cottage w Hot Tub

Beachfront Guest Cottage - Year-round Hot Tub!

Hot Tub Art Sail Loft. Swans Island

Field of Dreams Tiny Home

10 1BR Acadia Cottage w/AC Open Hearth Inn

Unique, Colorful Off-Grid Cabin

The Seamist Cottage - Converted Historic Barn
Family- and pet-friendly home rentals

Edgewater Cabins

Cozy cottage in Orland Village-Penobscot Bay area

Quiet 2-bedroom house on Acadia's doorstep.

Cozy Cottage on Frenchman Bay

Large adorable 1 bedroom loft with ocean frontage

Hulls Cove Cottage

Hulls Cove Hideaway.

Your Mount Desert Island Base Camp
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.

New Boho Cape with Pool! Fenced yard, pet friendly

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
Quick stats about holiday rentals that are family-friendly in Winter Harbor
Total rentals
70 properties
Nightly prices starting at
£112 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
Destinations to explore
- Montreal Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Portland Holiday rentals
- Salem Holiday rentals
- Newport Holiday rentals
- Island of Montreal Holiday rentals
- Martha's Vineyard Holiday rentals
- Quebec City Area Holiday rentals
- Halifax Holiday rentals
- Bar Harbor Holiday rentals
- Laval Holiday rentals
- Cottage rentals Winter Harbor
- Pet-friendly rentals Winter Harbor
- Rentals with a patio Winter Harbor
- Rentals with outdoor seating Winter Harbor
- Waterfront rentals Winter Harbor
- Rentals with a firepit Winter Harbor
- Rentals with a fireplace Winter Harbor
- House rentals Winter Harbor
- Rentals with a washing machine and dryer Winter Harbor
- Rentals with beach access Winter Harbor
- Family-friendly rentals Hancock County
- Family-friendly rentals Maine
- 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