
Family-friendly holiday rentals in Winter Harbor
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Winter Harbor

Total holiday rentals
Explore 90 holiday rentals in Winter Harbor

Nightly prices starting at
Winter Harbor holiday rentals start at $192 SGD per night before taxes and fees

Verified guest reviews
Over 2,810 verified reviews to help you choose

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
80 of Winter Harbor holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Harbor rentals

4.9 Average rating
Winter Harbor stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated family-friendly rentals in Winter Harbor
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Maine Country Home Young
Take it easy at this unique and tranquil getaway. This little country home sits in town in the fishing village of Winter Harbor, Maine. Explore Schoodic Point, a part of Acadia National Park, while hiking, fishing, bicycling, kayaking, and picnicking at Frazer Point.Several area restaurants are within walking distance and serve up Maine traditional fare.Want to enjoy Bar Harbor as well? Take the ferry from the marina and experience sea life such as dolphins, seals, or a bald eagle on your trip.
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Stylish ocean-view home on Acadia's Schoodic Loop
This stylish, former 1940s schoolhouse is one of just a few homes located along Acadia's scenic Schoodic Loop; guests can virtually hike or bike by stepping out the back door. Enjoy our crowd-free corner of Acadia or drive 7 min to the ferry for a charming boat ride to Bar Harbor. Alternatively, head up the coast for more hikes, picturesque fishing villages, quirky shops and quintessential Maine culture. At home, enjoy books, original art, a curated record collection and fresh local lobster.
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Steps from Acadia National Park
This bungalow is located closer to the national park than any other cottage rental on the Schoodic Peninsula. The interior is charming and airy with everything you could possibly need. Walk to the ocean and enjoy coffee along the shore in Acadia National Park. At night, marvel at the stars you feel like you could reach up and touch. Our night skies are among the best in the country. In daylight walk or ride a bicycle around our scenic 6-mile loop road with one stunning view after another.
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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.
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Wonderful Winter Harbor Retreat!
Relax with the whole family at this charming and peaceful home. Located in central Winter Harbor, walking distance to restaurants, shops and beautiful water views. Bike or drive the 6-mile Acadia National Forest Park loop, which is just 3 miles away. The scenic view around the park is spectacular. Great hiking. Short ferry ride to Bar Harbor, running 4-5 times daily from late May to Columbus Day. Free Island Explorer provides shuttle service in the area and all over Bar Harbor.
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2026 Summer Waterfront! Hi-Speed Wifi on Flat Bay
Summer 2026 ~Visit Acadia Park & Bar Harbor by day & stay here at night. Our 1.4 acre shore-front family retreat began an 18 month renovation Fall of 2018 & only opened recently - Dishwasher, new beds, Hi-speed Internet no data limit. We fell in love with this quiet coastal sanctuary, the perfect place to reconnect with nature while staying on grid. ☪ At night you'll experience deafening silence under the natural light of the stars. High-speed Internet keeps you connected.
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Shore Haven - Oceanfront Home in Corea by the Sea
Peak Season (July & August 2027): Weekly rentals only, Sunday arrival/departure. Enjoy this charming cedar-shingled cottage with 1,850 sq. ft. of single-level living. Features include an open-concept kitchen, dining, living, and sunroom area with spectacular ocean views, 3 bedrooms, 2 baths, and a library off the main bedroom with a double bed. Beautifully landscaped grounds slope gently to 240 feet of dramatic oceanfront.
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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
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Meadow Point Cottage
Meadow Point cottage is located on a very quiet five acre property with panoramic views of Frenchman's Bay and Mount Desert Island. It takes about thirty minutes to drive over to MDI and Acadia National Park. The property has a private beach for kayaking and woods with a picnic area and fire pit. It is a wonderful spot for walking and viewing wildlife; ducks, eagles, shore birds, seals and deer.
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Acadia’s Schoodic Oceanfront Cabin
Enjoy your morning coffee or dinner on the oceanside deck while waves splash underfoot. This home is situated at the mouth of prospect harbor. It’s deck overlooks open ocean with deep water frontage. Take the local ferry to MDI to explore Bar harbor’s restaurants and shops, or stay local and enjoy the less traveled side of Acadia National Park, Schoodic Pennisula (5-10 minute drive).
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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
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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.
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Popular amenities for Winter Harbor family-friendly rentals
Family-friendly home rentals with a hot tub

Unique, Whimsical Off-Grid Cabin
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Hot Tub Time Machine
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Acadia Treehouse near Bar Harbor - Private Luxury
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Modern Cabin in the Pines • Hot Tub + Near Acadia
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Cozy 3BR Acadia Hideaway w/ Hot Tub & Fire pit
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Tranquil lakefront retreat for nature lovers
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Peaceful retreat on Newbury Neck
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15 1Br Cottage Heart of Maine Open Hearth Inn
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Family- and pet-friendly home rentals

The Adventure House
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Bayview Cottage on the Atlantic
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Driftwood Cottage
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Little Gem - Ocean Cottage near Schoodic & Acadia
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Plovers Cottage, Waterfront
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Quaint Oceanfront Island Cottage, off Bar Harbor
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Cozy Cottage on Frenchman Bay
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Harborside~Seaglass Beach~Dock~5 min to Acadia
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Family-friendly home rentals with a pool

Cozy, fun, 3 bedroom home with a pool and Hot Tub.
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Seaswept Cottage
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Indoor Pool*Hot Tub*Sauna*Game Room*Near Acadia
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Large MDI house w/pool perfect for groups+families
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The Jarvis Homestead | Historic Maine Mansion
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Deluxe Cabin C at Wild Acadia
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Your country style Cabin_Acadia_Cabin 16
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Gorgeous house with a view
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When is the best time to visit Winter Harbor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $319 SGD | $319 SGD | $319 SGD | $319 SGD | $413 SGD | $443 SGD | $428 SGD | $460 SGD | $390 SGD | $395 SGD | $319 SGD | $319 SGD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 13°C | 18°C | 21°C | 20°C | 16°C | 9°C | 3°C | -3°C |





