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

Total vacation rentals
Explore 90 vacation rentals in Winter Harbor

Nightly prices starting at
Winter Harbor vacation rentals start at G$31,376 GYD per night before taxes and fees

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
80 of Winter Harbor vacation rentals include wi-fi 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.

The Cabins at Currier Landing Cabin 3: Pine
Relax in this stylish, cozy & bright queen bed studio cabin. The Cabins at Currier Landing - featured in Dwell as “Three Magical Tiny Cabins Take Root in a Maine Forest” - are located on the Thos. Currier Saltwater Farm. Glimpses of water & access to 300’ of our shore on the Benjamin River Harbor. 2 seasonal cabins. 1 year round studio cabin. Centrally located on the Blue Hill Peninsula, near Deer Isle, the cabins afford access to outdoor activities, cultural events, restaurants & shops.

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.

*New* Wharf house w/Hot Tub, Sauna, Harbor Views
*New* to the market! Be among the first to enjoy this completely renovated waterfront retreat overlooking Prospect Harbor, Maine. Featuring 2 luxurious master suites, a hot tub, and a sauna perched above the harbor, you’ll wake to breathtaking views of the lighthouse and working lobster boats. Watch fishermen bring in the day’s catch—or buy fresh lobster right from the dock. Experience the authentic charm of coastal Maine in an unforgettable setting. 5 mins to Acadia National Park Schoodic.

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.

Schoodic apartment
Tastefully decorated and well maintained older apartment that is located a little over a mile from the Schoodic section of Acadia National Park where you can bike or hike the trails. What you see in the pictures is what you get. We have been renting to tourists for well over twenty years now. It's not quite all-inclusive but stocked with everything we can think of that you may forgotten or need to get your vacation started. It is perfect for thrifty travelers like ourselves.

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.

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.

The Peaceful Puffin: Walk to Shops, Dining & Ferry
The "Peaceful Puffin Cottage" is a cozy 1BR, 1BA retreat in the heart of Winter Harbor. Enjoy quiet mornings, then walk or bike to local cafés, a brewery, or explore the Schoodic Peninsula—the peaceful, lesser-known part of Acadia National Park. This is the perfect location for those seeking an authentic Down East Maine Coast experience, this charming seaside escape offers comfort and coastal charm for a relaxing getaway.

Home away from Home
Nestled in a quiet location! Screened in balcony to enjoy the view! Cleared path to the oceanfront to enjoy sun bathing or sea glass hunting Not far from Schoodic Acadis National Park which offers some serene hiking and biking paths Two ferries located in Winter Harbor to go exploring in Bar Harbor There are several fantastic Restaurants I have left plenty of local information at the property

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).

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

Waterfront near Acadia | Hot Tub| Kayaks| Bay View

Beachfront Guest Cottage - Year-round Hot Tub!

Hot Tub Art Sail Loft. Swans Island

Modern Cabin in the Pines • Hot Tub + Near Acadia

Field of Dreams Tiny Home

Acadia Treehouse near Bar Harbor - Private Luxury

Unique, Whimsical Off-Grid Cabin

A waterfront home on the rugged Maine coast.
Family- and pet-friendly home rentals

Coyote's Den at The Howling Woods

Rustic Manset Tiny House

Long Cove Hideaway

Cozy Cottage on Frenchman Bay

Boreal Blueberry Bungalow - Organic Farm Getaway

Cabin In The Woods: Sleepy Deer

Driftwood Cottage

Hulls Cove Cottage
Family-friendly home rentals with a pool

Camping Cabin at Wild Acadia

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

The Jarvis Homestead | Historic Maine Mansion

New Boho Cape with Pool! Fenced yard, pet friendly

SugarMaple: New 2-Bedroom Apartment, Screen Porch.

Ocean View Lawn Cottage - Newly Renovated 2024

Peaceful 4 Bedroom Maine Retreat with Private Pool

Bar Harbor, near Acadia with seasonal dock & pool
When is the best time to visit Winter Harbor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$52,294 GYD | G$52,294 GYD | G$52,294 GYD | G$47,065 GYD | G$52,294 GYD | G$59,615 GYD | G$70,074 GYD | G$75,303 GYD | G$63,799 GYD | G$64,635 GYD | G$52,294 GYD | G$52,294 GYD |
| 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 |
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