
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$31,373 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.

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.

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.

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.

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.

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.

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

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.

320 Ft Of Private Beachfront w/ Stargaze Platform!
🌊 Welcome To Compass Point Cottage 🌊 Placed Below A Winding Driveway At The Edge Of Compass Point, Our Beachfront Cottage Rests 20 Feet From The Water's Edge...Surrounded On Two Sides By Over 320 Feet Of Private Shoreline With Views Of Petit Manan Lighthouse In The Distance!
Popular amenities for Winter Harbor family-friendly rentals
Family-friendly home rentals with a hot tub

A waterfront home on the rugged Maine coast.

Field of Dreams Tiny Home

Unique, Whimsical Off-Grid Cabin

Hot Tub Art Sail Loft. Swans Island

Modern Cabin in the Pines • Hot Tub + Near Acadia

Acadia Pines Retreat HotTub-10 Min Downtown Bangor

Acadia Treehouse near Bar Harbor - Private Luxury

Cute Midcoast Cottage w Hot Tub
Family- and pet-friendly home rentals

Long Cove Hideaway

Timberframe Cottage on Organic Farm

New Modern Cabin with RV Pad near Acadia

2026 Summer Waterfront! Hi-Speed Wifi on Flat Bay

Bayview Cottage on the Atlantic

Flanders Bay Cabins (Cabin 9 - 1BR)

Early Riser barn-loft on Organic farm near Acadia

Hulls Cove Cottage
Family-friendly home rentals with a pool

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

Indoor Pool*Hot Tub*Sauna*Game Room*Near Acadia

Bar Harbor, near Acadia with seasonal dock & pool

Camping Cabin

New Boho Cape with Pool! Fenced yard, pet friendly

Camping Cabin at Wild Acadia

Gorgeous house with a view

Acadia get away.! With pool and hot tub
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$52,289 GYD | G$52,289 GYD | G$52,289 GYD | G$52,289 GYD | G$67,557 GYD | G$72,577 GYD | G$70,067 GYD | G$75,296 GYD | G$63,793 GYD | G$64,629 GYD | G$52,289 GYD | G$52,289 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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