
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 80 vacation rentals in Winter Harbor

Nightly prices starting at
Winter Harbor vacation rentals start at G$31,374 GYD per night before taxes and fees

Verified guest reviews
Over 2,710 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 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.

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-Mr Teach the roo may crow (early!) 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, (either indoor or outdoor) and a bucket-style compost toilet is in the apartment. There’s a full bed and a fold out couch.

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.

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.

Artsy Tiny House & Cedar Sauna
Our family is excited to share our tiny house with you! Located on our artist collective farm, this is our favorite place on earth. It’s off grid, cottage core, and has a beautiful & fragrant cedar sauna. We are 27 minutes from Acadia National Park and surrounded by truly gorgeous local beaches. We offer super comfy beds, an outdoor shower, twinkle lights, summer nights filled with fireflies, bright maples in the fall, and cozy winter movie nights in a bed alcove like on a boat.

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.

Schoodic Seaside Duplex
This newly renovated duplex is conveniently located in the heart of Winter Harbor in the quiet neighborhood of Ocean Heights. Guests can look forward to being a short walk away from all of Winter Harbor's own eateries, businesses, and sights to see. This listing is located near Acadia National Park’s Schoodic Point portion of the park. The Acadia National Park section on Mount Desert Island is an approximate 50 minute drive.

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.

Waterfront Sea Cottage w/ Fire Pit, 1 dog, waterto
Waterfall Sea Cottage is a charming 2 bedroom cottage with breathtaking views from every window. Enjoy the warmth of the massive fireplace with gas logs, or relax on the spacious deck overlooking the waterfalls. Use our kayak and 2 stand up paddle boards to put in the water at high tide. Your 1 dog is ok.
Popular amenities for Winter Harbor family-friendly rentals
Family-friendly home rentals with a hot tub

The Acadia Gateway House

Waterfront near Acadia | Hot Tub| Kayaks| Bay View

6 Lovely 1Br Acadia Apartment Open Hearth Inn

Cute Midcoast Cottage w Hot Tub

Modern Cabin in the Pines • Hot Tub + Near Acadia

Field of Dreams Tiny Home

The Seamist Cottage - Converted Historic Barn

Delight<Farmhouse
Family- and pet-friendly home rentals

Bayview Cottage on the Atlantic

Coyote's Den at The Howling Woods

Stonington Harbor Cottage

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

Bayview House 1br 2ba Stunning Harbor Views

Acadia Treehouse near Bar Harbor - Private Luxury

Cabin In The Woods: Little Loon

Driftwood Cottage
Family-friendly home rentals with a pool

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

New Boho Cape with Pool! Fenced yard, pet friendly

Ocean View Lawn Cottage - Newly Renovated 2024

Peaceful 4 Bedroom Maine Retreat with Private Pool

Three Sisters Retreat

Loon Sound Cottage, On the Water

Large MDI house w/pool perfect for groups+families

Indoor Pool*Hot Tub*Sauna*Game Room*Near Acadia
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$52,290 GYD | G$52,290 GYD | G$52,290 GYD | G$47,061 GYD | G$52,290 GYD | G$59,610 GYD | G$70,068 GYD | G$75,297 GYD | G$63,793 GYD | G$64,630 GYD | G$52,290 GYD | G$52,290 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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