
Family-friendly holiday rentals in Winter Harbor
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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.

Tiny House at Wooded Bliss Homestead
On the edge of our family homestead overlooking meadow & forest, this tiny house offers a quiet, cozy refuge only 40 minutes from Acadia National Park. There's a twin daybed on the ground floor & a double futon in the loft. Full kitchen & tiny bathroom with shower too. A heat pump keeps the place toasty warm or nice and cool. The tiny house and meadow are very private on the edge of the property, and just for you. Our family's gazebo, fire pit, hammock, trail & garden are shared with guests.

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.

Hemlock Cabin.
Nestled in beautiful Hemlock grove is this cozy cabin. Its equiped with all the necessities of home to make your stay comfortable. Guests will have private access to Scammons Pond, also known as, R. Lyle Frost Managment Area. Its a fun place to kayak and fish. From the cabin its about a 45 minute drive to Acadia National Park or Schoodic Point. Besides Acadia, there is local hiking, nearby shopping, local restaurants, the Sunrise Trail, and other Maine adventure just waiting to be explored.

Whitetail by the River, Acadia National Park 10m
Whitetail Cottage - 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Tiny home with WIFI is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature. Enjoy a stroll to the water, privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 & cozy for 4. Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

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.

Precipice Studio w/Loft in the Heart of Bar Harbor
Located just a 5-minute drive from Acadia National Park. This studio apartment w/loft is ideal for exploring the best outdoor recreation in Maine! Walk just 3 minutes to sample a plethora of dining and shopping options in downtown Bar Harbor. It is nicely tucked away in a quiet neighborhood of historic Victorian homes just blocks away from stunning sunrises on the Shore Path and sunsets on the sand bar. Sleeps 4. No animals please, no exceptions, our cleaning lady is allergic.

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.

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.

The Tiny House with the Enormous View of Acadia
The Tiny House on Goose Cove is the perfect place from which to enjoy your visit to Acadia National Park. Set on three acres of shore front property, the house features spectacular views of Mount Desert Island. The entrance to the Park, and the shops and restaurants of Bar Harbor, are just 20-25 minutes away by car. And when you've had enough of the bustle and crowds, you can retreat to the peace and serenity of this beautiful property.

Forested Cabin Decorated For The Holidays!
Wanderers | Travelers | Explorers Stained In Raven Black and Cloaked From Peering Eyes, Stonebrook Cabin Sits Proudly Concealed Behind Maine's Mighty Pines. Eclectic, Romantic and Streamside, Stonebrook Cabin Features An Expansive Sundeck Overlooking 5 Acres Of Forested Privacy and Beach Access 5 Minutes Away! 🎅 Ho, Ho Ho...Tis The Season 🎅 Stonebrook Cabin Will Be Decorated For The Holidays Through December!

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
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

Field of Dreams Tiny Home

Modern Cabin in the Pines • Hot Tub + Near Acadia

Waterfront with Hot Tub

Boathouse Cabin on the Ocean
Family- and pet-friendly home rentals

Bayview Cottage on the Atlantic

Up Back Cottage

Plovers Cottage, Waterfront

Long Cove Hideaway

Cozy Cottage on Frenchman Bay

Camp Ottah' Knot Rustic Camping Cabin 2

Apt A, 30min drive 2 Acadia National Park

Hulls Cove Cottage
Family-friendly home rentals with a pool

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

Coastal Retreat with Pool and Cheerful Vibes

New Boho Cape with Pool! Fenced yard, pet friendly

The Jarvis Homestead | Historic Maine Mansion

Loon Sound Cottage, On the Water

Ocean View Retreat with Heated Pool / Hot Tub

Acadia get away.! With pool and hot tub

Main Street Suite with Waterfront Resort Access
When is the best time to visit Winter Harbor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $341 NZD | $428 NZD | $428 NZD | $386 NZD | $428 NZD | $488 NZD | $574 NZD | $617 NZD | $523 NZD | $499 NZD | $406 NZD | $422 NZD |
| 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 |
Quick stats about holiday rentals that are family-friendly in Winter Harbor

Total holiday rentals
Explore 70 holiday rentals in Winter Harbor

Nightly prices starting at
Winter Harbor holiday rentals start at $257 NZD per night before taxes and fees

Verified guest reviews
Over 2,560 verified reviews to help you choose

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
70 of Winter Harbor holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Winter Harbor rentals

4.9 Average rating
Winter Harbor stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Rentals with outdoor seating Winter Harbor
- Rentals with a washing machine and dryer Winter Harbor
- Waterfront rentals Winter Harbor
- Rentals with a patio Winter Harbor
- Rentals with a fire pit Winter Harbor
- Rentals with a fireplace Winter Harbor
- Pet-friendly rentals Winter Harbor
- House rentals Winter Harbor
- Cottage rentals 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
- Acadia National Park Pond
- Sandy Point Beach
- Lighthouse Beach
- Sand Beach
- Bear Island Beach
- Kebo Valley Golf Club
- Spragues Beach
- Wadsworth Cove Beach
- Islesboro Town Beach
- Narrow Place Beach
- North Point Beach
- Three Island Beach
- Driftwood Beach
- Hero Beach
- Billys Shore
- Gilley Beach
- Hunters Beach
- Asper Beach
- Cellardoor Winery
- Bar Harbor Cellars
- Penobscot Valley Country Club
- Echo Lake Beach




