Family-friendly vacation 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.

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Guest favorite

Home in Stetson

4.96 out of 5 average rating, 174 reviews

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

Guest favorite

Cabin in Steuben

4.97 out of 5 average rating, 183 reviews

*Stunning Views* Oceanfront Chalet

Oceanfront cabin perched on the edge of Dyer Bay surrounded by large cedar and spruce trees. A perfect retreat nestled in a quiet, private neighborhood off the beaten path. This is where you get away from it all, and enjoy proximity to all the best of Downeast. The view is spectacular, and wildlife abounds. Watch the lobster boats work their traps just in front of the house. Jun 15- Oct 15 Friday-Friday weekly rental. Not appropriate for small children. Sorry, NO PETS , we're allergic :-(

Guest favorite

Home in Hancock

4.99 out of 5 average rating, 142 reviews

Water's Edge-Oceanfront with Stellar View

Water’s Edge offers panoramic coastal water views in a 2-Bedroom+Loft, 1-Bath vacation cottage located feet from the shore. Ideally located between Acadia National Park’s Schoodic Peninsula and Mt Desert Island, your serene cottage has private access to the coast with wonderful views of Frechman Bay and Cadillac Mountain. Explore all the beauty of Acadia National Park, climb local mountains, kayak the Mt Desert Narrows or just watch the tides and mountains from your private deck!

Guest favorite

Cottage in Bar Harbor

4.96 out of 5 average rating, 301 reviews

Ledgewood Grove Cottage in Bar Harbor

Year-round! This tidy cottage comes fully equipped for a pleasant stay in Bar Harbor. The perfect location, tucked off the main road with easy access, puts guests a 10 min. drive from downtown Bar Harbor, and a 6 min. drive from the Acadia National Park entrance and visitor center. This property is located just a few minutes walk from the Free Acadia Shuttle bus route(seasonal). Ledgewood Grove includes a full-size washer/dryer, WIFI, satellite TV, outdoor gas grill, & much more!

Guest favorite

Cottage in Hancock

4.99 out of 5 average rating, 354 reviews

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.

Guest favorite

Rental unit in Bar Harbor

4.99 out of 5 average rating, 162 reviews

Huckleberry Suite - Intown Bar Harbor

This 1 bedroom, second floor apartment, located on a quiet residential cul-de-sac in downtown Bar Harbor, is perfect for a couple or small family. Bar Harbor’s waterfront, our downtown, Bar Island, and the Island Explorer Bus service are only a few blocks away. The Explorer provides free access to parts of Acadia National Park. Huckleberry is available by the week, June - September with a Saturday check in. October - May, our Town requires a 4 night minimum stay.

Guest favorite

Guesthouse in Addison

4.94 out of 5 average rating, 104 reviews

Buddy's Basin

Bright, sunny apartment with a Maine theme. Owners next door will be happy to welcome guests. One bedroom with a single bed and a queen bed. Full bathroom with tub and usual amenities. Open kitchen / living room area with sleep sofa, full size refrigerator and stove, small appliances, dishes, etc. Cable tv and internet included. Lots of parking - bring your atvs, canoes, etc. Weber gas grill on deck for guest use.

Guest favorite

Rental unit in Ellsworth

4.94 out of 5 average rating, 290 reviews

Coastal Studio in Ellsworth

This comfortable, furnished, studio apartment is only 30 minutes to Acadia National Park. Come enjoy a peaceful destination with beautiful, distant views of the mountains. Includes some outdoor living with your own fire pit area, a bundle of wood, and a propane grill. Sleeping arrangements include 2 queen size beds and/or Pack N Play. We are pet friendly, but ask that you notify us if you are bringing your pet.

Guest favorite

Chalet in Gouldsboro

4.93 out of 5 average rating, 286 reviews

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

Guest favorite

Cottage in Mount Desert

4.97 out of 5 average rating, 437 reviews

Cottage by Acadia National Park

Located by the Giant Slide Trail and bordering Acadia National Park the nature enthusiast will enjoy the comfort and central location of this cottage on Mt. Desert Island. Making touring in Acadia easy with trails, sites, and Bar Harbor within easy access. Walk right from the cottage to access the carriage roads and the Giant Slide Trail which leads up Sargeant Mountain.