Family-friendly vacation rentals in Winter Harbor
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winter Harbor
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Harbor family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Searsport
4.82 out of 5 average rating, 293 reviewsLakefront Vacation Apartment in Searsport ME
Oct 24 – 31
Home in Surry
4.89 out of 5 average rating, 168 reviewsPeaceful retreat on Newbury Neck
Dec 24 – 31
Cabin in Appleton
4.88 out of 5 average rating, 276 reviewsRaven's Crossing - Kate's Cottage
Oct 6 – 13
Home in Holden
4.96 out of 5 average rating, 208 reviewsChalet Central
Jan 15 – 22
Cottage in Verona Island
4.88 out of 5 average rating, 154 reviewsNashport on the Penobscot
Mar 5 – 12
Guest suite in Lincolnville
4.95 out of 5 average rating, 44 reviewsWaterfront Loft w/ Bold Ocean Views
Nov 9 – 16
Farm stay in Searsport
4.92 out of 5 average rating, 105 reviewsLatham Blueberry Farm for up to 6 guests.
Dec 20 – 27
Cottage in Penobscot
4.88 out of 5 average rating, 41 reviewsBeach cottage on Penobscot Bay
Apr 6 – 13
Family- and pet-friendly home rentals
Dome in Tremont
4.82 out of 5 average rating, 197 reviewsLittle Frog at The Howling Woods
Dec 9 – 16
Cabin in Deer Isle
4.89 out of 5 average rating, 129 reviewsLong Cove Artist Cottage
May 12 – 19
Cabin in Bar Harbor
4.89 out of 5 average rating, 286 reviewsEden on Norway
Jul 26 – Aug 2
Guesthouse in Tremont
4.92 out of 5 average rating, 147 reviewsFairview Cottage
May 8 – 15
Cottage in Bar Harbor
4.98 out of 5 average rating, 118 reviewsAcadia Access Cottage-Bar Harbor Tesla charger.
Mar 19 – 26
Cabin in Edmunds Twp
4.86 out of 5 average rating, 109 reviewsCottage #3, Robinson's Cottages, Pet-friendly
Nov 3 – 10
Cottage in Milbridge
4.97 out of 5 average rating, 108 reviewsBayview Cottage on the Atlantic
Dec 10 – 17
Cottage in Beals
4.97 out of 5 average rating, 107 reviewsHarbor views + stylish interior + boat lounge
Apr 1 – 8
Family-friendly home rentals with a pool
Cottage in Belfast
4.58 out of 5 average rating, 12 reviewsShore Cottage
Apr 7 – 14
Home in South Thomaston
4.95 out of 5 average rating, 83 reviewsLarge private area, close to Rockland
Aug 22 – 29
Apartment in Stonington
4.92 out of 5 average rating, 12 reviewsThe Carriage House at Spruce Harbor
Jun 13 – 20
Home in Tremont
5.0 out of 5 average rating, 5 reviewsTremont, ME. Shorefront compound for 7-12
Sep 7 – 14
Apartment in Rockland
Heart of Rockland Maine
Nov 27 – Dec 4
Townhouse in Ellsworth
1 Bed Suite in a Resort near Acadia National Park
Jul 28 – Aug 4
Home in Lamoine
Close to Acadia National Park
Nov 2 – 9
Home in Stonington
Kate's House at Spruce Harbor
Sep 5 – 12
Quick stats about vacation rentals that are family-friendly in Winter Harbor
Total rentals
60 properties
Wifi availability
50 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
1.6K reviews
Nightly prices starting at
G$18,817 GYD before taxes and fees
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