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Family-friendly holiday houses in Winslow
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winslow
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winslow family-friendly rentals
Family-friendly home rentals with a hot tub
![](https://a0.muscache.com/im/pictures/202a3025-b276-4b14-8835-142dc8731c56.jpg?im_w=720)
Rental unit in Searsport
4.82 out of 5 average rating, 296 reviewsLakefront Vacation Apartment in Searsport ME
![](https://a0.muscache.com/im/pictures/4d563cc4-5284-4ff0-8778-1e90e017dc7d.jpg?im_w=720)
Cabin in Appleton
4.89 out of 5 average rating, 282 reviewsRaven's Crossing - Kate's Cottage
![](https://a0.muscache.com/im/pictures/9a1ec932-ad60-44c6-aa6c-9a54a7dfb721.jpg?im_w=720)
Chalet in Carrabassett Valley
4.98 out of 5 average rating, 117 reviewsHot tub! Outdoor paradise! PAC-MAN! Hiking&Biking!
![](https://a0.muscache.com/im/pictures/4a9a21d4-f350-432f-bf36-fbe823a40779.jpg?im_w=720)
Cottage in Verona Island
4.89 out of 5 average rating, 157 reviewsNashport on the Penobscot
![](https://a0.muscache.com/im/pictures/8d58aa11-ec0c-4906-96b5-13167373224a.jpg?im_w=720)
Rental unit in Topsham
4.87 out of 5 average rating, 501 reviewsMaine Stay with private hottub, near Brunswick
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Home in Holden
4.96 out of 5 average rating, 215 reviewsChalet Central
![](https://a0.muscache.com/im/pictures/a00fdb67-e8d9-46a3-a8c6-0482854784e9.jpg?im_w=720)
Cabin in Chesterville
4.86 out of 5 average rating, 43 reviewsLakefront Log Cabin-secluded-boats-fishing-hot tub
![](https://a0.muscache.com/im/pictures/6774133d-5221-470d-a59a-290fa0f8b202.jpg?im_w=720)
Cottage in Chesterville
4.73 out of 5 average rating, 66 reviewsPrivate Lakefront Getaway in Central Maine
Family- and pet-friendly home rentals
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Cabin in Nobleboro
4.94 out of 5 average rating, 108 reviewsWaterside Cabin the Woods 50 acres-No hidden fees!
![](https://a0.muscache.com/im/pictures/miso/Hosting-8014196/original/e5f90036-4fe6-4f3f-bdf1-03b474190579.jpeg?im_w=720)
Cabin in Weld
4.98 out of 5 average rating, 160 reviewsColby's Cabin
![](https://a0.muscache.com/im/pictures/3126594/0787a353_original.jpg?im_w=720)
Cabin in Boothbay
4.93 out of 5 average rating, 184 reviewsPeaceful & private waterfront cabin
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Rental unit in Edgecomb
4.91 out of 5 average rating, 301 reviewsSunny Apt in Woods 10 Min to 3 Towns- Dog Friendly
![](https://a0.muscache.com/im/pictures/1a67eb99-3a03-4dbe-be31-e4cf13f65375.jpg?im_w=720)
Home in Stetson
4.96 out of 5 average rating, 155 reviewsLakefront Log Cabin on Pleasant Lake
![](https://a0.muscache.com/im/pictures/b3838428-e400-44fa-a8d1-33313c82219d.jpg?im_w=720)
Rental unit in Lisbon falls
4.95 out of 5 average rating, 393 reviewsCharming Victorian farmhouse 1880's bedrooms-2
![](https://a0.muscache.com/im/pictures/7b3ad87c-73c1-494a-9c3c-4010445769fb.jpg?im_w=720)
Farm stay in Gray
4.94 out of 5 average rating, 253 reviewsGreat Goat Get-away in Southern Maine!
![](https://a0.muscache.com/im/pictures/d3363ee5-b894-4c52-86e3-ddbdd523157f.jpg?im_w=720)
Cabin in Boothbay
4.95 out of 5 average rating, 406 reviewsSimple Boothbay Log Cabin on Water
Family-friendly home rentals with a pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-14009061/original/a82b1d43-c9f1-494d-b051-3a66effe7ff4.jpeg?im_w=720)
Tiny home in Harrison
4.9 out of 5 average rating, 280 reviewsMillion $ views, Hot Tub, Waterfront, 14 acres WOW
![](https://a0.muscache.com/im/pictures/107738019/2fb626ad_original.jpg?im_w=720)
Rental unit in Brunswick
4.99 out of 5 average rating, 197 reviewsCharming Saltwater Farm apartment
![](https://a0.muscache.com/im/pictures/cb3b48da-daf5-4b7d-a181-2dec19e37f9c.jpg?im_w=720)
Rental unit in Cornville
4.86 out of 5 average rating, 125 reviewsLarge Home with Great View next to horse farm
![](https://a0.muscache.com/im/pictures/04c1acbb-fd6d-4418-8dc4-995d020571c7.jpg?im_w=720)
Chalet in Rangeley
4.86 out of 5 average rating, 161 reviewsA+ Views 2 Relax Write Hike Fish Boat Sunset/Stars
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Chalet in Frye Island
4.76 out of 5 average rating, 82 reviewsCabin in Paradise
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Rental unit in Boothbay Harbor
5 out of 5 average rating, 28 reviewsLuxury Condo on Water's Edge in Boothbay Harbor
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Cottage in Belfast
4.58 out of 5 average rating, 12 reviewsShore Cottage
![](https://a0.muscache.com/im/pictures/e979f4b8-ef44-4104-86a6-78e45047b093.jpg?im_w=720)
Home in South Thomaston
4.95 out of 5 average rating, 85 reviewsLarge private area, close to Rockland
Quick stats about accommodation & holiday rentals that are family-friendly in Winslow
Total rentals
20 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
20 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
630 reviews
Nightly prices starting at
$45 AUD before taxes and fees
Destinations to explore
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- Family-friendly rentals United States
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