Family-friendly holiday rentals in Winthrop
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winthrop
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 Winthrop family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Waterford
4.83 out of 5 average rating, 217 reviewsMcWain pond house (private lake & hot tub)
10–17 Mar
Cabin in Appleton
4.88 out of 5 average rating, 276 reviewsRaven's Crossing - Kate's Cottage
10–17 Oct
Loft in Andover
4.98 out of 5 average rating, 154 reviewsPrivate studio loft, decks and hot tub
26 Nov – 3 Dec
Flat in Topsham
4.87 out of 5 average rating, 498 reviewsMaine Stay with private hottub, near Brunswick
17–24 Aug
Home in Bethel
4.96 out of 5 average rating, 124 reviewsWoodland Way Retreat- Hot Tub and Mountain Views!
16–23 Jul
Cottage in Chesterville
4.73 out of 5 average rating, 66 reviewsPrivate Lakefront Getaway in Central Maine
8–15 Jan
Cabin in Chesterville
4.86 out of 5 average rating, 43 reviewsLakefront Log Cabin-boats-fishing-swimming-hot tub
18–25 Sep
Home in Woodstock
4.85 out of 5 average rating, 88 reviewsLarge unique Lakefront with April discounts!
6–13 Nov
Family- and pet-friendly home rentals
Cabin in Skowhegan
4.82 out of 5 average rating, 401 reviewsThe Cabin -Skowhegan
28 Oct – 4 Nov
Cabin in Phillips
4.93 out of 5 average rating, 163 reviewsStream-side mountain retreat
4–11 Mar
Flat in Freeport
4.91 out of 5 average rating, 195 reviews1000 sq. ft. 1BR+ Apt Close to Town & Nature
5–12 Nov
Flat in Edgecomb
4.91 out of 5 average rating, 298 reviewsSunny Apt in Woods 10 Min to 3 Towns- Dog Friendly
29 Mar – 5 Apr
Farm stay in Gray
4.94 out of 5 average rating, 249 reviewsGreat Goat Get-away in Southern Maine!
20–27 Jan
Cabin in Carthage
4.94 out of 5 average rating, 182 reviewsPrivate Maine Camp
15–22 Nov
Cabin in Boothbay
4.93 out of 5 average rating, 179 reviewsPeaceful & private waterfront cabin
23–30 Oct
Cabin in Boothbay
4.95 out of 5 average rating, 402 reviewsSimple Boothbay Log Cabin on Water
4–11 Aug
Family-friendly home rentals with a pool
Flat in Brunswick
4.99 out of 5 average rating, 194 reviewsCharming Saltwater Farm apartment
17–24 Nov
Flat in Cornville
4.85 out of 5 average rating, 123 reviewsLarge Home with Great View next to horse farm
7–14 Jul
Tiny home in Harrison
4.9 out of 5 average rating, 280 reviewsMILLION$ views, HOT TUB, Crooked RIVER, 14 acres
25 Dec – 1 Jan
Home in Bridgton
4.89 out of 5 average rating, 152 reviewsMoose Pond Mountain Escape
2–9 Oct
Chalet in Frye Island
4.76 out of 5 average rating, 82 reviewsCabin in Paradise
17–24 Aug
Flat in Boothbay Harbor
5.0 out of 5 average rating, 27 reviewsLuxury Condo on Water's Edge in Boothbay Harbor
24–31 Mar
Home in Bethel
4.95 out of 5 average rating, 41 reviewsCaribou Run Private Retreat with Mountain Views
8–15 May
Home in Peru
4.95 out of 5 average rating, 210 reviewsthe lake house
12–19 Dec
Quick stats about holiday rentals that are family-friendly in Winthrop
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
720 reviews
Nightly prices starting at
₹10,860 before taxes and fees
Destinations to explore
- Portland Holiday rentals
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