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
Cabin in Appleton
4.88 out of 5 average rating, 277 reviewsRaven's Crossing - Kate's Cottage
31 Mar – 7 Apr
Home in Waterford
4.83 out of 5 average rating, 217 reviewsMcWain pond house (private lake & hot tub)
3–10 Jun
Apartment in Topsham
4.87 out of 5 average rating, 498 reviewsMaine Stay with private hottub, near Brunswick
6–13 Sep
Loft in Andover
4.98 out of 5 average rating, 154 reviewsPrivate studio loft, decks and hot tub
18–25 Apr
Home in Newry
4.96 out of 5 average rating, 109 reviewsThe Ridge House-Modern Chalet! Spectacular Views!
26 Nov – 3 Dec
Home in Portland
4.96 out of 5 average rating, 186 reviewsPeaceful Oasis with Water Views and Hot Tub!
15–22 Jan
Apartment in Falmouth
4.89 out of 5 average rating, 170 reviewsFalmouth 3br near Town landing
5–12 Jan
Home in Newry
4.95 out of 5 average rating, 149 reviewsBrownie- Comfy Modern Ranch Home w/Hot Tub
8–15 Apr
Family- and pet-friendly home rentals
Cabin in Skowhegan
4.82 out of 5 average rating, 401 reviewsThe Cabin -Skowhegan
3–10 Mar
Cabin in Dresden
4.96 out of 5 average rating, 157 reviewsMcKeen's Riverside Retreat
25 Sep – 2 Oct
Apartment in Edgecomb
4.91 out of 5 average rating, 298 reviewsSunny Apt in Woods 10 Min to 3 Towns- Dog Friendly
25 Jan – 1 Feb
Guest suite in Brunswick
4.93 out of 5 average rating, 315 reviewsArt House Gallery guest suite
16–23 Jan
Farm stay in Gray
4.94 out of 5 average rating, 249 reviewsGreat Goat Get-away in Southern Maine!
23–30 Jan
Apartment in Freeport
4.91 out of 5 average rating, 195 reviews1000 sq. ft. 1BR+ Apt Close to Town & Nature
13–20 Feb
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, 403 reviewsSimple Boothbay Log Cabin on Water
23–30 Oct
Family-friendly home rentals with a pool
Apartment in Brunswick
4.99 out of 5 average rating, 194 reviewsCharming Saltwater Farm apartment
26 Oct – 2 Nov
Apartment in Cornville
4.85 out of 5 average rating, 123 reviewsLarge Home with Great View next to horse farm
7–14 Aug
Tiny home in Harrison
4.9 out of 5 average rating, 280 reviewsMILLION$ views, HOT TUB, Crooked RIVER, 14 acres
2–9 Mar
Home in Bridgton
4.89 out of 5 average rating, 152 reviewsMoose Pond Mountain Escape
23–30 Aug
Chalet in Rangeley
4.86 out of 5 average rating, 159 reviewsA+ Views 2 Relax Write Hike Fish Boat Sunset/Stars
31 Dec – 7 Jan
Condo in Newry
4.94 out of 5 average rating, 101 reviewsSunday River Resort Condos @Cascades
15–22 May
Chalet in Frye Island
4.76 out of 5 average rating, 82 reviewsCabin in Paradise
17–24 Aug
Apartment in Boothbay Harbor
5.0 out of 5 average rating, 27 reviewsLuxury Condo on Water's Edge in Boothbay Harbor
12–19 Feb
Quick stats about holiday rentals that are family-friendly in Winthrop
Total rentals
30 properties
Wi-Fi availability
30 properties include access to Wi-Fi
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
$218 NZD before taxes and fees
Destinations to explore
- Portland Holiday rentals
- Bar Harbor Holiday rentals
- Old Orchard Beach Holiday rentals
- Lake Winnipesaukee Holiday rentals
- Ogunquit Holiday rentals
- Bangor Holiday rentals
- The Hamptons Holiday rentals
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- Québec City Holiday rentals
- Québec Holiday rentals
- Moncton Holiday rentals
- Family-friendly rentals United States
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