Family-friendly holiday rentals in Madison
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Madison
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 Madison family-friendly rentals
Family-friendly home rentals with a hot tub
Cottage in Ledyard
4.9 out of 5 average rating, 146 reviewsWaterfront cottage overhanging the water!
2 – 9 Dec
Home in Wading River
4.96 out of 5 average rating, 457 reviewsYour Zen Retreat
5 – 10 May
Home in Sag Harbor
4.89 out of 5 average rating, 166 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
19 – 26 Oct
Guest suite in Mansfield
4.95 out of 5 average rating, 193 reviewsCozy private apt 8 mins from UCONN - solar powered
6 – 13 Oct
Villa in Norwich
4.89 out of 5 average rating, 367 reviewsPeaceful Spa Escape minutes to Mohegan Sun Casino
30 July – 6 Aug
Home in Center Moriches
4.98 out of 5 average rating, 189 reviewsWalk to beach and playground. Outdoor hot tub.
14 – 21 Oct
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
6 – 13 Mar
Home in Stonington
4.97 out of 5 average rating, 185 reviewsPerfect New England Getaway has a pool/ hot tub
21 – 28 Mar
Family- and pet-friendly home rentals
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
21 – 28 May
Apartment in Glastonbury
4.9 out of 5 average rating, 409 reviewsQuiet 2 bed room apt w/ private entrance.
19 – 26 Dec
Apartment in Middletown
4.9 out of 5 average rating, 241 reviews3 bedroom near Wesleyan, downtown
27 July – 3 Aug
Guest suite in Brooklyn
4.92 out of 5 average rating, 153 reviewsAffordable In-Law Apartment in Brooklyn, CT
20 – 27 Feb
Guest suite in Waterbury
4.94 out of 5 average rating, 250 reviewsPrivate 1 bedroom apartment in central Connecticut
25 Nov – 2 Dec
Guesthouse in Groton
4.94 out of 5 average rating, 385 reviewsQuiet studio with sleeping loft and deck
13 – 20 Aug
Cabin in Voluntown
4.95 out of 5 average rating, 597 reviewsEllis -Lakeside Cabin on Beach Pond with Sauna
24 Nov – 1 Dec
Guest suite in Fairfield
4.94 out of 5 average rating, 361 reviewsPrivate Studio Apartment; Kitchen; Fully Furnished
27 Jan – 3 Feb
Family-friendly home rentals with a pool
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
12 – 19 Sept
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
20 – 27 Aug
Barn in Bethel
4.98 out of 5 average rating, 203 reviewsEscape to a Restored New England Antique Milk Barn
29 Dec – 5 Jan
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
4 – 11 Sept
Home in East Hampton
4.93 out of 5 average rating, 141 reviews1800 Historical East Hampton Home, 1 Mile to Town!
15 – 22 Jan
Guest suite in East Hampton
4.89 out of 5 average rating, 222 reviewsPrivate Cozy Cottage with Pool / Private Beach
10 – 17 Oct
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
20 – 27 Dec
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
19 – 26 July
Quick stats about holiday rentals that are family-friendly in Madison
Total rentals
80 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Total number of reviews
1.6K reviews
Nightly prices starting at
$151 AUD before taxes and fees
Destinations to explore
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