Family-friendly vacation 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.
Vacation 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
4.92 out of 5 average rating, 202 reviewsLakeside cottage with beautiful views up the lake!
Dec 11 – 18
Cottage in Cutchogue
4.69 out of 5 average rating, 187 reviewsLovely 2 BR Beach House No. Shore
Apr 5 – 12
Home in Wading River
4.96 out of 5 average rating, 457 reviewsYour Zen Retreat
Jul 5 – 12
Guest suite in Mansfield
4.95 out of 5 average rating, 193 reviewsCozy private apt 8 mins from UCONN - solar powered
Oct 14 – 21
Home in Sag Harbor
4.89 out of 5 average rating, 166 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
May 3 – 10
Villa in Norwich
4.89 out of 5 average rating, 366 reviewsPeaceful Spa Escape minutes to Mohegan Sun Casino
Mar 1 – 8
Home in Stonington
4.97 out of 5 average rating, 185 reviewsPerfect New England Getaway has a pool/ hot tub
Dec 1 – 8
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Jan 8 – 15
Family- and pet-friendly home rentals
Apartment in Middletown
4.9 out of 5 average rating, 240 reviews3 bedroom near Wesleyan, downtown
Oct 13 – 20
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
Dec 22 – 29
Apartment in Glastonbury
4.9 out of 5 average rating, 409 reviewsQuiet 2 bed room apt w/ private entrance.
Dec 11 – 18
Guest suite in Brooklyn
4.92 out of 5 average rating, 153 reviewsAffordable In-Law Apartment in Brooklyn, CT
Apr 6 – 13
Guesthouse in Groton
4.94 out of 5 average rating, 385 reviewsQuiet studio with sleeping loft and deck
Sep 11 – 18
Farm stay in West Simsbury
4.95 out of 5 average rating, 430 reviewsFlamig Farm Staycation
Jan 25 – Feb 1
Cabin in Voluntown
4.95 out of 5 average rating, 596 reviewsEllis -Lakeside Cabin on Beach Pond with Sauna
Nov 24 – Dec 1
Guest suite in Fairfield
4.94 out of 5 average rating, 359 reviewsPrivate Studio Apartment; Kitchen; Fully Furnished
Jan 20 – 27
Family-friendly home rentals with a pool
Barn in Bethel
4.98 out of 5 average rating, 202 reviewsEscape to a Restored New England Antique Milk Barn
Sep 12 – 19
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Dec 3 – 10
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Aug 28 – Sep 4
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Oct 16 – 23
Home in East Hampton
4.93 out of 5 average rating, 140 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Nov 26 – Dec 3
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
Oct 12 – 19
Guest suite in East Hampton
4.89 out of 5 average rating, 222 reviewsPrivate Cozy Cottage with Pool / Private Beach
Oct 2 – 9
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Oct 25 – Nov 1
Quick stats about vacation 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
R1,881 ZAR before taxes and fees
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