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
4.9 out of 5 average rating, 144 reviewsWaterfront cottage overhanging the water!
Jan. 29 – Feb. 5
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
Cottage in Cutchogue
4.69 out of 5 average rating, 187 reviewsLovely 2 BR Beach House No. Shore
Dec. 17 – 24
Farm stay in Kent
4.87 out of 5 average rating, 263 reviews(°) The Wandering Peacock (°)
Jan. 30 – Feb. 6
Villa in Norwich
4.89 out of 5 average rating, 367 reviewsPeaceful Spa Escape minutes to Mohegan Sun Casino
Sep. 14 – 21
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
Oct. 31 – Nov. 7
Home in Stonington
4.97 out of 5 average rating, 185 reviewsPerfect New England Getaway has a pool/ hot tub
Mar. 2 – 9
Family- and pet-friendly home rentals
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
Dec. 22 – 29
Apartment in Middletown
4.9 out of 5 average rating, 240 reviews3 bedroom near Wesleyan, downtown
Sep. 26 – Oct. 3
Apartment in Glastonbury
4.9 out of 5 average rating, 409 reviewsQuiet 2 bed room apt w/ private entrance.
Feb. 8 – 15
Guest suite in Cutchogue
4.88 out of 5 average rating, 587 reviewsWalk to Vineyards, Beaches, Farms & Town
Aug. 12 – 19
Guest suite in Brooklyn
4.92 out of 5 average rating, 153 reviewsAffordable In-Law Apartment in Brooklyn, CT
Sep. 8 – 15
Guesthouse in Groton
4.94 out of 5 average rating, 385 reviewsQuiet studio with sleeping loft and deck
Sep. 2 – 9
Cabin in Voluntown
4.95 out of 5 average rating, 596 reviewsEllis -Lakeside Cabin on Beach Pond with Sauna
Nov. 24 – Dec. 1
Cottage in Riverhead
4.98 out of 5 average rating, 126 reviewsSavor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Jan. 3 – 10
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. 3 – 10
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Jul. 28 – Aug. 4
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Dec. 4 – 11
Home in East Hampton
4.93 out of 5 average rating, 140 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Sep. 30 – Oct. 7
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Oct. 25 – Nov. 1
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
Jul. 5 – 12
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep. 12 – 19
Guest suite in East Hampton
4.89 out of 5 average rating, 222 reviewsPrivate Cozy Cottage with Pool / Private Beach
Oct. 3 – 10
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
$137 CAD before taxes and fees
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