Family-friendly vacation rentals in Middlesex County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Middlesex County
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Middlesex County family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Cutchogue
4.97 out of 5 average rating, 201 reviewsPrivate Oasis W/Stunning Vinyard and Pool Views
Guest suite in Mansfield
4.96 out of 5 average rating, 201 reviewsCozy private apt 8 mins from UCONN - solar powered
Home in Wading River
4.96 out of 5 average rating, 488 reviewsYour Zen Retreat
Cottage in Southampton
4.96 out of 5 average rating, 176 reviewsSecluded Southampton Cottage w/Pool & Spa
Home in Southampton
5 out of 5 average rating, 11 reviewsHamptons Modern Retreat NEW CONS
Home in Southampton
4.83 out of 5 average rating, 210 reviewsCozy & Chic Summer Getaway near village/beaches
Villa in Norwich
4.89 out of 5 average rating, 383 reviewsPeaceful Spa Escape minutes to Mohegan Sun Casino
Home in Greenport
4.93 out of 5 average rating, 451 reviewsBlue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
Family- and pet-friendly home rentals
Home in East Hampton
4.77 out of 5 average rating, 52 reviewsMAGNIFICENT PRIVATE RIVERFRONT HOME, 10% off
Home in Guilford
4.97 out of 5 average rating, 65 reviewsShoreline Cottage by Beach; Birder's Paradise
Rental unit in Guilford
5 out of 5 average rating, 5 reviewsLakefront Country Oasis
Home in Deep River
4.53 out of 5 average rating, 38 reviewsPeace Barn in the heart of the CT River Valley
Home in Guilford
4.71 out of 5 average rating, 123 reviewsPurple Button Factory Sleeps 6 Walk to Town Green
Home in Old Saybrook
4.95 out of 5 average rating, 41 reviewsEscape to our Waterfront House In Old Saybrook CT
Rental unit in Glastonbury
4.9 out of 5 average rating, 423 reviewsQuiet 2 bed room apt w/ private entrance.
Home in Lyme
4.9 out of 5 average rating, 91 reviewsLuxurious country guest house
Family-friendly home rentals with a pool
Home in Montville
4.91 out of 5 average rating, 254 reviewsCasino Wine Down House***
Home in New London
4.91 out of 5 average rating, 175 reviewsSunset Oasis @ Ocean Beach: $1Mil View w/ 6 Queen
Home in East Hampton
4.93 out of 5 average rating, 107 reviewsPrivate & Pristine with Pool and Kid’s Playard
Home in Hampton Bays
4.94 out of 5 average rating, 121 reviewsPeaceful Retreat in Immaculate Architect’s House
Home in Sag Harbor
4.81 out of 5 average rating, 134 reviewsThanksgiving! Sag Harbor Gem!
Home in Cheshire
5 out of 5 average rating, 128 reviewsPool House
Home in Southampton
4.94 out of 5 average rating, 270 reviewsSouthampton Village Classic-Summer Special!
Home in East Hampton
4.94 out of 5 average rating, 155 reviews1800 Historical East Hampton Home, 1 Mile to Town!
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