Family-friendly vacation rentals in Middlesex County
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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
Guest suite in Mansfield
4.95 out of 5 average rating, 195 reviewsCozy private apt 8 mins from UCONN - solar powered
Jul 28 – Aug 4
Cottage in Southampton
4.96 out of 5 average rating, 164 reviewsSecluded Southampton Cottage w/Pool & Spa
Jan 25 – Feb 1
Cottage in Cutchogue
4.69 out of 5 average rating, 187 reviewsLovely 2 BR Beach House No. Shore
Apr 29 – May 6
Home in Sag Harbor
4.89 out of 5 average rating, 167 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
Oct 15 – 22
Villa in Norwich
4.89 out of 5 average rating, 367 reviewsPeaceful Spa Escape minutes to Mohegan Sun Casino
Aug 3 – 10
Home in Wading River
4.96 out of 5 average rating, 457 reviewsYour Zen Retreat
Aug 19 – 26
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
Nov 23 – 30
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsPrivate Oasis W/Stunning Vinyard And Pool Views
Mar 9 – 16
Family- and pet-friendly home rentals
Cottage in East Haddam
4.93 out of 5 average rating, 86 reviewsCottage on the hill
Jun 27 – Jul 4
Apartment in Branford
5.0 out of 5 average rating, 70 reviewsTree Fort Suite at Stony Creek Depot
Dec 6 – 13
Home in Old Saybrook
4.78 out of 5 average rating, 134 reviewsCapt Clarke Historic Homestead/Venue. Beaches,Pets
Feb 4 – 11
Home in East Hampton
4.77 out of 5 average rating, 52 reviewsMAGNIFICENT PRIVATE RIVERFRONT HOME, 10% off
Nov 13 – 20
Cottage in Guilford
4.93 out of 5 average rating, 231 reviewsThe Cottage at Indian Cove
Nov 4 – 11
Apartment in Old Saybrook
4.99 out of 5 average rating, 112 reviewsConvenient and Cute in Downtown Old Saybrook
Oct 18 – 25
Apartment in Deep River
4.76 out of 5 average rating, 54 reviewsSpacious 1-Bedroom Apartment surrounded by Woods
May 24 – 31
Cottage in Old Saybrook
5.0 out of 5 average rating, 79 reviewsCozy Waterfront Retreat
Dec 7 – 14
Family-friendly home rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
Mar 14 – 21
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
Jul 18 – 25
Bungalow in Montauk
4.91 out of 5 average rating, 531 reviewsMontauk Oceanview with Fireplace (2)
Dec 23 – 30
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Aug 29 – Sep 5
Guest suite in East Hampton
4.89 out of 5 average rating, 222 reviewsPrivate Cozy Cottage with Pool / Private Beach
Oct 10 – 17
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Sep 14 – 21
Home in East Hampton
4.93 out of 5 average rating, 141 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Nov 15 – 22
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Dec 2 – 9
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