House vacation rentals in Middlesex County
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Top-rated house rentals in Middlesex County
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Middlesex County house rentals
House rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
Apr 15 – 22
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
Jun 25 – Jul 2
Home in Shelter Island
4.97 out of 5 average rating, 197 reviewsHuge Island Getaway Pool HotTub Walk To Beach
Dec 5 – 12
Home in Sag Harbor
4.89 out of 5 average rating, 166 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
Oct 18 – 25
Home in Manorville
4.99 out of 5 average rating, 201 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Oct 20 – 27
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Dec 31 – Jan 7
Home in East Hampton
4.93 out of 5 average rating, 141 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Dec 5 – 12
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Jul 19 – 26
Weekly house rentals
Home in Westbrook
5.0 out of 5 average rating, 27 reviewsSea Salt Air Changes Everything
Nov 20 – 27
Home in East Hampton
4.98 out of 5 average rating, 51 reviewsLake Fun: PingPong, Pool Table, Slide, EV Charger
Mar 10 – 17
Home in Madison
5.0 out of 5 average rating, 22 reviewsWriter's Retreat & Explorer's Adventure!
Sep 6 – 13
Home in Essex
4.97 out of 5 average rating, 35 reviewsIdeal Historic Home in Essex Village
Mar 29 – Apr 5
Home in Chester
4.98 out of 5 average rating, 50 reviewsTuscan Villa in Chester
Sep 16 – 23
Home in Clinton
5.0 out of 5 average rating, 18 reviewsSoundscape Beachfront House!
Sep 15 – 22
Home in East Hampton
4.95 out of 5 average rating, 21 reviewsWaterfront Lake House
Mar 19 – 26
Home in East Hampton
4.96 out of 5 average rating, 24 reviewsA Relaxing Getaway Lake House
Oct 12 – 19
Private house rentals
Home in Hebron
5.0 out of 5 average rating, 40 reviewsWelcome to The Avery!
Mar 27 – Apr 3
Home in Middletown
4.95 out of 5 average rating, 19 reviewsHot Tub and pool Home away from home
Nov 11 – 18
Home in Westbrook
5.0 out of 5 average rating, 38 reviewsHome Away From Home
Apr 8 – 15
Home in Old Saybrook
5.0 out of 5 average rating, 24 reviews3BR Private Cottage w/ Pool in Old Saybrook
Jan 15 – 22
Home in Essex
5.0 out of 5 average rating, 53 reviews4-Bedroom Farmhouse *Comfort and Privacy*
Jan 18 – 25
Home in Madison
5.0 out of 5 average rating, 17 reviewsNewly Renovated Beach Cottage!
Sep 11 – 18
Home in Madison
5.0 out of 5 average rating, 13 reviewsWaterfront Beach House with pool
Aug 25 – Sep 1
Home in Guilford
4.89 out of 5 average rating, 38 reviewsGuilford cozy in-law apt with private entrance
Sep 2 – 9
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