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
Get the amount of space that is right for you
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 1 – 8
Home in Montville
4.96 out of 5 average rating, 106 reviewsCasino Stay & Play House
Jun 3 – 10
Home in Manorville
4.99 out of 5 average rating, 200 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Oct 13 – 20
Home in Sag Harbor
4.89 out of 5 average rating, 166 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
Sep 24 – Oct 1
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Aug 7 – 14
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Feb 24 – Mar 3
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
Dec 30 – Jan 6
Home in Southampton
4.87 out of 5 average rating, 237 reviewsSecluded Southampton Luxury Estate with tennis 288
Dec 24 – 31
Weekly house rentals
Home in Haddam
5.0 out of 5 average rating, 9 reviewsThe Farmhouse Stay
Jun 8 – 15
Home in Madison
5.0 out of 5 average rating, 22 reviewsWriter's Retreat & Explorer's Adventure!
Dec 10 – 17
Home in Chester
4.98 out of 5 average rating, 50 reviewsTuscan Villa in Chester
May 13 – 20
Home in Essex
4.97 out of 5 average rating, 35 reviewsIdeal Historic Home in Essex Village
Mar 27 – Apr 3
Home in East Haddam
4.95 out of 5 average rating, 96 reviewsRomantic Getaway at The Lake!
Oct 5 – 12
Home in East Hampton
4.98 out of 5 average rating, 51 reviewsLake Fun: PingPong, Pool Table, Slide, EV Charger
Jan 7 – 14
Home in East Hampton
4.96 out of 5 average rating, 24 reviewsA Relaxing Getaway Lake House
May 13 – 20
Home in Essex
5.0 out of 5 average rating, 24 reviews3-Bedroom Farmhouse, Essex CT
Jun 4 – 11
Private house rentals
Home in East Hampton
4.99 out of 5 average rating, 92 reviewsClassic Lake House~4 Steps to water_FirePit_kayaks
Nov 20 – 27
Home in Middletown
4.95 out of 5 average rating, 19 reviewsHot Tub and pool Home away from home
Jul 31 – Aug 7
Home in East Haddam
5.0 out of 5 average rating, 15 reviewsPine Pond at Devils Hopyard State Park
Jun 4 – 11
Home in Clinton
5.0 out of 5 average rating, 18 reviewsSoundscape Beachfront House!
Sep 25 – Oct 2
Home in Old Lyme
5.0 out of 5 average rating, 17 reviews5* 5 bed Luxury CT beach for large groups/families
Dec 17 – 24
Home in East Hampton
4.95 out of 5 average rating, 21 reviewsWaterfront Lake House
Feb 16 – 23
Home in Westbrook
5.0 out of 5 average rating, 27 reviewsSea Salt Air Changes Everything
Dec 16 – 23
Home in Madison
5.0 out of 5 average rating, 17 reviewsNewly Renovated Beach Cottage!
Sep 7 – 14
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