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, 120 reviewsPool House
Home in Montville
4.91 out of 5 average rating, 237 reviewsCasino Wine Down House***
Home in Shelter Island
4.97 out of 5 average rating, 205 reviewsHuge Island Getaway Pool HotTub Walk To Beach
Home in Manorville
4.99 out of 5 average rating, 208 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in Southampton
4.91 out of 5 average rating, 100 reviewsSerene 3 Bed 2.5 Bath House w/Heated Pool
Home in Southampton
4.95 out of 5 average rating, 133 reviewsWaterview, Pool, DogsStayFree! Kayaks, PingPong
Home in East Hampton
4.92 out of 5 average rating, 131 reviewsHeated pool, games room, near beach, kid-friendly
Home in Cutchogue
4.96 out of 5 average rating, 191 reviewsPrivate Oasis Stunning Views 7/6 - 7/20 Available
Weekly house rentals
Home in Old Saybrook
4.96 out of 5 average rating, 50 reviewsSteps to Beach! *Cozy Cottage* Pet Friendly
Home in Essex
5.0 out of 5 average rating, 21 reviewsPrivate Escape Bedroom Suite & Firepit
Home in Haddam
5.0 out of 5 average rating, 11 reviewsThe Farmhouse Stay
Home in Guilford
4.95 out of 5 average rating, 22 reviewsTiny home one block from the town green.
Home in East Hampton
4.98 out of 5 average rating, 54 reviewsLake Fun: PingPong, Pool Table, Slide, EV Charger
Home in Hebron
5.0 out of 5 average rating, 46 reviewsWelcome to The Avery!
Home in Middletown
4.95 out of 5 average rating, 21 reviewsHot Tub and pool Home away from home
Home in Essex
4.97 out of 5 average rating, 36 reviewsIdeal Historic Home in Essex Village
Private house rentals
Home in Old Saybrook
5.0 out of 5 average rating, 5 reviewsRomantic Couples Retreat with Private Sandy Beach
Home in Madison
5.0 out of 5 average rating, 17 reviewsNewly Renovated Beach Cottage!
Home in Westbrook
4.89 out of 5 average rating, 19 reviewsPrivate vacation home, close to beach
Home in Madison
5.0 out of 5 average rating, 26 reviewsWriter's Retreat & Explorer's Adventure!
Home in East Haddam
4.97 out of 5 average rating, 34 reviewsCloud 9 - Guest favorite! Pool, hot tub, game room
Home in Madison
5.0 out of 5 average rating, 14 reviewsWaterfront Beach House with pool
Home in Chester
4.98 out of 5 average rating, 52 reviewsTuscan Villa in Chester
Home in Old Lyme
5.0 out of 5 average rating, 19 reviews5* 5 bed Luxury CT beach for large groups/families
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