House holiday 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.
Holiday rentals for every style
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Popular amenities for Middlesex County house rentals
House rentals with a pool
Home in Montville
4.91 out of 5 average rating, 251 reviewsCasino Wine Down House***
Home in Cutchogue
4.96 out of 5 average rating, 198 reviewsPrivate Oasis W/Stunning Vinyard and Pool Views
Home in Hampton Bays
4.94 out of 5 average rating, 119 reviewsPeaceful Retreat in Immaculate Architect’s House
Home in Cheshire
5 out of 5 average rating, 125 reviewsPool House
Home in Manorville
4.98 out of 5 average rating, 239 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in Montville
4.97 out of 5 average rating, 110 reviewsHot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos
Home in Cutchogue
4.98 out of 5 average rating, 124 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Home in Sag Harbor
4.85 out of 5 average rating, 257 reviewsExclusive Sag Harbor Compound
Weekly house rentals
Home in Chester
4.79 out of 5 average rating, 63 reviewsCharmingly Chester on the Great Brook and Pond
Home in Madison
5 out of 5 average rating, 12 reviewsBeach Home & Garden Paradise
Home in Guilford
5 out of 5 average rating, 20 reviewsCharming 2BR Beach House Overlooking the Water
Home in Old Saybrook
4.94 out of 5 average rating, 47 reviewsWater Views and Walk to Beach
Home in Middletown
4.95 out of 5 average rating, 38 reviewsHot Tub and pool Home away from home
Home in Old Saybrook
4.7 out of 5 average rating, 209 reviewsThe Cottage
Home in Haddam
5 out of 5 average rating, 76 reviewsAutumn at The Haddam House
Home in Clinton
4.95 out of 5 average rating, 96 reviewsTreasured 1924 Colonial "Sweet Caroline"
Private house rentals
Home in East Hampton
4.86 out of 5 average rating, 92 reviewsBeautiful Lake House on Lake Pocotopaug
Home in Essex
5 out of 5 average rating, 3 reviewsSunny Shores
Home in Old Saybrook
5 out of 5 average rating, 11 reviewsCornfield Point Beach House View
Home in Madison
4.75 out of 5 average rating, 4 reviewsSea La Vie - Beachfront by BellaView Designs
Home in East Hampton
4.77 out of 5 average rating, 22 reviewsCharming River Home
Home in Old Saybrook
5 out of 5 average rating, 34 reviewsGreat Hammcock Getaway, Nearby beaches, Hot tub
Home in Clinton
4.78 out of 5 average rating, 40 reviewsLONG-TERM Glass House-Fall/Beach 5mins/Ski 25mins
Home in East Hampton
4.93 out of 5 average rating, 90 reviewsPrivate home near Lake Pocotopaug!
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