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
Get the amount of space that is right for you
Popular amenities for Middlesex County house rentals
House rentals with a pool
Home in Cutchogue
4.97 out of 5 average rating, 201 reviewsPrivate Oasis W/Stunning Vinyard and Pool Views
Home in Hampton Bays
4.94 out of 5 average rating, 121 reviewsPeaceful Retreat in Immaculate Architect’s House
Home in Cheshire
5 out of 5 average rating, 128 reviewsPool House
Home in East Hampton
4.94 out of 5 average rating, 155 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in Manorville
4.98 out of 5 average rating, 243 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in Montville
4.97 out of 5 average rating, 115 reviewsHot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos
Home in Cutchogue
4.98 out of 5 average rating, 131 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Home in East Hampton
4.98 out of 5 average rating, 128 reviewsExplore the Water & Woods at a Relaxing Retreat
Weekly house rentals
Home in Chester
4.8 out of 5 average rating, 64 reviewsCharmingly Chester on the Great Brook and Pond
Home in Colchester
4.89 out of 5 average rating, 19 reviewsHilltop Hideaway
Home in Essex
5 out of 5 average rating, 3 reviewsSunny Shores
Home in East Hampton
4.79 out of 5 average rating, 24 reviewsCharming River Home
Home in Madison
5 out of 5 average rating, 22 reviewsStylish Modern Home, 4-Bedroom, Madison CT
Home in Middletown
4.95 out of 5 average rating, 39 reviewsHot Tub and pool Home away from home
Home in Old Saybrook
5 out of 5 average rating, 28 reviewsSerene waterfront getaway 4Bd/2b
Home in Old Saybrook
5 out of 5 average rating, 37 reviewsGreat Hammcock Getaway, Nearby beaches, Hot tub
Private house rentals
Home in Westbrook
4.82 out of 5 average rating, 45 reviewsDuckling Crossing | Beach House on the Sand
Home in Old Lyme
4.98 out of 5 average rating, 55 reviewsRelax & Rejuvenate in this 1920s Riverfront Estate
Home in Old Saybrook
5 out of 5 average rating, 12 reviewsCornfield Point Beach House View
Home in East Hampton
4.93 out of 5 average rating, 14 reviewsLake House, Pet-Friendly
Home in East Hampton
5 out of 5 average rating, 25 reviewsThe Little Nest Cottage at Lake Pocotopaug
Home in Madison
4.87 out of 5 average rating, 23 reviewsHistoric Beachside Glamour
Home in Guilford
5 out of 5 average rating, 17 reviewsCoast and Country Private Estate
Home in East Hampton
4.92 out of 5 average rating, 91 reviewsPrivate home near Lake Pocotopaug!
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