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 East Hampton
4.95 out of 5 average rating, 60 reviewsCountry getaway - huge yard, pool
Home in Old Saybrook
5 out of 5 average rating, 13 reviewsBeautiful Shoreline home in parklike setting
Home in Old Lyme
4.7 out of 5 average rating, 10 reviewsGorgeous 1700s Home Sleeps 10, 3 bath, Pool
Home in East Hampton
5 out of 5 average rating, 4 reviewsDirect riverfront luxury home!
Home in Clinton
4.96 out of 5 average rating, 28 reviewsNEW! 5-bedroom historic cottage, near beach
Home in Killingworth
4.75 out of 5 average rating, 4 reviewsQuiet Connecticut Retreat w/ Pool, Deck & Fire Pit
Home in Middletown
4.95 out of 5 average rating, 39 reviewsHot Tub and pool Home away from home
Home in East Hampton
4.83 out of 5 average rating, 6 reviewsCountry escape w/pool, waterfall - 2h NYC/Boston
Weekly house rentals
Home in Guilford
4.82 out of 5 average rating, 28 reviewsGuilford Home self check-in & off street parking
Home in Old Lyme
4.94 out of 5 average rating, 266 reviewsModern Luxurious CT Country Home
Home in Westbrook
4.85 out of 5 average rating, 182 reviewsFamily-Friendly Cottage by The Shore
Home in Middletown
4.88 out of 5 average rating, 294 reviewsHistoric Greek Revival Brick Home
Home in East Hampton
4.73 out of 5 average rating, 26 reviewsCharming River Home
Home in Madison
5 out of 5 average rating, 22 reviewsStylish Modern Home, 4-Bedroom, Madison CT
Home in Essex
4.96 out of 5 average rating, 69 reviews4-Bedroom Farmhouse *Comfort and Privacy*
Home in Madison
4.87 out of 5 average rating, 23 reviewsHistoric Beachside Glamour
Private house rentals
Home in Guilford
4.87 out of 5 average rating, 47 reviewsThe Davis House
Home in Haddam
4.97 out of 5 average rating, 78 reviewsAutumn at The Haddam House
Home in Clinton
4.96 out of 5 average rating, 25 reviewsZaku’s Lake House
Home in Guilford
5 out of 5 average rating, 17 reviewsCoast and Country Private Estate
Home in Essex
4.94 out of 5 average rating, 18 reviewsHyde House-A classic New England cape.
Home in Old Saybrook
5 out of 5 average rating, 3 reviewsFenwood Coastal Getaway Private Beach Access
Home in Clinton
4.79 out of 5 average rating, 43 reviewsLONG-TERM Glass House-Fall/Beach 5mins/Ski 25mins
Home in Guilford
5 out of 5 average rating, 24 reviewsEntire home - Cheerful 4 bedroom on the shoreline.
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