Book Luxury Vacation Rentals with a Private Chef in Connecticut

We selected the 43 homes worth renting in this location

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Home spotlights in Connecticut

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Arriving at this effortlessly chic seaside home from the city is a shockingly swift affair – you can be in Manhattan for breakfast and Sag Harbour for lunch. With its white-washed interiors and beachy accents, the home is ideal for a family of weekenders or those looking for a long-term change of scenery.

The Old Silo

The Old Silo

  • 4 guests

  • 2 bedrooms

Litchfield, Northwest Hills Planning Region

Formerly a grain silo, this extraordinary house is as unique and beautiful as its surroundings. Set on 170 acres of rolling green New England countryside, there are breathtaking views from all sides.

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

For the ultimate Montauk escape with style and character in abundance, this fisherman's cottage has you covered. Flamingo-pink shutters and the front door set the scene for a stay that's thoughtfully stylish, charming and quirky – a blend of boho and rustic that's sophisticated and easy to love.

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, and John Steinbeck.


We selected the top 3% holiday homes in Connecticut Vacation Rentals with a Private Chef

Explore the 43 most perfect homes in our collection

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Most popular homes in Connecticut

Valley Echo

Valley Echo

  • 4 guests

  • 2 bedrooms

Falls Village, Canaan

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Walcott

Walcott

  • 8 guests

  • 3 bedrooms

Bridgehampton, Southampton

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

Hamlet

Hamlet

  • 8 guests

  • 5 bedrooms

Miller Place, Brookhaven

Doric Detail

Doric Detail

  • 8 guests

  • 4 bedrooms

Dover, Dutchess County

Magic in The Hamptons

Magic in The Hamptons

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

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Frequently asked questions

Explore our unbeatable collection of luxury Vacation Rentals with a Personal Chef in Connecticut. Each and every home in our range comes fully furnished with excellently-equipped kitchens, essential bathroom toiletries, and all necessary linens included. Tested aspects of any home range from Wifi speed and shower pressure to a space's feel and design, so there really is nothing left to chance on our mission to discover the greatest properties on offer. Enjoy a stay in one of the Holiday Rentals in Connecticut with a Private Chef today, and remember your trip for all the right reasons. And don't hesitate to contact our team of experts if you require any assistance, as it is their pleasure to help make the process easy.

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