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

Blissful Thinking

Blissful Thinking

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Experience the Hamptons in all of its heyday glory with a stay at Blissful Thinking. The former homestead and summer camp embodies one of the last wild spaces in the Hamptons, nestled right by the water's edge and facing Gardiner's Island.

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

If you’re looking for all the charm of a country cottage with the space and grandeur of a manor house, this is the spot for you. It’s a four-minute stroll to the vast stretch of sand at Long Beach and a six-minute drive sees you in the heart of the pretty village of Sag Harbor.

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Sea Aster sits in an ideal spot for exploring beach and town life. Sag Harbor Main Street, with its restaurants, boutiques and artisan bakeries, is less than fifteen minutes’ walk away, and you can get to Haven’s Beach – a perfect spot to watch the sun set – in ten.

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.


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

The Old Silo

The Old Silo

  • 4 guests

  • 2 bedrooms

Litchfield, Northwest Hills Planning Region

Mahogany

Mahogany

  • 6 guests

  • 3 bedrooms

Amenia, Dutchess County

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Walcott

Walcott

  • 8 guests

  • 3 bedrooms

Bridgehampton, Southampton

Valley Echo

Valley Echo

  • 4 guests

  • 2 bedrooms

Falls Village, Canaan

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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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