Connecticut Chalets

We selected the 43 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Connecticut

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

There are some homes that simply capture your heart from the moment you arrive. And we won’t be surprised if it’s love at first sight when you see this charming Colonial saltbox house.

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.

Magic in The Hamptons

Magic in The Hamptons

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

This beautiful home is set within dense woodland on the northern East Hampton Coast, just two blocks from a private beach looking out over Gardiners Bay. Inside, there are beautiful hardwood floors, a cosy fireplace for cool evenings and cathedral-like ceilings over the dining area.

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

This colourful Hamptons home has a laid back, friendly feel that would be perfect for a group of friends or family. In a quiet part of the Northwest Woods area of East Hampton, the house is surrounded by trees which guarantees peace, quiet and privacy to enjoy your trip.


We selected the top 3% holiday homes in Connecticut Chalets

Explore the 43 most perfect homes in our collection

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Most popular homes in Connecticut

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Mahogany

Mahogany

  • 6 guests

  • 3 bedrooms

Amenia, Dutchess County

High Tea & Hedgerows

High Tea & Hedgerows

  • 8 guests

  • 4 bedrooms

Pawling, New York

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Light of Romance

Light of Romance

  • 14 guests

  • 6 bedrooms

Springs, East Hampton

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

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Frequently asked questions

A chalet in Connecticut is the perfect accommodation for a cosy holiday. Find your dream one by browsing Plum Guide’s collection of homes. They come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the most charming chalets that Connecticut has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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