Book Luxury Holiday Rentals in Connecticut

Award-winning homes from £98

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Age 13+

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Age 1 to 12

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Home spotlights in Connecticut

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, New York

Wander Inn is an architect-renovated ranch in a beautiful setting. Built in the sixties, this home is made for relaxation and indulgence.

Tucked In The Trees

Tucked In The Trees

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Get set to escape reality and embrace all things lavish and luxurious as you retreat to this sensational, mid–century East Hampton's home. Newly renovated and sat on 1.

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

At the bottom of the garden, you’ve got direct access to the serene waters of Noyack Bay, with kayaks, paddleboards and bicycles provided by your host. It’s a fifteen to twenty-minute walk (or five-minute cycle) to the restaurants and grocery store of Noyack, just along the coast from Sag Harbour.

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

A nature lover's dream atop a 100-acre historic farm in North Stonington, away from the hustle and bustle of everyday life. This home offers a one-of-a-kind stay – spend your mornings in the fresh air helping the hosts tend to the farm animals in the tranquil setting to feel at one with nature – from feeding chickens and collecting eggs to brushing the horses and rooster calls here and there, but it's all part of the experience.


We selected the top 3% holiday homes in Connecticut Holiday Rentals

Explore the 43 most perfect homes in our collection

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Most popular homes in Connecticut

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

High Tea & Hedgerows

High Tea & Hedgerows

  • 8 guests

  • 4 bedrooms

Pawling, New York

Hamlet

Hamlet

  • 8 guests

  • 5 bedrooms

Miller Place, Brookhaven

Walcott

Walcott

  • 8 guests

  • 3 bedrooms

Bridgehampton, Southampton

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Connecticut. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Connecticut has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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