Book Luxury Airbnb Alternatives in Connecticut

We selected the 43 homes worth renting in this location

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Home spotlights in Connecticut

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Exploring East Hampton is a breeze at this coastal cottage. Both downtown and the beach are easily accessible by bike, and a coffee shop and seafood restaurant are just down the street.

The Old Silo

The Old Silo

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

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.

Doric Detail

Doric Detail

  • 8 guests

  • 4 bedrooms

Dover, Dutchess County

Originally built in the 1870s, this farmhouse has been added to over time to create a sociable family home. Inside, original details such as exposed wooden beams and large sash windows are complemented by vintage furniture and traditional furnishings, while a bar is ideal for evening cocktails.

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 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, Nora Ephron and John Steinbeck.


We selected the top 3% holiday homes in Connecticut Airbnb Alternatives

Explore the 43 most perfect homes in our collection

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Most popular homes in Connecticut

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

High Tea & Hedgerows

High Tea & Hedgerows

  • 8 guests

  • 4 bedrooms

Pawling, New York

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Blissful Thinking

Blissful Thinking

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

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Frequently asked questions

Airbnb is a shot in the dark. We meticulously vet all our homes in Connecticut to ensure you won’t waste your precious holiday. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury Connecticut Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.

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