Connecticut Guest Houses

We selected the 43 homes worth renting in this location

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Age 13+

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Children

Age 1 to 12

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Home spotlights in Connecticut

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.

Light of Romance

Light of Romance

  • 14 guests

  • 6 bedrooms

Springs, East Hampton

Find your own slice of heaven in East Hampton with a stay in this impressive glasshouse. Surrounded by lush trees with beautiful views, this is the perfect setting for a restorative retreat or special family gathering.

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.

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.


We selected the top 3% holiday homes in Connecticut Guest Houses

Explore the 43 most perfect homes in our collection

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Most popular homes in Connecticut

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Blissful Thinking

Blissful Thinking

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

High Tea & Hedgerows

High Tea & Hedgerows

  • 8 guests

  • 4 bedrooms

Pawling, New York

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Frequently asked questions

Looking for guesthouse style accommodation in Connecticut? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in the best guesthouse style accommodation that Connecticut has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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