Connecticut Guest Houses

We selected the 43 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in Connecticut

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.

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.

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

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

The Rainbow Bird

The Rainbow Bird

  • 8 guests

  • 4 bedrooms

Woodbury, Litchfield County

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

Blissful Thinking

Blissful Thinking

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

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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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