Connecticut Guest Houses

We selected the 141 homes worth renting in this location

Home spotlights in Connecticut

Gatsby's Mansion

Gatsby's Mansion

  • 42 guests

  • 11 bedrooms

Belle Terre, Brookhaven

Homes like this are one in a million. An eight-acre complex on the Port Jefferson coastline, guests will find virtually everything they could wish for at the address.

The Fifties Barn

The Fifties Barn

  • 8 guests

  • 4 bedrooms

East Hampton, The Hamptons

Once a 1950s potato barn, this historic home now provides rustic charm in the affluent Hamptons. Though we fell in love with the loft library, dramatic furnishings, and leafy garden, complete with a private pool and hot tub, the location is also worth mentioning.

Well & Happy

Well & Happy

  • 10 guests

  • 5 bedrooms

Southold, The Hamptons

Just steps from the beach with views across Peconic Bay, this home brings ease and comfort to coastal living. Bikes are provided for exploring and it’s just a short drive to the restaurants and shops of Southold.

Saltbush

Saltbush

  • 7 guests

  • 4 bedrooms

Montauk, East Hampton

Located a short walk away from the beach, we thought Saltbush would be a great base for a family or a group of friends looking for a seaside escape. The decor has clean, simple, beachy vibe – it isn’t trying to be wildly innovative or elaborate, but it ties in well with the location, and the space feels comfortable and relaxing.


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

Explore the 141 most perfect homes in our collection

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Most popular homes in Connecticut

Meet Me In Montauk

Meet Me In Montauk

  • 6 guests

  • 4 bedrooms

Montauk, East Hampton

High Tea & Hedgerows

High Tea & Hedgerows

  • 8 guests

  • 4 bedrooms

Pawling, New York

Rock Around The Clock

Rock Around The Clock

  • 10 guests

  • 7 bedrooms

Bridgehampton, Southampton

The Dappled Light

The Dappled Light

  • 6 guests

  • 3 bedrooms

Springs, East Hampton

Ranch in the East

Ranch in the East

  • 8 guests

  • 4 bedrooms

Amagansett, East Hampton

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Paradise Cottage

Paradise Cottage

  • 9 guests

  • 4 bedrooms

Montauk, East Hampton

Number Nineteen

Number Nineteen

  • 13 guests

  • 6 bedrooms

Montauk, East Hampton

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Frequently asked questions

Looking for guesthouse style accommodation in Connecticut, United States? 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, United States has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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