Book Luxury Holiday Rentals in Connecticut

Award-winning homes from £98

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.

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.

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.


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

Explore the 140 most perfect homes in our collection

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Most popular homes in Connecticut

Modern Beach Retreat

Modern Beach Retreat

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

High Tea & Hedgerows

High Tea & Hedgerows

  • 8 guests

  • 4 bedrooms

Pawling, New York

An Old Fashioned

An Old Fashioned

  • 8 guests

  • 4 bedrooms

Napeague, East Hampton

Port & Starboard

Port & Starboard

  • 6 guests

  • 6 bedrooms

North Haven, Southampton

Artistic Sensibility

Artistic Sensibility

  • 8 guests

  • 3 bedrooms

East Hampton North, East Hampton

Paradise Cottage

Paradise Cottage

  • 9 guests

  • 4 bedrooms

Montauk, East Hampton

Star of the Show

Star of the Show

  • 6 guests

  • 3 bedrooms

Montauk, East Hampton

Number Nineteen

Number Nineteen

  • 13 guests

  • 6 bedrooms

Montauk, East Hampton

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Connecticut, United States. 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, United States 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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