Book Luxury Holiday Rentals in Connecticut

Award-winning homes from £98

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Home spotlights in Connecticut

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

The summer retreat for Manhattan’s wealthy elite, the vibe of the Hamptons couldn’t be further from New York’s chaotic urban sprawl. And if you’re looking for the ultimate in serenity and tranquility, this idyllic beach house is for you.

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

If you’re looking for all the charm of a country cottage with the space and grandeur of a manor house, this is the spot for you. It’s a four-minute stroll to the vast stretch of sand at Long Beach and a six-minute drive sees you in the heart of the pretty village of Sag Harbor.

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.

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Just steps away from a private community beach, Borne Back was designed by its architect owner to provide a comfortable contemporary home in a perfectly quiet spot in the Hamptons. On a full acre plot next to Gardiner's Bay, it's surrounded by tall trees.


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

Explore the 43 most perfect homes in our collection

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Most popular homes in Connecticut

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

Doric Detail

Doric Detail

  • 8 guests

  • 4 bedrooms

Dover, Dutchess County

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Northwest Hills Planning Region

Mahogany

Mahogany

  • 6 guests

  • 3 bedrooms

Amenia, Dutchess County

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Frequently asked questions

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