Book Luxury Holiday Rentals in Connecticut

Award-winning homes from £98

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Adults

Age 13+

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Children

Age 1 to 12

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Home spotlights in Connecticut

Hamlet

Hamlet

  • 8 guests

  • 5 bedrooms

Miller Place, Brookhaven

An understated colonial-style home is the perfect setting for a Northeastern getaway. It's reminiscent of a family heirloom, with history seeping through the walls.

Walcott

Walcott

  • 8 guests

  • 3 bedrooms

Bridgehampton, Southampton

With a swimming pool outside and a huge playroom inside, there's no chance of boredom at this Hamptons retreat. Set in luscious forest near Bridgehampton and Sag Harbor, you're a short drive from shops, restaurants, and activities, while being secluded in your own peaceful bubble.

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

A luxurious harbour-front villa overlooking the serene Noyack Bay, this home's stylish interior boasts elegance and sophistication. Huge, panoramic windows display the beautiful surroundings while flooding the space with light.

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

For the ultimate Montauk escape with style and character in abundance, this fisherman's cottage has you covered. Flamingo-pink shutters and the front door set the scene for a stay that's thoughtfully stylish, charming and quirky – a blend of boho and rustic that's sophisticated and easy to love.


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

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Northwest Hills Planning Region

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

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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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