Book Luxury Holiday Rentals in Connecticut

Award-winning homes from £98

Home spotlights in Connecticut

Life As A Dream

Life As A Dream

  • 8 guests

  • 4 bedrooms

Montauk, East Hampton

Whether it's alfresco dining, sun lounging or sitting around the fire pit at sunset, this beautiful house has seating for almost every occasion. And found only five minutes from the beach, it's calling on sun worshippers everywhere to come and enjoy the drop-your-bags-and-go proximity.

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.

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, and John Steinbeck.

High Tea & Hedgerows

High Tea & Hedgerows

  • 8 guests

  • 4 bedrooms

Pawling, New York

This home sits pretty as an English manor in the countryside of upstate New York, a ten-minute drive from the picturesque town of Pawling. Grecian-style columns greet you on arrival and the striking white facade glows against the verdant green gardens – it sits on 18 acres of land.


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

Explore the 51 most perfect homes in our collection

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Most popular homes in Connecticut

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Magic in The Hamptons

Magic in The Hamptons

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Wisteria Delight

Wisteria Delight

  • 3 guests

  • 2 bedrooms

Springs, 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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