Rent Luxury Accommodation for Groups in Connecticut

We selected the 48 homes worth renting in this location

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Home spotlights in Connecticut

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.

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

There are some homes that simply capture your heart from the moment you arrive. And we won’t be surprised if it’s love at first sight when you see this charming Colonial saltbox house.

Wisteria Delight

Wisteria Delight

  • 3 guests

  • 2 bedrooms

Springs, East Hampton

Escape to Springs, East Hamptons for a magical little visit to Wisteria Delight. The charming cottage sits on several acres of land and features a picturesque deck overgrown with wisteria, a private gunite pool, an outdoor fire pit and a large open floor plan.

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

Clued-up New Yorkers have slowly been turning their attention away from the Hamptons to this corner of countryside in Litchfield County. One step into this home, and we can see why they're making the swap.


We selected the top 3% holiday homes in Connecticut Accommodation for Groups

Explore the 48 most perfect homes in our collection

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Most popular homes in Connecticut

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Life As A Dream

Life As A Dream

  • 8 guests

  • 4 bedrooms

Montauk, East Hampton

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Number Nineteen

Number Nineteen

  • 13 guests

  • 6 bedrooms

Montauk, East Hampton

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

The Rainbow Bird

The Rainbow Bird

  • 8 guests

  • 4 bedrooms

Woodbury, Litchfield County

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Frequently asked questions

Reserve a stay in one of the impeccable homes in our collection of luxury Group Holiday Accommodation in Connecticut, United States. You won't find such consistent quality anywhere else, as every single Plum Guide home comes fully furnished with all linens, a brilliantly-equipped kitchen, and essential bathroom toiletries included. Our experts really do obsess over the smallest details, with shower pressure and a bedroom's decibel levels being tested to ensure absolute quality in your hunt for the perfect home. Rent Connecticut Accommodation for Groups today, and learn the true meaning of luxury. Call on our team of experts too, who can help you through the booking process and guarantee that you end up with the ultimate home for you.

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