Rent Luxury Holiday Cottages in Connecticut

We selected the 16 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Connecticut

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

A nature lover's dream atop a 100-acre historic farm in North Stonington, away from the hustle and bustle of everyday life. This home offers a one-of-a-kind stay – spend your mornings in the fresh air helping the hosts tend to the farm animals in the tranquil setting to feel at one with nature – from feeding chickens and collecting eggs to brushing the horses and rooster calls here and there, but it's all part of the experience.

Magic in The Hamptons

Magic in The Hamptons

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

This beautiful home is set within dense woodland on the northern East Hampton Coast, just two blocks from a private beach looking out over Gardiners Bay. Inside, there are beautiful hardwood floors, a cosy fireplace for cool evenings and cathedral-like ceilings over the dining area.

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.


We selected the top 3% holiday homes in Connecticut Cottages

Explore the 16 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

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Salty kiss

Salty kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Mahogany

Mahogany

  • 6 guests

  • 3 bedrooms

Amenia, Dutchess County

The Old Silo

The Old Silo

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Connecticut, United States. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Connecticut Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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