Rent Luxury Holiday Cottages in Connecticut

We selected the 62 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

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Originally built in the 1800s as a fisherman’s shanty, this traditional cedar-shingled building has since been restored into a peaceful waterside sanctuary – it's the perfect setting to relax, reflect and listen to the soothing sound of the sea. Inside, the owners have honoured the integrity of the space whilst integrating a range of vintage and handcrafted furnishings – each with its own story and tale from travels near and far.

Lost In The Mountains

Lost In The Mountains

  • 10 guests

  • 3 bedrooms

Pocono Pines, Tobyhanna Township

A waterfront home in the Pocono Pines – yes please. Huge windows make it feel like you’re in the middle of the forest, though you’ll be able to pay for access to a premium club nearby, where you can golf, swim and play tennis – you get the peace of the wilderness with the amenities of a resort.

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

This delightful cottage, nestled in the picturesque mountains of New York State’s famous Shawangunk Ridge, is an ideal spot for a cosy country escape. As the last property before the entrance to a protected nature reserve, this home offers unmatched tranquillity and proximity to nature.

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.


We selected the top 3% holiday homes in Connecticut Cottages

Explore the 62 most perfect homes in our collection

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Most popular homes in Connecticut

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

The Mountain Glow

The Mountain Glow

  • 6 guests

  • 3 bedrooms

Callicoon, New York

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

Hawk & Falcon

Hawk & Falcon

  • 10 guests

  • 4 bedrooms

Ulster County, Rochester

Blissful Thinking

Blissful Thinking

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Walcott

Walcott

  • 8 guests

  • 3 bedrooms

Bridgehampton, Southampton

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Connecticut. 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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