Rent Luxury Cottages in Connecticut

We selected the 140 homes worth renting in this location

Home spotlights in Connecticut

The Fifties Barn

The Fifties Barn

  • 8 guests

  • 4 bedrooms

East Hampton, The Hamptons

Once a 1950s potato barn, this historic home now provides rustic charm in the affluent Hamptons. Though we fell in love with the loft library, dramatic furnishings, and leafy garden, complete with a private pool and hot tub, the location is also worth mentioning.

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.

Gatsby's Mansion

Gatsby's Mansion

  • 42 guests

  • 11 bedrooms

Belle Terre, Brookhaven

Homes like this are one in a million. An eight-acre complex on the Port Jefferson coastline, guests will find virtually everything they could wish for at the address.

An Old Fashioned

An Old Fashioned

  • 8 guests

  • 4 bedrooms

Napeague, East Hampton

This lovely home is an ideal base in the Hamptons. It’s conveniently located on the edge of Napeague State Park and just a two-minute walk from Napeague Bay, with the gorgeous Amagansett Beach only seven minutes away by car.


We selected the top 3% holiday homes in Connecticut Cottages

Explore the 140 most perfect homes in our collection

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Most popular homes in Connecticut

Well & Happy

Well & Happy

  • 10 guests

  • 5 bedrooms

Southold, The Hamptons

Modern Beach Retreat

Modern Beach Retreat

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Coral Skies

Coral Skies

  • 6 guests

  • 3 bedrooms

Montauk, East Hampton

High Tea & Hedgerows

High Tea & Hedgerows

  • 8 guests

  • 4 bedrooms

Pawling, New York

Artistic Sensibility

Artistic Sensibility

  • 8 guests

  • 3 bedrooms

East Hampton North, East Hampton

Port & Starboard

Port & Starboard

  • 6 guests

  • 6 bedrooms

North Haven, Southampton

Make it Yours

Make it Yours

  • 8 guests

  • 4 bedrooms

East Hampton North, East Hampton

Number Nineteen

Number Nineteen

  • 13 guests

  • 6 bedrooms

Montauk, East Hampton

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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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