Book Luxury Vacation Rentals in Connecticut

Award-winning homes from £98

Home spotlights in Connecticut

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.

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.

Ranch in the East

Ranch in the East

  • 8 guests

  • 4 bedrooms

Amagansett, East Hampton

A former beach house, this home has been completely renovated and it shows. Families travelling with little ones will appreciate the gunite pool and vast outdoor space, while the firepit, hot tub and patio are perfect for evening drinks and dining.


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

Explore the 141 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

Rock Around The Clock

Rock Around The Clock

  • 10 guests

  • 7 bedrooms

Bridgehampton, Southampton

An Old Fashioned

An Old Fashioned

  • 8 guests

  • 4 bedrooms

Napeague, East Hampton

Meet Me In Montauk

Meet Me In Montauk

  • 6 guests

  • 4 bedrooms

Montauk, East Hampton

Like a Whisper

Like a Whisper

  • 11 guests

  • 7 bedrooms

Peconic, North Fork

Make it Yours

Make it Yours

  • 8 guests

  • 4 bedrooms

East Hampton North, East Hampton

The Dappled Light

The Dappled Light

  • 6 guests

  • 3 bedrooms

Springs, East Hampton

Cinematic Seascapes

Cinematic Seascapes

  • 14 guests

  • 6 bedrooms

Northwest Harbor, East Hampton

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Connecticut, United States. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Connecticut Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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