Book Luxury Holiday Rentals in Columbia County

Award-winning homes from £98

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Home spotlights in Columbia County

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court.

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Mere steps from the beach, this four-bedroom farmhouse sleeps ten and is ideal for a large family getaway. Rustic it may be, but the interiors don’t skimp on style – white walls and pops of colour lend it a modern Scandinavian vibe.

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, Ulster County

This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home.

A Little Love Note

A Little Love Note

  • 6 guests

  • 2 bedrooms

New Lebanon, New York

Surrounded by acres of forest, flowing streams, waterfalls and historic ruins, this little cottage welcomes you to experience the natural beauty of the Berkshire mountains. Located within a former Shaker settlement, there’s an abundance of charm and character here.


We selected the top 3% holiday homes in Columbia County Holiday Rentals

Explore the 922 most perfect homes in our collection

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Most popular homes in Columbia County

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

The Mountain Glow

The Mountain Glow

  • 6 guests

  • 3 bedrooms

Callicoon, New York

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Hanging Baskets

Hanging Baskets

  • 3 guests

  • 2 bedrooms

Hudson, Columbia County

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Columbia County. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Columbia County has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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