Book Luxury Holiday Rentals in Columbia County

Award-winning homes from £98

Home spotlights in Columbia County

Hudson Haven

Hudson Haven

  • 6 guests

  • 3 bedrooms

Gallatin, Columbia County

Nestled on three private acres, this home offers a tranquil escape from everyday life. Surrounded by woodland and meadows, complete with walking trails and a stream-fed pond, there’s so much to explore here – just watch the little ones and your four-legged friends around the pond, as it’s not fenced.

Sunset on the Porch

Sunset on the Porch

  • 4 guests

  • 2 bedrooms

Greenport, Columbia County

This charming home is the perfect place to escape the hustle and bustle of city life. It’s in the heart of Hudson Valley, close to the Berkshires and the Catskills.

Serenity Escape

Serenity Escape

  • 6 guests

  • 3 bedrooms

Taghkanic, New York

To be honest, we were totally captivated by the panoramic vistas of the Hudson Valley at this home. They are best enjoyed from the heated pool or, for another spectacle, sit by the fire pit and witness the starry sky.

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 16 most perfect homes in our collection

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Most popular homes in Columbia County

Quaint Haven

Quaint Haven

  • 2 guests

  • 1 bedrooms

Hudson, Columbia County

Enchanted Schoolhouse Retreat

Enchanted Schoolhouse Retreat

  • 6 guests

  • 3 bedrooms

Stockport, New York

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

Jewel on the Hudson

Jewel on the Hudson

  • 10 guests

  • 5 bedrooms

Coxsackie, New York

Whispering Red Pines

Whispering Red Pines

  • 8 guests

  • 4 bedrooms

Milan, New York

Hudson Valley Hideaway

Hudson Valley Hideaway

  • 6 guests

  • 3 bedrooms

Stockport, New York

Hudson Hideaway

Hudson Hideaway

  • 8 guests

  • 5 bedrooms

Columbia County, Stuyvesant

Venus In Furs

Venus In Furs

  • 6 guests

  • 3 bedrooms

Hudson, Columbia County

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Columbia County, New York, United States. 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, New York, United States 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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