Columbia County Ski Resort Rentals

We selected the best homes worth renting in this location

Home spotlights in Columbia County

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.

Hudson Hideaway

Hudson Hideaway

  • 8 guests

  • 5 bedrooms

Columbia County, Stuyvesant

This beautiful home stands on 14 acres in the countryside of Stuyvesant, with a backdrop of the Catskill Mountains. The restored barn makes for a stunning base for getaways with family and friends, with heaps of space.

Whispering Red Pines

Whispering Red Pines

  • 8 guests

  • 4 bedrooms

Milan, New York

This rustic red A-Frame sits in the hamlet of Milan and offers a rural retreat in the heart of the Hudson Valley, just two hours from bustling NYC. With over six acres of land, you’ll feel totally remote here, though Red Hook, Rhinebeck and Tivoli are within easy driving distance should you feel like a day exploring the music stores, coffee shops and vintage diners.

Pondering Soul

Pondering Soul

  • 14 guests

  • 7 bedrooms

Copake, New York

Designed by a renowned architect, and tastefully furnished, this award-winning home is built for coming together for quality time spent as a group, while still allowing guests ample privacy. Enjoy blissful peace and serenity amidst the 45 private acres of rolling hills and large ponds that surround the property.


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

Explore the 4 most perfect homes in our collection

View on map

Most popular homes in Columbia County

View all


Frequently asked questions

Explore our collection of ski resort rentals in Columbia County, New York, United States. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the best ski resort rentals that Columbia County, New York, United States has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

Search Our Collection