Book Luxury Holiday Rentals in Ulster County

Award-winning homes from £98

Home spotlights in Ulster County

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods.

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

This home's architecture, interiors and colourful prints all share a mid-century modern style, but its woodland surroundings are more Hansel and Gretel than Gilbert and George. In a tiny hamlet in upstate New York, it’s surrounded by mountains, lakes and forest – great for skiers, hikers and wild swimmers alike.

Black Lips

Black Lips

  • 4 guests

  • 2 bedrooms

Woodstock, Ulster County

Whether you’re seeking contemplation in a New-Age spa or the calm of fly fishing, contemporary galleries or antiquing, the Catskill Mountains – a two hour drive from Manhattan – will gently impose its slower pace on anyone who visits. Adjacent to Woodstock’s Comeau property, a land conservancy of 76 acres of meadows, woods, playing fields and swimming holes, you’ll find this home perfectly poised between town and country.

Unscripted Upstate

Unscripted Upstate

  • 6 guests

  • 3 bedrooms

Woodstock, Ulster County

It's guaranteed love from the moment you pull up to this beautiful home in Woodstock. Step through the front door and it's like you've stumbled upon the front cover of a magazine, dramatic wooden stairs juxtaposed with chic upholstery and a light ambience.


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

Explore the 30 most perfect homes in our collection

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Most popular homes in Ulster County

Sweet Cicely

Sweet Cicely

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

Drifting On By

Drifting On By

  • 6 guests

  • 3 bedrooms

Malden-on-Hudson, Malden

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

The Ashokan

The Ashokan

  • 4 guests

  • 2 bedrooms

Glenford, West Hurley

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, Ulster County

Which Way The River

Which Way The River

  • 11 guests

  • 4 bedrooms

Shandaken, New York

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Ulster 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 Ulster 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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