Ulster County Chalets

We selected the 884 homes worth renting in this location

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Adults

Age 13+

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Age 1 to 12

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Home spotlights in Ulster County

Hawk & Falcon

Hawk & Falcon

  • 10 guests

  • 4 bedrooms

Ulster County, Rochester

Unplug, tune out and drop off the grid for a while. Nestled out of the way in the Rondout Valley in Upstate New York, this secluded barn house and cottage combo is perfect for anyone looking to get away from it all.

Woodland Hymnal

Woodland Hymnal

  • 4 guests

  • 2 bedrooms

Woodstock, Ulster County

This beautiful old clapboard church has been turned into a woodland retreat like no other, where deer regularly stroll among the trees. Just outside Woodstock, there are craft beer breweries, farm shops and mom and pop coffee shops a short drive away, and trails into the Catskills are all around.

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Sitting peacefully on the edge of North Twin Lakes, this stylish cottage sets the tone for a restorative retreat in Livingston. Featuring beautiful views, calm rooms and a range of personal touches, you’ll find everything you could need to disconnect and embrace the natural elements.

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Reminiscent of something from a Laura Ingalls Wilder novel, this picturesque cabin is a haven surrounded by peace and quiet and lush woodland. Although you can count on a serene stay here, you’re also just a five-minute drive from the quaint town of Old Chatham where you can find some local amenities, or a ten-minute drive from Chatham Town, which has several excellent restaurants and plenty of charming local shops.


We selected the top 3% holiday homes in Ulster County Chalets

Explore the 884 most perfect homes in our collection

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Most popular homes in Ulster County

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Great Mountain

Great Mountain

  • 8 guests

  • 3 bedrooms

Rosendale, New York

Soul Of The Willow

Soul Of The Willow

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

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Frequently asked questions

A chalet in Ulster County, New York, United States is the perfect accommodation for a cosy holiday. Find your dream one by browsing Plum Guide’s collection of homes. They 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 most charming chalets that Ulster County, New York, United States has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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