Ulster County Chalets

We selected the 904 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Ulster County

Sweetwater Hideaway

Sweetwater Hideaway

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Sweetwater Hideaway is a magnificently organic cabin nestled in the forestry Woodstock landscape. The timber vaulted ceiling, exposed wooden beams and deep chestnut finishings create a grand interior.

On the Edge of Nature

On the Edge of Nature

  • 4 guests

  • 3 bedrooms

Gardiner, New York

It’s the end of the line. Beyond this chalet, there’s nothing but Minnewaska’s protected preserveland.

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.

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home.


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

Explore the 904 most perfect homes in our collection

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Most popular homes in Ulster County

Hemlock & Cedar

Hemlock & Cedar

  • 2 guests

  • 1 bedrooms

Olive, Ulster County

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

The Dutch Farmhouse

The Dutch Farmhouse

  • 8 guests

  • 4 bedrooms

Saugerties, New York

Woodland Hymnal

Woodland Hymnal

  • 4 guests

  • 2 bedrooms

Woodstock, Ulster County

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield 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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Check upcoming rates & availability for Ulster County Chalets


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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