Ulster County Holiday Homes with Staff

We selected the 884 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

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Home spotlights in Ulster County

Upstate Escape

Upstate Escape

  • 10 guests

  • 4 bedrooms

Woodstock, Ulster County

Tucked away just outside of Woodstock, this impressive home welcomes families and friends to spend a few relaxing days in the Hudson Valley. Fully renovated in 2017, your hosts have truly thought of everything to ensure anyone who stays here has a magical experience.

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.

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Once an 1890s carriage house, this home has been designed for country living for a small family. Low timber ceilings and hardwood floors retain the barn-like element, but instead of hay bales, you’ve got comfortable king-size beds for grown-ups and secret sleeping spots for kids in the mezzanine above the loft.

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Built in 1800, Hitchbrook is a quintessential New England home. Surrounded by farmland and rolling hills, this home is a private getaway for those looking for a pastoral retreat.


We selected the top 3% holiday homes in Ulster County Holiday Homes with Staff

Explore the 884 most perfect homes in our collection

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Most popular homes in Ulster County

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Great Mountain

Great Mountain

  • 8 guests

  • 3 bedrooms

Rosendale, New York

Sweetwater Hideaway

Sweetwater Hideaway

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

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Check upcoming rates & availability for Ulster County Holiday Homes with Staff


Frequently asked questions

Are you hoping for a stay in one of the best holiday homes with staff in Ulster County, New York, United States? If so, you've definitely come to the right place. Reach out to our expert team who will happily arrange for staff to be present at your home in Ulster County, New York, United States as an addition to your booking. Our Plum Guide homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short extended stay. Should you need anything, our friendly team is on hand 24/7, so just ask.

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