Book Family Friendly Rentals in Ulster County

We selected the 788 homes worth renting in this location

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Home spotlights in Ulster County

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866, is steeped in history and rural charm.

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, Ulster County

This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home.

Highwoods Retreat

Highwoods Retreat

  • 12 guests

  • 5 bedrooms

Saugerties, New York

This secluded home is set on 26 acres of private land. You may be in rural Saugerties, but with a private pool, seven-seater cinema, and shuffleboard table, there’s plenty to keep you occupied here.


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

Explore the 788 most perfect homes in our collection

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Most popular homes in Ulster County

The Willow's Resting Place

The Willow's Resting Place

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Hearthside Haven

Hearthside Haven

  • 4 guests

  • 2 bedrooms

Ulster County, Woodstock

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

Sweet Cicely

Sweet Cicely

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Antique Pine

Antique Pine

  • 6 guests

  • 2 bedrooms

Pine Bush, Crawford

Upstate Escape

Upstate Escape

  • 10 guests

  • 4 bedrooms

Woodstock, Ulster County

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Ulster County, New York, United States. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Ulster County Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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