Book Family Friendly Rentals in Ulster County

We selected the 790 homes worth renting in this location

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Home spotlights in Ulster County

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.

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.

Which Way The River

Which Way The River

  • 11 guests

  • 4 bedrooms

Shandaken, New York

Have you ever wanted your very own slice of the Catskills? Of course, you have.

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.


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

Explore the 790 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

Hawk & Falcon

Hawk & Falcon

  • 10 guests

  • 4 bedrooms

Ulster County, Rochester

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

On the Edge of Nature

On the Edge of Nature

  • 4 guests

  • 3 bedrooms

Gardiner, New York

Sweet Cicely

Sweet Cicely

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Antique Pine

Antique Pine

  • 6 guests

  • 2 bedrooms

Pine Bush, Crawford

Hello Yellow Brick Road

Hello Yellow Brick Road

  • 6 guests

  • 3 bedrooms

Wawarsing, New York

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Check upcoming rates & availability for Ulster County Family Friendly Rentals


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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