Book Family Friendly Rentals in Ulster County

We selected the 786 homes worth renting in this location

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Home spotlights in Ulster County

Reynard's Den

Reynard's Den

  • 4 guests

  • 2 bedrooms

Liberty, New York

Escape to the Western Catskills for a break surrounded by the rustling of leaves and the calls of birds. This architecturally significant A-frame cabin sits on a secluded plot among the tall trees – a clearing just for you.

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.

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.

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 786 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

Hello Yellow Brick Road

Hello Yellow Brick Road

  • 6 guests

  • 3 bedrooms

Wawarsing, New York

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Hearthside Haven

Hearthside Haven

  • 4 guests

  • 2 bedrooms

Ulster County, Woodstock

Woodland Hymnal

Woodland Hymnal

  • 4 guests

  • 2 bedrooms

Woodstock, Ulster County

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

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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