Book Family Friendly Rentals in Orange County

We selected the 6 homes worth renting in this location

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Home spotlights

Gone Fishing

Gone Fishing

  • 8 guests

  • 3 bedrooms

Sterling Forest, Warwick

Gone Fishing has all the comfort and convenience of city living, but right in the middle of the woods. Serve up hearty meals for the group out on the terrace, or cosy up by the fireplace in winter and watch the snow falling on the trees.

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

It's back to camp at this lakeside home, which has been designed to make the most of its beautiful surroundings. Wooden floorboards, adjoining cabins, folding doors, and outdoor walkways give the sense of being in a giant – and rather quirky – treehouse.

A New Perspective

A New Perspective

  • 6 guests

  • 4 bedrooms

Orange County, Newburgh

On the bank of the Hudson river lies A New Pespective. Designed by renowned architect Philip Johnson in the late 20th Century, attention has been paid to every element of the architecture here.

Hudson Grandeur

Hudson Grandeur

  • 16 guests

  • 8 bedrooms

Cornwall, Orange County

This grand, old home in the Hudson Valley feels like a mix between a beautiful Midwest farmhouse and an English manor. A blue clapboard facade and white bannisters suggest country-chic while the pristine white columns at the entrance add the grandeur.


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

Explore the 6 most perfect homes in our collection

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Most popular homes

A Timeless Tale

A Timeless Tale

  • 6 guests

  • 3 bedrooms

Greenwood Lake, Warwick

Antique Pine

Antique Pine

  • 6 guests

  • 2 bedrooms

Pine Bush, Crawford

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

Dahlia Darling

Dahlia Darling

  • 10 guests

  • 5 bedrooms

Bethel, New York

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

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Check upcoming rates & availability for Orange County Family Friendly Rentals


Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Orange 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 Orange 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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