Book Family Friendly Rentals in Orange County

We selected the 12 homes worth renting in this location

Home spotlights in Orange County

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.

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.

The Autumn

The Autumn

  • 10 guests

  • 5 bedrooms

Chester, New York

Sitting peacefully at the end of a quiet road, this home makes for the perfect setting for friends and family to gather and celebrate life’s special moments. From fun-filled games of pool and ping pong to heart-warming gatherings around the table and cosy movie nights by the fire, this is the kind of setting that brings warmth and comfort to daily living.

The Foggy Falls

The Foggy Falls

  • 6 guests

  • 3 bedrooms

Fort Montgomery, Highlands

Based in a leafy spot in the peaceful village of Highland Falls, this idyllic and quintessentially American holiday home is waiting with open arms to welcome you on your holiday to the North East of the USA. Highland Falls is a cosy community on the bank of the Hudson, close to West Point and its fascinating museum, and also near lots of beautiful outdoor spots that make the state of New York so sought-after by those looking to be impressed by Mother Nature.


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

Explore the 12 most perfect homes in our collection

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Most popular homes in Orange County

Natural Calm

Natural Calm

  • 10 guests

  • 4 bedrooms

Blooming Grove, New York

A New Perspective

A New Perspective

  • 6 guests

  • 4 bedrooms

Orange County, Newburgh

Gone Fishing

Gone Fishing

  • 8 guests

  • 3 bedrooms

Sterling Forest, Warwick

Monroe Mountain Retreat

Monroe Mountain Retreat

  • 16 guests

  • 5 bedrooms

Blooming Grove, New York

Antique Pine

Antique Pine

  • 6 guests

  • 2 bedrooms

Pine Bush, Crawford

The Picket Fence

The Picket Fence

  • 16 guests

  • 8 bedrooms

Blooming Grove, New York

A Timeless Tale

A Timeless Tale

  • 6 guests

  • 3 bedrooms

Greenwood Lake, Warwick

The Old and the Light

The Old and the Light

  • 22 guests

  • 8 bedrooms

Stony Point, Rockland County

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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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