Orange County Weekend House Rentals

We selected the 14 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.

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.

Natural Calm

Natural Calm

  • 10 guests

  • 4 bedrooms

Blooming Grove, New York

For those in search of a rustic retreat filled with the warmth and charm of country living, this cabin-inspired home welcomes you to put down your bags, and experience its range of comforting features. From lazy afternoons by the fire to long soaks in the jacuzzi bath and magical evenings gathered around the table, every detail of this setting inspires a wonderful sense of relaxation.

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.


We selected the top 3% holiday homes in Orange County Weekend House Rentals

Explore the 14 most perfect homes in our collection

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Most popular homes in Orange County

A New Perspective

A New Perspective

  • 6 guests

  • 4 bedrooms

Orange County, Newburgh

Gone Fishing

Gone Fishing

  • 8 guests

  • 3 bedrooms

Sterling Forest, Warwick

The Autumn

The Autumn

  • 10 guests

  • 5 bedrooms

Chester, New York

White Pine Hideout

White Pine Hideout

  • 6 guests

  • 3 bedrooms

Blooming Grove, New York

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

Willow Tree View

Willow Tree View

  • 8 guests

  • 4 bedrooms

Blooming Grove, New York

A Timeless Tale

A Timeless Tale

  • 6 guests

  • 3 bedrooms

Greenwood Lake, Warwick

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Frequently asked questions

Looking to book a holiday rental for the weekend in Orange County, New York, United States? You've come to the right place: we’re the official selection of the world’s best homes. Our collection of weekend rentals in Orange County, New York, United States come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. We obsessively check each home for you, so you can book with peace of mind. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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