Book Luxury Short Stay Rentals in Orange County

We selected the 14 homes worth renting in this location

Home spotlights in Orange County

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.

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.


We selected the top 3% holiday homes in Orange County Short Stay Rentals

Explore the 14 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

White Pine Hideout

White Pine Hideout

  • 6 guests

  • 3 bedrooms

Blooming Grove, New York

Willow Tree View

Willow Tree View

  • 8 guests

  • 4 bedrooms

Blooming Grove, New York

The Picket Fence

The Picket Fence

  • 16 guests

  • 8 bedrooms

Blooming Grove, New York

Antique Pine

Antique Pine

  • 6 guests

  • 2 bedrooms

Pine Bush, Crawford

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in Orange County, New York, United States. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Orange County luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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