Rent Luxury Holiday Cottages in Orange County

We selected the best homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

Fill your lungs with the scent of freshly chopped firewood as you step from the crisp Catskills mountain air into this gabled-roofed cottage. Whether you're a couple seeking stolen moments or a group of friends in search of calm, you'll find what you're looking for here.

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Wander Inn is an architect-renovated ranch in a beautiful setting. Built in the sixties, this home is made for relaxation and indulgence.

Hearthside Haven

Hearthside Haven

  • 4 guests

  • 2 bedrooms

Ulster County, Woodstock

Tucked neatly at the border of the Catskills, this chalet in Lake Hill is an idyllic home for those seeking an alpine retreat. With Cooper Lake and the Mink Hollow hiking trail nearby, it’s effortless to reconnect with nature here.

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866, is steeped in history and rural charm.


We selected the top 3% holiday homes in Orange County Cottages

Explore the 2 most perfect homes in our collection

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Most popular homes

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Bay Bliss

Bay Bliss

  • 6 guests

  • 4 bedrooms

Centerport, Huntington

The Archway

The Archway

  • 9 guests

  • 4 bedrooms

West Hurley, Hurley

The Berkshires Splendour

The Berkshires Splendour

  • 12 guests

  • 6 bedrooms

New Marlborough, Berkshire County

Hawk & Falcon

Hawk & Falcon

  • 10 guests

  • 4 bedrooms

Ulster County, Rochester

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Black Lips

Black Lips

  • 4 guests

  • 2 bedrooms

Woodstock, Ulster County

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Orange County, New York, United States. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Orange County Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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