Luxury Long Stay Rentals in Dutchess County

We selected the 902 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 in Dutchess County

High Tea & Hedgerows

High Tea & Hedgerows

  • 8 guests

  • 4 bedrooms

Pawling, New York

This home sits pretty as an English manor in the countryside of upstate New York, a ten-minute drive from the picturesque town of Pawling. Grecian-style columns greet you on arrival and the striking white facade glows against the verdant green gardens – it sits on 18 acres of land.

The Great Harvest

The Great Harvest

  • 34 guests

  • 10 bedrooms

Coolbaugh Township, Monroe County

Tucked away near Tobyhanna State Park and with valleys, mountains and forests all a short drive away, this home is perfectly situated for the adventurous. While it has a rather basic interior, we think with a full roster of guests, you may not notice.

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home.

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Just steps away from a private community beach, Borne Back was designed by its architect owner to provide a comfortable contemporary home in a perfectly quiet spot in the Hamptons. On a full acre plot next to Gardiner's Bay, it's surrounded by tall trees.


We selected the top 3% holiday homes in Dutchess County Long Stay Rentals

Explore the 902 most perfect homes in our collection

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Most popular homes in Dutchess County

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Rise with the Sun

Rise with the Sun

  • 20 guests

  • 8 bedrooms

Pleasant Valley, New York

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

On the Edge of Nature

On the Edge of Nature

  • 4 guests

  • 3 bedrooms

Gardiner, New York

Reynard's Den

Reynard's Den

  • 4 guests

  • 2 bedrooms

Liberty, New York

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Check upcoming rates & availability for Dutchess County Long Stay Rentals


Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Dutchess County. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Dutchess County collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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