Hudson Valley Guest Houses

We selected the 55 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 Hudson Valley

A Little Love Note

A Little Love Note

  • 6 guests

  • 2 bedrooms

New Lebanon, New York

Surrounded by acres of forest, flowing streams, waterfalls and historic ruins, this little cottage welcomes you to experience the natural beauty of the Berkshire mountains. Located within a former Shaker settlement, there’s an abundance of charm and character here.

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.

Which Way The River

Which Way The River

  • 11 guests

  • 4 bedrooms

Shandaken, New York

Have you ever wanted your very own slice of the Catskills? Of course, you have.

Tudoresque

Tudoresque

  • 10 guests

  • 5 bedrooms

Ossining, Westchester County

In the town of Ossining on the banks of the Hudson River, this home is reminiscent of an English Tudor mansion on the outside. Inside, there’s plenty of social space for the group to spread out – playing a game of pool in the main living room, settling in to watch Netflix by the fire, in the dedicated media room upstairs or perhaps sipping an old fashioned at the wet bar in the “sky lounge” at the top of the house.


We selected the top 3% holiday homes in Hudson Valley Guest Houses

Explore the 55 most perfect homes in our collection

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Most popular homes in Hudson Valley

Bay Bliss

Bay Bliss

  • 6 guests

  • 4 bedrooms

Centerport, Huntington

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Hemlock & Cedar

Hemlock & Cedar

  • 2 guests

  • 1 bedrooms

Olive, Ulster County

Aquarian Exposition

Aquarian Exposition

  • 14 guests

  • 6 bedrooms

Zena, Woodstock

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

Hearthside Haven

Hearthside Haven

  • 4 guests

  • 2 bedrooms

Ulster County, Woodstock

Sweet Cicely

Sweet Cicely

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

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Check upcoming rates & availability for Hudson Valley Guest Houses


Frequently asked questions

Looking for guesthouse style accommodation in Hudson Valley? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in the best guesthouse style accommodation that Hudson Valley has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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