Where to stay around Dutchess County, US?

Our 2018 property listings offer a large selection of 179 vacation rentals near Dutchess County. From 102 Houses to 21 Cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Dutchess County for a holiday or a weekend are on VRBO.

What are the most popular destinations to visit in Dutchess County?

There are many lovely places to stay for a holiday trip or just for a weekend in Dutchess County. From VRBO travelers, the top most popular destinations to visit are:

  • Town of Stanford: 157 vacation rentals
  • Town of Union Vale: 70 vacation rentals
  • Millbrook Vineyards and Winery: 299 vacation rentals
  • Clermont State Historic Site: 894 vacation rentals
  • Millbrook: 497 vacation rentals

And VRBO offers you the chance to discover many other popular destinations in Dutchess County! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Dutchess County?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Dutchess County:

  • Millbrook: 497 rentals
  • Millerton: 208 rentals
  • Rhinebeck: 564 rentals
  • Fishkill: 226 rentals
  • Poughkeepsie: 592 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to Dutchess County?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Dutchess County are:

  • Poughkeepsie, NY (POU-Dutchess County): 269 vacation rentals
  • Stormville Airport (N69): 224 vacation rentals
  • Hudson, NY (HCC-Columbia County): 504 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Dutchess County?

VRBO offers a large selection of rentals near lovely places in Dutchess County. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Millbrook Vineyards and Winery: 299 rentals
  • Clermont State Historic Site: 894 rentals
  • Fishkill Golf Course: 196 rentals
  • Fishkill Ridge: 202 rentals
  • Poughkeepsie Station: 325 rentals

But there are many other points of interest around Dutchess County listed on VRBO where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Farm-to-table eating in upstate New York

Dutchess County sits north of New York City, with the mighty waters of the Hudson River to the west and backing onto Connecticut to the east. Here, you can stay in one of the many Dutchess County vacation rentals and explore the rich history, lush scenery, and fine cuisine of the region. The Hudson River Valley in upstate New York has plenty of outdoor activities on offer, including horseback riding, hiking, mountain biking, golf, and kayaking. Agricultural is thriving here, and you can't travel far without coming across a farm creating artisanal cheeses, breads, and other local delicacies.

Cross the Appalachian Scenic Trail

The Hudson River Valley landscape lends itself to weekenders from the city or vacationers who come to mountain bike, walk along the trails, or ride horses through the meadows. If you're a hiker, you can walk along part of the Appalachian Scenic Trail which passes through Dutchess County. This legendary landscape is perhaps best seen from up above, though, and several hot air balloon companies offer you the opportunity to look down over the river, forests, and meadows. Between December and February, the snows also bring in a whole host of winter activities for you to enjoy.

Visit the Scottish-style castle

The county's proximity to New York City means there is no shortage of historical sites to visit. The Montgomery Place Campus at Bard College sits within a well-manicured 380-acre estate of rolling gardens and is a National Historic Landmark. When you stay at one of the Dutchess County vacation rentals, you can also visit the Scottish-style Bannerman's Castle, which was built in the early 20th century. Alternatively, you can explore the Franklin D. Roosevelt Library and Museum which chronicles his presidency through the Great Depression and World War 2, before stopping to taste the wares at a local vineyard.

New York vacations all year round

Roughly half the days of the year in Dutchess County are sunny, though the climate can be a touch fickle with rains through the spring, summer, and fall. During the warm summer, you can settle into a Dutchess County vacation rental and look forward to hiking along the Hudson River or looking down over the landscape of forests and vineyards from an aerial tour. During the winter, it can get pretty snowy around these parts, but that just opens up opportunities for snowshoeing, ice skating, and cross-country skiing.

A bird lover's haven

The Hudson River Valley is a landscape of meadows and forests punctuated by small farms which rear cattle and grow local produce. Many vineyards have popped up in recent years and have changed the landscape somewhat with rows of vines. Birders will find plenty of animals to train their binoculars on, while snows blanket the upstate valley during December and January, creating a winter wonderland of glistening ice that hangs from the trees. This can be one of the best times to stay in a Dutchess County vacation rental.