Discover a selection of 500 vacation rentals in Dutchess County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $84 per night, and houses and cabins are popular options for a stay in Dutchess County. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Dutchess County
Destination guide

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.

Things to do

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.


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.


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.

Natural features

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.

How many vacation rentals are available around Dutchess County, US?

Our 2021 property listings offer a large selection of 747 vacation rentals around Dutchess County. From 574 house rentals to 70 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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:

  • Rhinebeck: 686 vacation rentals
  • Beacon: 201 vacation rentals
  • Poughkeepsie: 835 vacation rentals
  • Rhinebeck Village: 184 vacation rentals
  • Red Hook: 553 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:

  • Rhinebeck: 686 rentals
  • Beacon: 201 rentals
  • Poughkeepsie: 835 rentals
  • Red Hook: 553 rentals
  • Pawling: 131 rentals

For other cities, 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:

  • Eleanor Roosevelt National Historic Site: 364 rentals
  • Bardavon 1869 Opera House: 354 rentals
  • Omega Institute: 586 rentals
  • Old Rhinebeck Aerodrome: 707 rentals
  • Franklin D. Roosevelt Presidential Library and Museum: 397 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.

Explore destinations around Dutchess County

686 vacation rentals
201 vacation rentals
835 vacation rentals
Red Hook
553 vacation rentals
131 vacation rentals
307 vacation rentals
668 vacation rentals
Hyde Park
336 vacation rentals
Wappingers Falls
58 vacation rentals
Clinton Corners
181 vacation rentals
222 vacation rentals
581 vacation rentals
Hopewell Junction
118 vacation rentals
172 vacation rentals
Pine Plains
565 vacation rentals
121 vacation rentals
58 vacation rentals
70 vacation rentals
Dover Plains
93 vacation rentals
168 vacation rentals