Dutchess County, NY, USA

Dutchess County, NY, USA

We found 192 vacation rentals — enter your dates for availability


Find the best place to stay — Dutchess County

Where to stay near Dutchess County, US?

Our 2018 property listings offer a large selection of 192 vacation rentals near Dutchess County. From 112 houses to 0 , 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 HomeAway.

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.