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.
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.
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.
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.
If you're traveling by train, Poughkeepsie Station, Rhinecliff Station and Appalachian Trail are the main stations in the city.
From high-end condos to intimate cottages, Vrbo has properties to suit every taste and budget. Here are some of the top vacation rentals in Dutchess County:
For even more great options, use the search bar at the top of the page to find the perfect Dutchess County vacation rental for you.
Punching far above its weight when it comes to character and charm, a tiny house vacation rental in Dutchess County delivers big adventure. Shut off your gadgets and switch your focus to Mother Nature at one of these fun-sized escapes:
Whether you're after a rustic retreat or a luxurious escape, we've got some great log cabins to rent in Dutchess County. Experience a blend of comfort and adventure at one of these options:
Whether you're planning a quick family trip, a romantic rendezvous or a couple of nights away by yourself, we've got weekend getaways in Dutchess County to suit your needs. Pack some clothes into an overnight bag and stay at one of these much-loved properties:
Ditch the run-of-the-mill hotel room and secure one of our studio apartments in Dutchess County. Here's where you can hunker down in your own digs and experience your next destination like a local:
Book yourself an inexpensive cabin or ignore your accountant and live it up a little in a luxury condo. Vrbo has lots of short-term rentals for your vacation in Dutchess County. Take a look at these properties for inspiration:
Whether you've been together for a month, a year or an eternity, there's nothing like a romantic weekend getaway to fan the flames of love. If you're after the perfect place to spend a few days with your honey, you'll be wooed by these retreats:
When it comes to planning a vacation, we believe the more the merrier. If you're in search of a getaway with enough space to fit the whole family, one of these large group vacation rentals in Dutchess County might be just the ticket:
There are plenty of houses with a pool in Dutchess County, so don your swimsuit and get ready to spend your days chilling by the water. Here are two top options to get you inspired:
We've got large family vacation rentals that'll fit the whole darn tree — yes, even those long-lost cousins of yours! Whatever type of property you want, you'll find the best option on Vrbo. Here are a few of our favorites in Dutchess County:
If you're chasing family-friendly attractions in Dutchess County, you're spoiled for choice. SplashDown Beach, Dutchess County Fairgrounds and Poughkeepsie Bridge promise crowd-pleasing fun for young and old.