Dutchess County vacation rentals

We found 1,366 vacation rentals — enter your dates for availability

Discover a selection of 227 homes, 60 apartments, and other vacation rentals in Dutchess County that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a washer and dryer. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Popular Dutchess County destinations on Vrbo

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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.

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.

How to get to and around Dutchess County

If you're traveling by train, Poughkeepsie Station, Rhinecliff Station and Appalachian Trail are the main stations in the city.

Frequently asked questions

What is the best area to stay in Dutchess County when booking a vacation rental?
One of the most sought-after areas to choose a Vrbo vacation rental in Dutchess County is Beacon. Spend your trip here and explore its much-loved attractions, like Dia Beacon and Dutchess Stadium.
What is the most popular type of vacation rental accommodation in Dutchess County?
According to our data, apartments are the most sought-after type of vacation rental in Dutchess County. But as you might expect, everyone’s idea of an awesome stay is bound to be different. Vrbo has vacation homes in a variety of shapes and sizes, and we’ll help you find the perfect fit for you.
How much does it cost to rent a vacation rental in Dutchess County?
Season, property type and length of stay are some of the things that can determine the price of a vacation home. Simply enter your dates of travel to find your ideal fit. From comfy cabins to sprawling luxury villas, all Vrbo vacation rentals offer unbeatable value.
How much does it cost to rent a beach house in Dutchess County?
Prices for beach houses in Dutchess County vary depending on the style and size of the property and when you’re traveling. Just enter your travel dates into Vrbo and how many guests to view your options and prices. From there you can use our filter tool to tailor your search by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Dutchess County?
Good news. There are. You can choose from 67 stays that allow pets in Dutchess County on Vrbo. Our cuddly best friends also need a break, so simply use our search function for pet-friendly vacation rentals to find a perfect property where your puppy can join in the fun.
Are there large group vacation rentals in Dutchess County?
With 52 properties that can host 10 or more people in Dutchess County, you don’t have to keep anyone off the invite list. From fun family vacations to special events like birthday parties and weddings, Vrbo can help you find a large group rental to match the occasion.
What are the top attractions for families in Dutchess County?
Keep the kids busy at these leading family-friendly attractions in Dutchess County:

  • Stormville Airport Antique Show & Flea Market
  • Vanderbilt Mansion National Historic Site
  • Dia Beacon

Are there one-bedroom vacation rentals in Dutchess County?
Yes, Dutchess County has 62 one-bedroom rentals on offer. Typically located in popular spots because of their compact size, a one-bedroom property is perfect if you’re getting away with your partner or a friend. And with plenty of home comforts like full kitchens and more privacy, you’ll be able to rest and recharge while discovering this exciting destination.
Can I find two-bedroom vacation rentals in Dutchess County?
Dutchess County has 50 two-bedroom vacation properties to select from. Discover a vacation home with all the comfort and space you’re looking for at a price that’s hard to resist on Vrbo.
Are there vacation rentals with WiFi in Dutchess County?
Dutchess County has 138 vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming movies with your family to writing and sending emails, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in Dutchess County?
You’ll have your pick of 229 vacation homes with air conditioning in Dutchess County giving you that cooling breeze and extra element of comfort. Simply enter your travel dates and then take advantage of our filter tool to find stays with air conditioning.
How old do you have to be to rent a vacation rental in Dutchess County?
The minimum age permitted can differ between properties on Vrbo, so double-check the rules of the vacation rental in Dutchess County you want to book. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Dutchess County for?
The length of time you can rent a vacation rental in Dutchess County differs according to the property. Simply enter your desired dates to see a list of options offering extended stays. With lots of features like air conditioning and laundries, as well as some offering weekly or monthly discounted prices, you’re sure to discover somewhere perfect to call your home away from home in Dutchess County.
Does Vrbo offer discounts for vacation homes in Dutchess County?
On Vrbo, we’ve got some incredible discounts and deals for Dutchess County. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re planning a weekend retreat or an extended escape, Vrbo has lots of options for all styles and budgets.

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