Dutchess County Vacation Rentals, New York: house rentals & more

Discover a selection of 235 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

Poughkeepsie which includes fall colors and a river or creek

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The Farm at Hyde Park

Sleeps 5 · 2 bedrooms · 1 bathroom

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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?

Among the more in-demand destinations to choose a vacation property in Dutchess County is Rhinebeck. Base yourself here and discover some must-see attractions, including Dutchess County Fairgrounds and Old Rhinebeck Aerodrome.

What is the most popular type of vacation rental accommodation in Dutchess County?

Based on our research, houses are the most in-demand property type in Dutchess County. But as you might expect, everyone's idea of the perfect stay differs. Vrbo has vacation rentals of all sizes, shapes and budgets, and we'll help you locate the perfect fit for you.

How much does it cost to rent a vacation rental in Dutchess County?

A number of factors affect the price of a vacation rental in Dutchess County, including the type of property, season and length of stay. Still, all Vrbo homes have something in common — amazing value. Simply add your travel dates to find your dream escape.

How much does it cost to rent a beach house in Dutchess County?

When you travel and the style and size of the property will influence the cost of your beachside stay. Click on your Dutchess County travel dates to see your options on Vrbo. Did someone just say "private pool"? Use the filters to choose the features and amenities you need.

What are popular rental amenities in Dutchess County?

A stovetop, off-street parking options and a fridge head the list of most popular rental amenities in Dutchess County. Whether you're taking a trip on your own, with your other half or a group of family members, Vrbo can help you find a vacation home that fits your tastes with all the conveniences you're looking for.

Are there large group vacation rentals in Dutchess County?

Choose from 44 properties in Dutchess County that can host a group of 10 or more people. Whether you're planning a trip with extended family or a special event, there's plenty of room to get your favorite people together under one roof.

What are the top attractions for families in Dutchess County?

Keeping the kids happy during your stay in Dutchess County is a snap with these leading family-friendly attractions:

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

Can I find two-bedroom vacation rentals in Dutchess County?

Dutchess County has 44 two-bedroom vacation rentals to choose from. Enjoy a vacation home with all the space and privacy you want at a price that's hard to resist on Vrbo.

Are there vacation rentals with WiFi in Dutchess County?

Dutchess County has 108 vacation rentals with WiFi, so you'll be able to stay connected while you're away. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to checking emails, these Vrbo homes make it a breeze to go online.

How old do you have to be to rent a vacation rental in Dutchess County?

The age limit can differ across properties on Vrbo, so be sure to check the rules of the vacation rental in Dutchess County you're considering. But typically, it's 16, 18 or 21.

How long can I rent a vacation rental in Dutchess County for?

It's up to the Dutchess County property. To view all available options offering extended stays, just type your dates and number of guests into Vrbo. You can enjoy having the place to yourself, along with home comforts like air conditioning, a kitchen and a backyard where your little ones can play. Keep your eyes open for any long-term stays that offer weekly or monthly discounts.