Discover a selection of 71 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 $90 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.


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 to get there

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.

What are the top vacation rentals in Dutchess County?

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:

  • "Log Cabin On A Lake With Private Dock One Hour From Nyc": This Hudson Valley rental offers 3 bedrooms and is highly rated among visitors. Conveniences such as a nearby hospital and a stovetop will help you feel right at home.
  • "Welcome To The Country - Lake Front Property": Stay at this option in Red Hook and take advantage of towels, a free nearby fitness center and more. It has 1 bedroom to accommodate the ones you love.

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.

What are the best tiny house vacation rentals in Dutchess County?

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:

  • Leave the everyday behind and disappear to "Breezy Hill Tiny House - Rustic And Cozy Tiny House Getaway". This property in Accord packs plenty of conveniences into its cozy space, such as a microwave oven and a barbecue grill.
  • Alternatively, get comfy at "This Tiny House With In Door And Outdoor Fire Place Is 15 Min. From Lego Land". Located in Middletown, this little abode comes with lowered locks and a stovetop.

Can I find log cabins to rent in Dutchess County?

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:

  • If you want to be able to go fishing and golf while staying in Dutchess County, "Log Cabin On A Lake With Private Dock One Hour From Nyc" in Hudson Valley will be an excellent choice.
  • Another excellent choice is "Serene, Peaceful Get - Away - Log Cabin By The Lake". With fun activities such as kayaking and cycling nearby, this Town of Beekman retreat will be ideal if you love the outdoors.

What are the top-rated vacation rentals for weekend getaways in Dutchess County?

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:

  • "Charming Stone Chalet In Wooded Surroundings With Heated Pool Spring To Fall" - Situated in Town of Stanford, there's loads of fantastic stuff to see and do near this rental property. Handy amenities like an outdoor pool and a microwave oven will make your stay even more comfortable.
  • "Millbrook Country Dream Tennis. Swim. Play. Picnic" - This is another option with all the extras that make for a special weekend away. Make use of cable/satellite TV services and towels at this Millbrook rental property.

Can I find studio apartments for rent in Dutchess County?

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:

  • Settle in and make yourself comfortable at "Welcome To The Country - Lake Front Property", situated in Red Hook. There are loads of amenities to make use of here, including a kitchen and a boat.
  • Start the day with a cup of coffee and some freshly cooked eggs at "Studio Near Millbrook, Poughkeepsie Area W". This Pleasant Valley studio has all the conveniences you need to make your visit cozy, including an oven and a hair dryer.

Can I find short term rentals in Dutchess County?

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:

  • "Charming Stone Chalet In Wooded Surroundings With Heated Pool Spring To Fall" in Town of Stanford is a perfect place for a short-term stay. It's only a stone's throw from the town center, so you can easily see all the best sights without having to travel too far.
  • "Millbrook Country Dream Tennis. Swim. Play. Picnic" also welcomes short-term guests. Spend a couple of lazy days at this property in Millbrook and discover why it's a favorite among many visitors.

What are the best romantic weekend getaways in Dutchess County?

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:

  • Catch up on quality time and cuddles at "Log Cabin On A Lake With Private Dock One Hour From Nyc" in Hudson Valley. A fireplace and winery tours are just two of the nice touches you'll find here.
  • Another appealing option is "Welcome To The Country - Lake Front Property" in Red Hook. Enjoy perks here including a fireplace and winery tours, in addition to each other's company.

What are the best large group vacation rentals in Dutchess County?

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:

  • "Orchard Hill - Large Family Estate": With 7 bedrooms, everyone can be a part of the fun at this sought-after getaway in Millbrook. A garden and a swimming pool are just a couple of the amenities offered here.
  • "Large Renovated Historic House In Heart Of Poughkeepsie": This retreat in Poughkeepsie has 6 bedrooms, so you won't have to leave anyone off your invite list. A nearby river and a kitchen are among its many highlights.

What are the best houses for rent with a pool in Dutchess County?

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:

  • Little kids, big kids, parents — everyone will want to chill by the pool at "The Waterfall House". Treat the family to a vacation at this Town of Union Vale rental home which also comes with a living room and books.
  • Wake up and take a refreshing early morning dip at "The Beech House - Light, Open, Stunning Views" in Millbrook. A toaster and a separate dining area are just two of the many amenities available here.

What are the best large family vacation rentals in Dutchess County?

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:

  • For size, style and function, you can't go wrong with "Charming Stone Chalet In Wooded Surroundings With Heated Pool Spring To Fall". Located in Town of Stanford, this retreat offers 4 bedrooms and handy amenities like a swimming pool and a fridge. It can comfortably sleep up to 8 guests.
  • Another wonderful option is "Orchard Hill - Large Family Estate". Situated in Millbrook, this excellent escape features 7 bedrooms and lots of great amenities including childrens activities and cable/satellite TV services. It can accommodate up to 12 people.

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.

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