Discover a selection of 1,000 vacation rentals in Poughkeepsie, NY 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 WiFi. Prices start at $59 per night, and houses and cabins are popular options for a stay in Poughkeepsie. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Poughkeepsie
Destination guide

Poughkeepsie shows a pretty side of New York State

Pretty little Poughkeepsie clings to the banks of the Hudson River just far enough away from the sprawl of the Big Apple to keep it sheltered from the hectic city life. A fine balance of lived-in charm and local history make it an intriguing place to while away a vacation, flitting between the local cafés, grand mansions bearing the name of Vanderbilt, presidential libraries, and the arched industrial bridges of decades gone by. What’s more, there are Poughkeepsie vacation rentals of all sorts, from hearty wood cabins to sprawling lodges for the whole family.

Things to do

Bridges and big houses in Poughkeepsie

Look for Poughkeepsie vacation rentals close to the meanders of the Hudson River if you want front-row seats over perhaps the town's most iconic landmark: The Walkway Over the Hudson. This is a reconstruction of an old 19th-century railroad, and now one of the best ways to survey New York's great river. Historic homes like the Italianate Locust Grove and Vanderbilt Mansion are great for getting a feel for the VIPs that once resided here, while the Mid-Hudson Children's Museum is perfect for keeping the little ones entertained.


Enjoyment on the edge of the Hudson River in Poughkeepsie

As Poughkeepsie meets the waters of the Hudson River, it invites travelers to stroll the tree groves and green parks that line its banks. Crossing the river is a must, what with the longest footbridge in the world arching its steel girders over to the far side from Downtown. Then comes the array of regal manor houses, historic sites, and golf clubs that pepper the surrounding countryside, not to mention the lively comedy clubs and entertainment venues that fringe Main Street and Market, all channeling the boho vibes of New York.


Summertime on the Hudson, Poughkeepsie style

With its bridge walks and leafy riverside parks, there's no question that Poughkeepsie is best seen in the spring or summertime. Search for those Poughkeepsie vacation rentals any time after May and before the onset of the fall in October to ensure you get warm, long, and mostly dry days to hop between the heritage homes and the al fresco café-bars along the waterside here. Fall can also be beautiful though, especially if you're eager to see the changing of the colors in the New York forests in November.

Natural features

Poughkeepsie sits nestled on the Hudson

Poughkeepsie’s location gives it great access to the maple and oak forests that line the edge of the river, which are often at their best in the nearby state parks – the Franny Reese State Park and the Illinois Mountain Park. Spots like that mean walking trails, wetland habitats, bicycle routes, and chances to see wild buck deer, not to mention some marked cross-country skiing tracks in the winter.

How to get there

Transportation to and around Poughkeepsie

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 16.3 mi (26.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 32.3 mi (52 km) away.

If you're traveling by train, the main station serving the city is Poughkeepsie Station.

How many vacation rentals are available around Poughkeepsie, NY?

Our 2021 property listings offer a large selection of 848 vacation rentals around Poughkeepsie. From 614 house rentals to 104 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Poughkeepsie?

Vrbo offers a large selection of vacation rentals near lovely places in Poughkeepsie. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Bardavon 1869 Opera House: 358 vacation rentals
  • Marist College: 362 vacation rentals
  • Vassar College: 342 vacation rentals
  • Mid-Hudson Bridge: 362 vacation rentals
  • Poughkeepsie Station: 363 vacation rentals

But there are many other points of interest around Poughkeepsie listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Poughkeepsie?

Yes, of course. Vrbo has 614 Houses in Poughkeepsie. Our other popular types of vacation rentals in Poughkeepsie include:

  • Cabins: 104 rentals available
  • Condos/Apartments: 72 rentals available
  • Cottages: 98 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Poughkeepsie?

Yes, you can select your preferred vacation rental with pool among our 186 vacation rentals with pool available in Poughkeepsie. Please use our search bar to access the selection of vacation rentals available.