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.

Where to stay around Poughkeepsie?

Our 2019 property listings offer a large selection of 784 vacation rentals near Poughkeepsie. From 488 Houses to 99 Cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Poughkeepsie for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Poughkeepsie?

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

  • Bardavon 1869 Opera House: 334 vacation rentals
  • Marist College: 339 vacation rentals
  • Mid-Hudson Bridge: 340 vacation rentals
  • Poughkeepsie Station: 339 vacation rentals
  • Overlook Drive-In Theater: 325 vacation rentals

But there are many other points of interest around Poughkeepsie listed on HomeAway 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. HomeAway has 488 Houses in Poughkeepsie. Our other popular types of vacation rentals in Poughkeepsie include:

  • Cabins: 99 rentals available
  • Cottages: 99 rentals available
  • Farmhouses: 40 rentals available

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

Can I find a vacation rental with pool in Poughkeepsie?

Yes, you can select your preferred vacation rental with pool among our 214 vacation rentals with pool available in Poughkeepsie. Please use our search bar to access the selection of vacation rentals available.

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