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33 Poughkeepsie Holiday Rentals

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Compare Poughkeepsie holiday rentals from 5 rental sites including Expedia, Booking.com, HRS Holidays and more, from $49 a night.
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Poughkeepsie Information

About Poughkeepsie

Poughkeepsie, located halfway between Albany and New York City, is nicknamed “The Queen City of the Hudson” for its Dutch heritage and proximity to the Hudson River. It was purchased from Native Americans in 1686 and retains much of its natural beauty and rich history. The name “Poughkeepsie,” pronounced “puh-KEEP-see,” derives from the Wappinger word meaning “the reed-covered lodge by the little-water place.” From the abundance of registered historic places to the variety of activities, Poughkeepsie is sure to have something for every traveler.

Things to do in Poughkeepsie

For a unique view of Poughkeepsie, simply take a stroll over the Walkway Over the Hudson. This linear park connects the Town of Lloyd to Poughkeepsie and allows visitors to see the Hudson River from above. At 212 feet tall and spanning 1.28 miles, this scenic state park is the longest elevated pedestrian bridge in the world!

Lovers of history and higher education can’t miss a visit to Vassar College. Though it is now a coeducational institution, Vassar was an exclusively women’s school for over 100 years, where it was the first institution of higher education to offer degrees to women! The campus is also an arboretum, offering manicured gardens, beautiful architecture, and the Francis Lehman Loeb Art Center.

Children and adults alike will find something entertaining at the Mid-Hudson Children’s Museum. This interactive museum offers interactive exhibits, hands-on educational programs, and special events for kids! Visit during a movie night or one of their free family nights.

Day Trips from Poughkeepsie

The Pocono Mountains, a two-hour drive from Poughkeepsie, offer activities for every type of traveler. Escape to the mountains for hiking, go rafting down the rapids, or even try mountain biking! For a more relaxed vacation, check out the many romantic bed and breakfasts or have an elegant dinner at one of the Poconos downtown areas. It is also the home of the Poconos Raceway, a famous NASCAR speedway!

Only 80 miles away, New York City offers a dizzying array of activities. To make the most of your day here, stick to centrally-located Manhattan for access to some great sightseeing. Visit Central Park, take a trip back in time at the Grand Central Terminal, and have a slice of pizza at Grimaldi’s Pizzeria under the Brooklyn Bridge.

A highland region in western Massachusetts, the Berkshires offer shopping, festivals, nature, and hundreds of cultural attractions. Visit the Norman Rockwell Museum, listen to a musical masterpiece by the Boston Symphony Orchestra, or enjoy whitewater rafting and hiking. Visit during autumn for spectacular foliage, and be sure to look into the rich restaurant scene.

Accommodation in Poughkeepsie

Browse nearly 100 vacation rentals in Poughkeepsie, New York. With some rooms going for less than $100 per night, travelers with any budget can take a trip to this historic town. Plan your trip in the fall to see some spectacular foliage.

Transportation in Poughkeepsie

The nearest airport to Poughkeepsie is Stewart International Airport, about a 30-minute drive. There are two bus lines that operate within Poughkeepsie, and several Amtrak services that can take you to local destinations.

Vacation Rentals in Poughkeepsie

Find the best Poughkeepsie vacation rentals on Tripping.com. With over 33 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Poughkeepsie range from $49 a night. Many rentals can also be booked directly online.

Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 21 homes in Poughkeepsie offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 13 rentals with pool or jacuzzi, or relax with the family in one of the 20 homes with cable TV.

For all those pet owners with dogs or cats, Poughkeepsie offers 6 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com.

Search properties from 5 vacation rental sites in Poughkeepsie where the top providers in that area are Expedia, Booking.com, and HRS Holidays. There are 9 Expedia rentals, 8 Booking.com short term rentals and 6 HRS Holidays vacation rentals.