17 Poughkeepsie Vacation Rentals & Short Term Rentals

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Compare Poughkeepsie vacation rentals from 6 rental sites including Booking.com, HomeAway, HRS Holidays and more, ranging from $50 to $1500 a night.
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Information about Poughkeepsie

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 with Tripping.com. Choose from 121 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $50 a night to $1500 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 44 of homes in Poughkeepsie offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 20 rentals with pool or jacuzzi, or relax with the family in one of the 42 homes with cable TV.

For all those dog lovers and cat lovers, Poughkeepsie offers 18 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 6 rental sites in Poughkeepsie where the top providers in that area are Booking.com, HomeAway, and HRS Holidays. There are 58 Booking.com rentals, 29 HomeAway short term rentals and 15 HRS Holidays vacation rentals.
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