16 Poughkeepsie Holiday Rentals

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Compare Poughkeepsie holiday rentals from 5 rental sites including Booking.com, HomeAway, HRS Holidays and more, ranging from $63 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

Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Poughkeepsie offers 114 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $268 a night, or a long-term rental for an average price of $5572 a month.

These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 39 of Poughkeepsie’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 17 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 100 cozy homes.

Traveling with pets? Choose from 16 pet-friendly rentals in Poughkeepsie for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

Search properties from 5 rental sites in Poughkeepsie where the top providers in that area are Booking.com, HomeAway, and HRS Holidays. There are 59 Booking.com rentals, 29 HomeAway short term rentals and 15 HRS Holidays vacation rentals.
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