0 Bedrooms for 1 Guest
Price $10 - $1000+

107 Poughkeepsie Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Poughkeepsie holiday rentals from 5 rental sites including Booking.com, HomeAway, HRS Holidays, and more, ranging from $75 to $1800 a night. 
Showing 107 personalized results

    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

    Looking for the perfect vacation rental for your Poughkeepsie getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Poughkeepsie offers 107 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 38 properties with high-speed internet, 16 full with jacuzzi and pool, and NaN homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

    For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $4824 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Poughkeepsie has 107 gorgeous homes with 16 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

    Search properties from 5 rental sites in Poughkeepsie where the top providers in that area are Booking.com, HomeAway, and HRS Holidays. There are 55 Booking.com rentals, 29 HomeAway short term rentals and 13 HRS Holidays vacation rentals.