Find Vacation Rentals in Poughkeepsie

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Popular Poughkeepsie Vacation Rentals

Find the perfect Poughkeepsie vacation rental

House Poughkeepsie
from $526 per night
House ∙ 6 guests ∙ 3 bedrooms

247 m² House

5.0
Outstanding(33 ratings)
Poughkeepsie, Dutchess County, New York, United States
Details
Farmhouse Poughkeepsie
from $357 per night
10 guests ∙ 4 bedrooms

Farmhouse

4.9
Outstanding(30 ratings)
Poughkeepsie, Dutchess County, New York, United States
Details
House Poughkeepsie
from $324 per night
House ∙ 6 guests ∙ 3 bedrooms

135 m² House

5.0
Outstanding(5 ratings)
Poughkeepsie, Dutchess County, New York, United States
Details
House Poughkeepsie
from $190 per night
3 guests ∙ 1 bedroom

House

4.6
Excellent(15 ratings)
Poughkeepsie, Dutchess County, New York, United States
Details
House Poughkeepsie
from $1,242 per night
House ∙ 10 guests ∙ 5 bedrooms

376 m² House

5.0
Outstanding(8 ratings)
Poughkeepsie, Dutchess County, New York, United States
Details
House Poughkeepsie
from $1,454 per night
House ∙ 8 guests ∙ 4 bedrooms

372 m² House

4.9
Outstanding(14 ratings)
Poughkeepsie, Dutchess County, New York, United States
Details
Condo Poughkeepsie
from $132 per night
4 guests ∙ 1 bedroom

Condo

4.9
Outstanding(41 ratings)
Poughkeepsie, Dutchess County, New York, United States
Details
House Poughkeepsie
from $215 per night
4 guests ∙ 2 bedrooms

House

3.4
(10 ratings)
Poughkeepsie, Dutchess County, New York, United States
Details
House Poughkeepsie
from $336 per night
18 guests ∙ 5 bedrooms

House

5.0
Outstanding(3 ratings)
Poughkeepsie, Dutchess County, New York, United States
Details
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Vacation rentals and apartments with air conditioning

House  Poughkeepsie
from $139 per night
4 guests ∙ 3 bedrooms

House

Poughkeepsie, Dutchess County, New York, United States
Air conditioning
Details
Cabin  Poughkeepsie
from $344 per night
2 guests ∙ 1 bedroom

Cabin

5.0
Outstanding(1 rating)
Poughkeepsie, Dutchess County, New York, United States
Air conditioning
Details
House  Poughkeepsie
from $658 per night
7 guests ∙ 3 bedrooms

House

Poughkeepsie, Dutchess County, New York, United States
Air conditioning
Details
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Cabins and Homes With Fireplaces

House  Poughkeepsie
from $605 per night
8 guests ∙ 4 bedrooms

House

4.7
Excellent(42 ratings)
Poughkeepsie, Dutchess County, New York, United States
Fireplace
Details
Villa  Poughkeepsie
from $845 per night
Villa ∙ 10 guests ∙ 4 bedrooms

411 m² Villa

4.7
Excellent(28 ratings)
Poughkeepsie, Dutchess County, New York, United States
Fireplace
Details
Cabin  Poughkeepsie
from $230 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

93 m² Cabin

5.0
Outstanding(32 ratings)
Poughkeepsie, Dutchess County, New York, United States
Fireplace
Details
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Apartments and vacation rentals with a kitchen

Apartment  Poughkeepsie
from $142 per night
4 guests ∙ 1 bedroom

Apartment

Poughkeepsie, Dutchess County, New York, United States
Kitchen
Details
Apartment  Poughkeepsie
from $164 per night
2 guests ∙ 1 bedroom

Apartment

Poughkeepsie, Dutchess County, New York, United States
Kitchen
Details
House  Poughkeepsie
from $198 per night
4 guests ∙ 2 bedrooms

House

Poughkeepsie, Dutchess County, New York, United States
Kitchen
Details
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Frequently Asked Questions

How much does it cost to book a vacation rental in Poughkeepsie?

In Poughkeepsie, vacation rentals start at $139 per night.

Are there any vacation rentals available to book in Poughkeepsie?

Currently, there are 214 vacation rentals available for you to compare and book.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

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.

Popular Day Trips Near Poughkeepsie

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