Downtown Poughkeepsie Vacations from $1,143
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The Latest Downtown Poughkeepsie Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Luxury NYC Home with Free Parking for 12
$1,143
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
2/10 (1 review)
THIS IS A SCAM!!! DO NOT BOOK THIS PROPERTY! NO ONE CAN GET IN TOUCH WITH THE OWNER AND EXPEDIA WOULD NOT HELP US FIND ALTERNATE ACCOMMODATIONS. WE GOT THERE WITH NO PLACE TO STAY AND HAD TO FIGURE IT OUT ON OUR OWN AND HAD TO PAY AGAIN. I NOW HAVE TO FIGHT WITH EXPEDIA TO GET MY MONEY BACK.
Reviewed on Oct 12, 2026
Modern Comfort in the Heart of NYC
Southeast Yonkers
$1,207
per person
Jan 10 - Jan 16
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to White Plains (HPN)
3.6/10 (4 reviews)
LIARS! these people take your money, when you go check in you'll find they aren't the real hosts. and house is already rented long term. NOT A TRUE LISTING!
Reviewed on Oct 14, 2026
Modern Luxury Home w GameRoom & Parking
Southeast Yonkers
$4,129
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
5/10 (12 reviews)
Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ...
Will use this management and property owner in our upcoming short terms rentals.....
Reviewed on Sep 13, 2026
Luxury NY Home with Free Parking
$2,333
per person
Dec 26 - Dec 30
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1 review)
Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine.
Reviewed on Nov 8, 2025
Where to stay in Downtown Poughkeepsie
Find the best Downtown Poughkeepsie areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Poughkeepsie
Arlington
1 out of top 10 points of interest in this area
You'll enjoy the coffeehouses and art galleries in Arlington. You might want to make time for a stop at Frances Lehman Loeb Art Center or Vassar Golf Course.
Poughkeepsie Waterfront
2 out of top 10 points of interest in this area
You'll enjoy the restaurants and riverfront in Poughkeepsie Waterfront. You might want to make time for a stop at Walkway Over the Hudson State Historic Park or Mid-Hudson Bridge.
Crown Heights
Visitors to Crown Heights enjoy its coffeehouses, and if you want to do some exploring, Hudson River is worth a stop.
Red Oaks Mill
The river views, waterfalls, and breweries are just a few things travelers enjoy about Red Oaks Mill. If you want to experience more of the area, check out Locust Grove or Poughkeepsie Galleria.
Union Street Historic District
When in Union Street Historic District, you can plan a visit to Mid-Hudson Civic Center and Bardavon 1869 Opera House, some noteworthy sights in the nearby area.
Downtown Poughkeepsie Hotel Deals
DoubleTree by Hilton Poughkeepsie Convention Center
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$110 nightly
$129 total
Oct 27 - Oct 28
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"Walking distance to train station and to the walkway across the Hudson and to a very good bbq brisket place. But the neighborhood is run down and the staff was not always helpful."
Reviewed on Oct 17, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$94 nightly
$109 total
Nov 15 - Nov 16
Total with taxes and fees
9/10 Wonderful! (1,124 reviews)
"Clean rooms, really helpfull Staff breakfast was amazing."
Reviewed on Oct 16, 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$152 nightly
$172 total
Nov 19 - Nov 20
Total with taxes and fees
8.2/10 Very Good! (1,010 reviews)
"I booked this stay over the NY Sheep and Wool festival weekend. I was confused when the receptionist started giving me directions to a building outside. The whole point was to stay in the historic hotel- not a bungalow outside. Anyway, we were there overnight. Dinner in the tavern was definitely ..."
Reviewed on Oct 18, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Downtown Poughkeepsie attractions
Chance Theater
8.0/10 (70 reviews)
Enjoy a show at Chance Theater, a storied theater in Poughkeepsie. Amble around the area's riverfront or attend a sporting event.
Mid-Hudson Civic Center
8.4/10 (79 reviews)
Mid-Hudson Civic Center is just one of the places to see in Poughkeepsie, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or attend a sporting event in the area.
Bardavon 1869 Opera House
9.2/10 (18 reviews)
Enjoy a performance at Bardavon 1869 Opera House, a theater with a story to tell in Poughkeepsie. Stroll along the riverfront or attend a sporting event in the area.
McCann Ice Arena
2.0/10 (1 review)
You can take time to visit McCann Ice Arena during your travels to Poughkeepsie. Stroll along the riverfront or attend a sporting event in the area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.