Downtown Poughkeepsie Vacation Packages
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Top Holiday Package Deals in Downtown Poughkeepsie
Price found within the past 48 hours. Click for updated prices.
Hilton Stamford Hotel & Executive Meeting Center
Waterside
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
7.4/10 Good! (1,008 reviews)
Very pleasant stay. Staff was kind and polite. Clean and comfortable room. We had a wonderful time
Reviewed on Aug. 3, 2025
Super 8 by Wyndham Middletown
per person
Oct 10 - Oct 15
found 8 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
6.2/10 (1,013 reviews)
The desk person on check in was fabulous. She really made a friend with my 10 yr old. She was super helpful and friendly. My only complaint was the shower curtain rod wasn't properly anchored. Had no effect on shower though. The 10 yr old loved the pattern on the bedspread.
Reviewed on Aug. 2, 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 Overlook Drive-In Theater or Frances Lehman Loeb Art Center.
Downtown Poughkeepsie Hotel Deals
DoubleTree by Hilton Poughkeepsie Convention Center
40 Civic Center Plz, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Aug 10 to Aug 11
CA $157
CA $184 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"Bathroom grout very dirty."
Reviewed on Aug. 1, 2025
The Crossroads Hotel, Newburgh
5 Lakeside Rd, Newburgh, NY
The price is CA $122 per night from Sep 4 to Sep 5
CA $122
CA $145 total
Sep 4 - Sep 5
includes taxes & fees
7.4/10 Good! (493 reviews)
"Pretty good"
Reviewed on Jul. 28, 2025
Holiday Inn Express Poughkeepsie by IHG
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is CA $150 per night from Aug 17 to Aug 18
CA $150
CA $174 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"The bathroom needed some work. The edges and corners have a lot of dirt build up"
Reviewed on Aug. 3, 2025
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.
Discover the most popular places to visit in Downtown Poughkeepsie
Eleanor Roosevelt National Historic Site
You can find out about the history of Haviland with a stop at Eleanor Roosevelt National Historic Site. While you're in the area, stroll along the riverfront.
Things to do
Llama/Alpaca Hike and Farm Tour
CA $92
per adult
100% of travellers recommend
Hudson Valley Wine and Food Day Trip with Sommelier host from NYC
CA $218
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.