Downtown Poughkeepsie Vacation Packages for 2026
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Downtown Poughkeepsie Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Amsterdam Hotel
Downtown Stamford
Price was $475, price is now $396 per person
$396
per person
Sep 10 - Sep 14
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stamford Town Center and Stamford Public Library - Ferguson Library are located nearby.
Tarrytown House Estate
Save 100% on your flight
Price was $875, price is now $641 per person
$641
per person
Sep 10 - Sep 14
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this business-friendly hotel in Tarrytown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Westchester County Center and Lyndhurst Mansion are located nearby.
Hampton Inn & Suites Yonkers
Northwest Yonkers
Price was $628, price is now $475 per person
$475
per person
Sep 10 - Sep 14
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Untermyer Gardens Conservancy and Legoland Discovery Center Westchester are located nearby.
Stamford Suites
Downtown Stamford
Price was $746, price is now $577 per person
$577
per person
Sep 10 - Sep 14
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this business-friendly aparthotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Stamford Public Library - Ferguson Library and Stamford Center for the Arts are located nearby.
Stamford Marriott Hotel & Spa
Downtown Stamford
Price was $873, price is now $688 per person
$688
per person
Sep 10 - Sep 14
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this spa hotel in Stamford. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Stamford Town Center and Stamford Center for the Arts are located nearby.
Hampton Inn White Plains/Tarrytown
Price was $622, price is now $510 per person
$510
per person
Sep 10 - Sep 14
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Westchester County Center and Westchester Skating Academy are located nearby.
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DoubleTree by Hilton Poughkeepsie Convention Center
40 Civic Center Plz Poughkeepsie NY
0.51 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Spark by Hilton Fishkill
20 Schuyler Blvd Fishkill NY
19.61 km from Downtown Poughkeepsie
Book a stay at this golf hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Best Western Plus Kingston Hotel And Conference Center
503 Washington Ave Kingston NY
27.58 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Kingston. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
The Crossroads Hotel, Newburgh
5 Lakeside Rd Newburgh NY
25.24 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
7.26 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Wildflower Farms, Auberge Collection
2702 Main St Gardiner NY
21.39 km from Downtown Poughkeepsie
Book a stay at this luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mohonk Preserve Visitor Center and Mohonk ...
Studio 6 Extended Stay Fishkill Route 9 NY
25 Merritt Blvd Fishkill NY
19.22 km from Downtown Poughkeepsie
Stay at this hotel in Fishkill. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Van Wyck Homestead Museum and Fishkill Golf Course ...
Ramada by Wyndham Newburgh/West Point
1289 Route 300 Newburgh NY
24.72 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a nightclub. Popular attractions Hamilton Fish Bridge and Resorts ...
Studio 6 Extended Stay Fishkill Westage Center NY
55 W Merritt Blvd Fishkill NY
19.59 km from Downtown Poughkeepsie
Stay at this hotel in Fishkill. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
25 OLD VINEYARD PLACE Hyde Park NY
4.75 km from Downtown Poughkeepsie
Stay at this hotel in Hyde Park. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. ...
Quality Inn & Suites Fishkill South near I-84
849 Route 52 Fishkill NY
19.39 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
5.27 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Highland. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Courtyard by Marriott Poughkeepsie
2641 South Road/Route 9 Poughkeepsie NY
3.61 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
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See all available properties in Downtown Poughkeepsie
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Aug 13 - Tue, Aug 18
MCO
Orlando Intl.
HPN
Westchester County
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Thu, Aug 13 - Tue, Aug 18
MCO
Orlando Intl.
HPN
Westchester County
$201 Roundtrip, found 5 days ago
$201
Roundtrip
found 5 days ago
Fri, Jun 19 - Tue, Jun 23
PBI
Palm Beach Intl.
HPN
Westchester County
$219 Roundtrip, found 5 days ago
$219
Roundtrip
found 5 days ago
Sat, Oct 31 - Tue, Nov 3
JAX
Jacksonville Intl.
HPN
Westchester County
$229 Roundtrip, found 6 days ago
$229
Roundtrip
found 6 days ago