Downtown Poughkeepsie Vacation Packages for 2026

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Top Hotel Deals

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
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

Spark by Hilton Fishkill

3 out of 5
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

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
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

The Crossroads Hotel, Newburgh

3 out of 5
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

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
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

Wildflower Farms, Auberge Collection

5 out of 5
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

Studio 6 Extended Stay Fishkill Route 9 NY

2.5 out of 5
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

Ramada by Wyndham Newburgh/West Point

2 out of 5
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

Studio 6 Extended Stay Fishkill Westage Center NY

2.5 out of 5
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

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
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

Quality Inn & Suites Fishkill South near I-84

2.5 out of 5
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

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
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

Courtyard by Marriott Poughkeepsie

3 out of 5
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 ...
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
24.97 km from Downtown Poughkeepsie
Book a stay at this business-friendly inn in Rhinebeck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave New Windsor NY
26.52 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
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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.

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.

Breeze Airways
Thu, Aug 13 - Tue, Aug 18
MCO
Orlando Intl.
HPN
Westchester County
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Aug 13 from Orlando Intl. to Westchester County, returning Tue, Aug 18, priced at $167 found 1 hour ago
Delta
Thu, Aug 13 - Tue, Aug 18
MCO
Orlando Intl.
HPN
Westchester County
$207 Roundtrip, found 1 hour ago
$207
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, Aug 13 from Orlando Intl. to Westchester County, returning Tue, Aug 18, priced at $207 found 1 hour ago
JetBlue Airways
Tue, Jul 14 - Sat, Jul 25
PBI
Palm Beach Intl.
HPN
Westchester County
$217 Roundtrip, found 5 hours ago
$217
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Tue, Jul 14 from Palm Beach Intl. to Westchester County, returning Sat, Jul 25, priced at $217 found 5 hours ago
American Airlines
Sat, Oct 31 - Tue, Nov 3
JAX
Jacksonville Intl.
HPN
Westchester County
$229 Roundtrip, found 6 days ago
$229
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Oct 31 from Jacksonville Intl. to Westchester County, returning Tue, Nov 3, priced at $229 found 6 days ago