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 ...
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
5.82 km from Downtown Poughkeepsie
Book a stay at this golf hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A Poughkeepsie NY
2.4 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 helpful staff and the clean ...
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
30.17 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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
26.27 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 ...
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 Tuthilltown Spirits and DM Weil Gallery ...
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
7.28 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 ...
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

2.5 out of 5
4 South Putt Corners Road New Paltz NY
12.66 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in New Paltz. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
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, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
95 Route 17K Newburgh NY
25.14 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Newburgh. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road Poughkeepsie NY
2.78 km from Downtown Poughkeepsie
Stay at this hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hampton Inn Kingston

Hampton Inn Kingston

2.5 out of 5
1307 Ulster Ave Kingston NY
30.27 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Minnewaska Lodge

Minnewaska Lodge

3 out of 5
3116 US-44 Gardiner NY
22.46 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Gardiner. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Homewood Suites by Hilton Poughkeepsie

Homewood Suites by Hilton Poughkeepsie

3 out of 5
900 Thomas Watson Dr Poughkeepsie NY
4.69 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 ...
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
Book a stay at this business-friendly hotel in Hyde Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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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.

JetBlue Airways
Thu, Dec 18 - Wed, Dec 31
MCO
Orlando Intl.
HPN
Westchester County
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, Dec 18 from Orlando Intl. to Westchester County, returning Wed, Dec 31, priced at $167 found 6 days ago
Breeze Airways
Thu, Feb 26 - Sun, Mar 1
MCO
Orlando Intl.
HPN
Westchester County
$186 Roundtrip, found 14 hours ago
$186
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Thu, Feb 26 from Orlando Intl. to Westchester County, returning Sun, Mar 1, priced at $186 found 14 hours ago
Delta
Thu, Feb 26 - Sun, Mar 1
MCO
Orlando Intl.
HPN
Westchester County
$207 Roundtrip, found 14 hours ago
$207
Roundtrip
found 14 hours ago
Select Delta flight, departing Thu, Feb 26 from Orlando Intl. to Westchester County, returning Sun, Mar 1, priced at $207 found 14 hours ago
American Airlines
Thu, Feb 26 - Sun, Mar 1
MCO
Orlando Intl.
HPN
Westchester County
$217 Roundtrip, found 14 hours ago
$217
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Thu, Feb 26 from Orlando Intl. to Westchester County, returning Sun, Mar 1, priced at $217 found 14 hours ago