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 ...
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 ...
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 ...
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 ...
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 ...
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 WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast 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 ...
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. ...
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 ...
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 ...
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 ...
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 family-friendly hotel in Kingston. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful ...
Beekman Arms Hotel

Beekman Arms Hotel

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. ...
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

3 out of 5
25 Westage Road Fishkill NY
19.64 km from Downtown Poughkeepsie
Book a stay at this business-friendly hotel in Fishkill. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
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.

JetBlue Airways
Tue, Mar 3 - Sat, Mar 7
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$152 Roundtrip, found 5 days ago
$152
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Mar 3 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sat, Mar 7, priced at $152 found 5 days ago
American Airlines
Wed, Mar 4 - Mon, Mar 9
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Mar 4 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Mon, Mar 9, priced at $171 found 5 days ago
Delta
Thu, Mar 5 - Sun, Mar 8
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$174 Roundtrip, found 5 days ago
$174
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Mar 5 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sun, Mar 8, priced at $174 found 5 days ago
Breeze Airways
Thu, Feb 26 - Sun, Mar 1
MCO
Orlando Intl.
HPN
Westchester County
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Feb 26 from Orlando Intl. to Westchester County, returning Sun, Mar 1, priced at $190 found 2 days ago