Downtown Poughkeepsie Vacation Packages for 2025

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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
Stay at this 4-star business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
21.39 km from Downtown Poughkeepsie
Stay at this 5-star luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mohonk Lake and Tuthilltown Spirits are ...
Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

2 out of 5
7 Terwilliger Ln, New Paltz, NY
12.64 km from Downtown Poughkeepsie
Book a stay at this business-friendly motel in New Paltz. 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 ...
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
25.24 km from Downtown Poughkeepsie
Stay at this 3-star business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
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 breakfast, free parking, and room service. Our guests praise the breakfast and the helpful ...
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 breakfast and the helpful staff ...
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
Stay at this 3-star business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

2.5 out of 5
4142 Albany Post Rd, Hyde Park, NY
8.02 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 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 ...
Super 8 by Wyndham Kingston

Super 8 by Wyndham Kingston

2.5 out of 5
487 Washington Ave, Kingston, NY
27.56 km from Downtown Poughkeepsie
Book a stay at this business-friendly motel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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. ...
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, I-87 Exit 18 to I-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 ...
Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

3 out of 5
2619 South Road, Poughkeepsie, NY
3.82 km from Downtown Poughkeepsie
Stay at this 3-star business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Locust Grove and McCann Golf ...
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 ...
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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
Sat, Sep 20 - Fri, Oct 3
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$107 Roundtrip, found 5 days ago
$107
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Sep 20 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Fri, Oct 3, priced at $107 found 5 days ago
American Airlines
Mon, Sep 22 - Mon, Oct 6
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$138 Roundtrip, found 5 days ago
$138
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Sep 22 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Mon, Oct 6, priced at $138 found 5 days ago
Breeze Airways
Fri, Dec 5 - Mon, Dec 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 5 from Orlando Intl. to Stewart Intl., returning Mon, Dec 8, priced at $157 found 1 day ago
Delta
Mon, Sep 22 - Mon, Oct 6
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Sep 22 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Mon, Oct 6, priced at $177 found 5 days ago