Downtown Poughkeepsie Vacation Packages for 2025

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Downtown Poughkeepsie Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
per person
Oct 1 - Oct 6
found 17 hours ago
Roundtrip flight included
Orange County (SNA) to Newburgh (SWF)
Stay at this motel in Middletown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
per person
Oct 1 - Oct 6
found 17 hours ago
Roundtrip flight included
Orange County (SNA) to White Plains (HPN)
Stay at this 3-star business-friendly vacation home in Yonkers. Enjoy free WiFi, free parking, and dry cleaning or laundry services. Popular attractions Bronx Zoo and Yonkers Raceway are located nearby.

Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
Save 100% on your flight
per person
Oct 1 - Oct 6
found 17 hours ago
Roundtrip flight included
Orange County (SNA) to White Plains (HPN)
Stay at this 4-star vacation home in Yonkers. Enjoy free WiFi, laundry facilities, and a picnic area. Popular attractions Bronx Zoo and Yonkers Raceway are located nearby.

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
Arlington
per person
Oct 8 - Oct 12
found 17 hours ago
Roundtrip flight included
Orange County (SNA) to White Plains (HPN)
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 rooms in our reviews. Popular attractions Frances Lehman Loeb Art Center and Vassar Golf Course are located nearby.

Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 out of 5
per person
Oct 8 - Oct 12
found 17 hours ago
Roundtrip flight included
Orange County (SNA) to White Plains (HPN)
Stay at this 3.5-star business-friendly apartment in White Plains. Enjoy free WiFi, an outdoor pool, and valet parking (surcharge). Popular attractions Galleria at White Plains and Westchester County Center are located nearby.

Hilton Stamford Hotel & Executive Meeting Center

Hilton Stamford Hotel & Executive Meeting Center

3.5 out of 5
Waterside
per person
Oct 8 - Oct 12
found 17 hours ago
Roundtrip flight included
Orange County (SNA) to White Plains (HPN)
Stay at this 3.5-star business-friendly hotel in Stamford. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Museum of Black World War II History and Stamford Center for the Arts are located nearby.

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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 ...
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. ...
Wingate by Wyndham Fishkill

Wingate by Wyndham Fishkill

3 out of 5
20 Schuyler Blvd, Fishkill, NY
19.61 km from Downtown Poughkeepsie
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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 ...
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 ...
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 3-star business-friendly hotel in Hyde Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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 ...
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 ...
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
19.47 km from Downtown Poughkeepsie
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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 ...
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. ...
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 ...
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 ...
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
1287 Route 300, Newburgh, NY
24.73 km from Downtown Poughkeepsie
Book a stay at this business-friendly motel in Newburgh. 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 6 - Sat, Sep 13
PBI
Palm Beach Intl.
HPN
Westchester County
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Sep 6 from Palm Beach Intl. to Westchester County, returning Sat, Sep 13, priced at $167 found 2 days ago
Breeze Airways
Tue, Aug 12 - Sat, Aug 16
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 6 days ago
$183
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Aug 12 from Orlando Intl. to Stewart Intl., returning Sat, Aug 16, priced at $183 found 6 days ago
American Airlines
Tue, Sep 9 - Tue, Sep 16
PBI
Palm Beach Intl.
HPN
Westchester County
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 9 from Palm Beach Intl. to Westchester County, returning Tue, Sep 16, priced at $187 found 2 days ago
Delta
Tue, Aug 12 - Sat, Aug 23
TPA
Tampa Intl.
HPN
Westchester County
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 12 from Tampa Intl. to Westchester County, returning Sat, Aug 23, priced at $197 found 6 days ago