Search Deals onChester Vacation Packages
Chester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Newburgh/West Point
Price was $297, price is now $245 per person
$245
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
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. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
The Crossroads Hotel, Newburgh
Price was $501, price is now $390 per person
$390
per person
Dec 25 - Dec 30
found 2 hours ago
Roundtrip flight included
Chicago (ORD) to Newburgh (SWF)
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. Popular attractions Ice Time Sports Complex and Resorts World Hudson Valley are located nearby.
Sleep Inn & Suites Middletown - Goshen
Price was $433, price is now $358 per person
$358
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Paramount Theatre and Soons Orchards are located nearby.
Microtel Inn & Suites by Wyndham Middletown
Price was $421, price is now $349 per person
$349
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.
Ramada by Wyndham Newburgh/West Point
Price was $371, price is now $310 per person
$310
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
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 World Hudson Valley are located nearby.
Hampton Inn & Suites Newburgh Stewart Airport
Price was $537, price is now $451 per person
$451
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Hampton Inn by Hilton Middletown
Price was $418, price is now $356 per person
$356
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.
Super 8 by Wyndham Montgomery Maybrook
Price was $363, price is now $310 per person
$310
per person
Jan 3 - Jan 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Book a stay at this business-friendly motel in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions City Winery Hudson Valley and Orange County Farmers Museum are located nearby.
Chester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chester Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Dec 4 - Mon, Dec 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Thu, Dec 4 - Mon, Dec 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$161 Roundtrip, found 16 hours ago
$161
Roundtrip
found 16 hours ago
Thu, Dec 4 - Mon, Dec 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$173 Roundtrip, found 16 hours ago
$173
Roundtrip
found 16 hours ago
Thu, Dec 4 - Mon, Dec 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 12 hours ago
$183
Roundtrip
found 12 hours ago
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