Search Deals onChester Vacation Packages
Chester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Middletown
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Stay at this motel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
The Crossroads Hotel, Newburgh
Save 100% on your flight
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Newburgh (SWF)
Stay at this 3-star business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Ice Time Sports Complex and Resorts World Hudson Valley are located nearby.
The Kartrite Resort & Indoor Waterpark
Save 100% on your flight
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Stay at this 4-star family-friendly hotel in Monticello. Enjoy 5 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Resorts World Catskills and Concord Monster Golf Course are located nearby.
Sleep Inn & Suites Middletown - Goshen
per person
May 23 - May 25
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 breakfast and the helpful staff in our reviews. Popular attractions Paramount Theatre and Soons Orchards are located nearby.
Courtyard by Marriott Newburgh Stewart Airport
per person
Jun 18 - Jun 21
found 10 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Ice Time Sports Complex and Resorts World Hudson Valley are located nearby.
Microtel Inn & Suites by Wyndham Middletown
per person
May 23 - May 25
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.
Resorts World Catskills Casino
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Stay at this 4.5-star luxury hotel in Monticello. Enjoy a full-service spa, 6 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Resorts World Catskills and Concord Monster Golf Course are located nearby.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport
per person
Apr 28 - May 1
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
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 rooms in our reviews. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley 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, May 1 - Sun, May 4
MCO
Orlando Intl.
SWF
Stewart Intl.
$122 Roundtrip, found 14 hours ago
$122
Roundtrip
found 14 hours ago
Tue, Apr 1 - Tue, Apr 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days ago
Thu, May 1 - Sun, May 4
MCO
Orlando Intl.
SWF
Stewart Intl.
$127 Roundtrip, found 14 hours ago
$127
Roundtrip
found 14 hours ago
Tue, Apr 1 - Tue, Apr 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$129 Roundtrip, found 3 days ago
$129
Roundtrip
found 3 days ago
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