Search Deals onChester Vacation Packages
Chester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Middletown - Goshen
per person
May 8 - May 10
found 20 hours 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.
The Crossroads Hotel, Newburgh
Save 100% on your flight
per person
Jun 18 - Jun 23
found 18 hours 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.
Courtyard by Marriott Newburgh Stewart Airport
Save 100% on your flight
per person
May 2 - May 6
found 21 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 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.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
per person
May 25 - May 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Newburgh (SWF)
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 clean rooms in our reviews. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Holiday Inn Express & Suites Middletown - Goshen by IHG
per person
May 15 - May 18
found 2 hours ago
Roundtrip flight included
Savannah (SAV) 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.
Holiday Inn Express & Suites Montgomery by IHG
per person
May 15 - May 18
found 2 hours ago
Roundtrip flight included
Savannah (SAV) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions City Winery Hudson Valley and Orange County Farmers Museum are located nearby.
Home2 Suites by Hilton Middletown
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Newburgh (SWF)
Stay at this 3-star business-friendly hotel 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.
Courtyard by Marriott Middletown Goshen
per person
May 15 - May 18
found 2 hours ago
Roundtrip flight included
Savannah (SAV) to Newburgh (SWF)
Stay at this 3-star hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions LEGOLAND® New York and Galleria at Crystal Run 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 16 hours ago
$122
Roundtrip
found 16 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 4 days ago
$127
Roundtrip
found 4 days 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
Discover Other Travel Deals
- The Rock Sports Complex Vacations
- Castle Fun Center Vacations
- Goosepond Mountain State Park Vacations
- Museum Village Vacations
- LEGOLAND® New York Vacations
- Woodbury Common Premium Outlets Vacations
- Crystal Springs Golf Resort Vacations
- World Headquarters of Jehovah's Witnesses Vacations
- United States Military Academy Vacations
- Bear Mountain State Park Vacations
- Mountain Creek Ski Resort Vacations
- Dia Beacon Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
Car Rentals in Chester
- Car rentals in Pocono Mountains
- Car rentals in Upstate New York
- Car rentals in The Catskills
- Car rentals in Middletown
- Car rentals in Newburgh
- Car rentals in Wayne
- Car rentals in Vernon
- Car rentals in Fishkill
- Car rentals in New Paltz
- Car rentals in Beacon
- Car rentals in Hudson Valley
- Car rentals in Peekskill