Chester Vacation Packages
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Your Chester Vacation
The exciting city of Chester is calling. Discover its hot spots and hidden treasures with a Chester vacation package that's customized to you. If taking in sights is on the agenda during your trip to Chester, swing by leading attractions like LEGOLAND® New York, The Rock Sports Complex and Goshen Historic Track. Don't delay visiting this destination any longer. Your ultimate Chester vacation is a couple of clicks away with Expedia.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Price was CA $571, price is now CA $565 per person
CA $565
per person
Jun 5 - Jun 7
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.4/10 Very Good! (1,006 reviews)
Parking was great. Rooms were clean.
Reviewed on Apr 2, 2026
Courtyard by Marriott Newburgh Stewart Airport
Price was CA $1,075, price is now CA $978 per person
CA $978
per person
Jun 20 - Jun 24
found 24 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.2/10 Very Good! (730 reviews)
I did not like the fact that you advertised a shuttle from the airport, but there was none
Reviewed on Mar 28, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $153 per night from Apr 12 to Apr 13
CA $153
CA $181 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
yes parking was good and breakfast was plentiful
Reviewed on Apr 4, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Apr 9 to Apr 10
CA $172
CA $200 total
Apr 9 - Apr 10
includes taxes & fees
9/10 Wonderful! (1,081 reviews)
Rooms need updating. Bed was comfortable.
Reviewed on Apr 3, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Apr 13 to Apr 14
CA $138
CA $160 total
Apr 13 - Apr 14
includes taxes & fees
8.4/10 Very Good! (1,148 reviews)
nice quiet location
Reviewed on Apr 2, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
