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.
Courtyard by Marriott Newburgh Stewart Airport
Price was CA $667, price is now CA $593 per person
CA $593
per person
May 2 - May 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (708 reviews)
The room was very clean and spacious. This is one of the main reasons that I love booking at this location
Reviewed on Mar 8, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $858, price is now CA $769 per person
CA $769
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.4/10 Exceptional! (985 reviews)
Best hotel in town. Clean clean smoke free hotel
Reviewed on Feb 27, 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Price was CA $908, price is now CA $827 per person
CA $827
per person
May 12 - May 15
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Newburgh (SWF)
8.6/10 Excellent! (1,004 reviews)
Excellent location of hotel. The room was clean (no issues). From check-in to check out the staff was accommodating, courteous, friendly & helpful. Wi-Fi connected efficiently and breakfast was good. I believe guests would be satisfied staying at the hotel.
Reviewed on Mar 8, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $126 per night from Mar 22 to Mar 23
CA $126
CA $149 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Excellent location of hotel. The room was clean (no issues). From check-in to check out the staff was accommodating, courteous, friendly & helpful. Wi-Fi connected efficiently and breakfast was good. I believe guests would be satisfied staying at the hotel.
Reviewed on Mar 8, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Mar 29 to Mar 30
CA $148
CA $172 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (1,083 reviews)
A bit worn out room chair and desk area. Clean and very friendly front desk staff
Reviewed on Mar 11, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Apr 5 to Apr 6
CA $132
CA $153 total
Apr 5 - Apr 6
includes taxes & fees
8.4/10 Very Good! (1,125 reviews)
The cleanness of the hotel is disgusting. I would never recommend anyone to that hotel. It’s the worst and I mean the worst stuff no good the rooms no good even the toilet flood over so the cleanness and the staff is no good. I was so disappointed and disgusted of that Hotel.
Reviewed on Mar 9, 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.
