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.
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $946, price is now CA $864 per person
CA $864
per person
May 3 - May 6
found 12 hours ago
Roundtrip flight included
Vancouver (YVR) to Newburgh (SWF)
9.4/10 Exceptional! (985 reviews)
Best hotel in town. Clean clean smoke free hotel
Reviewed on Feb 27, 2026
Sleep Inn & Suites Monroe - Woodbury
Price was CA $1,501, price is now CA $1,399 per person
CA $1,399
per person
Jun 7 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newburgh (SWF)
9.4/10 Exceptional! (1,042 reviews)
Wonderful staff, clean and perfect for family, business or leisure stay. And budget friendly.
Reviewed on Mar 19, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $128 per night from Mar 22 to Mar 23
CA $128
CA $151 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Yes
Reviewed on Mar 16, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Mar 29 to Mar 30
CA $141
CA $165 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (1,076 reviews)
Great stay! Clean, friendly and accommodating!
Reviewed on Mar 19, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Mar 29 to Mar 30
CA $133
CA $155 total
Mar 29 - Mar 30
includes taxes & fees
8.4/10 Very Good! (1,134 reviews)
.
Reviewed on Mar 18, 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.
