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 3 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 $889, price is now CA $843 per person
CA $843
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 $140 per night from Mar 29 to Mar 30
CA $140
CA $163 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (1,080 reviews)
Excellent!!!
Reviewed on Mar 17, 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 Apr 12 to Apr 13
CA $133
CA $155 total
Apr 12 - Apr 13
includes taxes & fees
8.4/10 Very Good! (1,136 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.
