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.
Sleep Inn & Suites Monroe - Woodbury
Price was CA $688, price is now CA $590 per person
CA $590
per person
May 24 - May 27
found 11 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
9.4/10 Exceptional! (1,046 reviews)
I was there for 1 night and didn’t do much just sleep for the night but it was pretty good.
Reviewed on Apr 9, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $144 per night from Apr 12 to Apr 13
CA $144
CA $170 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
As soon as I walked into the hotel I received a welcoming greeting and a smooth check-in. The room was very nice and clean. The beds were comfortable and the soap/shampoo/conditioner/lotion options provided were a nice touch. There was a variety of options for breakfast. From omelettes to pancakes, ...
Reviewed on Apr 9, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Apr 16 to Apr 17
CA $173
CA $202 total
Apr 16 - Apr 17
includes taxes & fees
9/10 Wonderful! (1,093 reviews)
Fabulous hotel and staff !!!
Reviewed on Apr 9, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Apr 21 to Apr 22
CA $142
CA $166 total
Apr 21 - Apr 22
includes taxes & fees
8.4/10 Very Good! (1,154 reviews)
Good
Reviewed on Apr 7, 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.
