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 $883, price is now CA $779 per person
CA $779
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newburgh (SWF)
9.4/10 Exceptional! (1,053 reviews)
Overall very nice place although breakfast was okay staff was wonderful clean place crowded
Reviewed on Apr 27, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $163 per night from Apr 30 to May 1
CA $163
CA $200 total
Apr 30 - May 1
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
The AC didn't work. It was a terrible night!
Reviewed on Apr 25, 2026
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
The price is CA $167 per night from May 4 to May 5
CA $167
CA $197 total
May 4 - May 5
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Was fine for the night.
Reviewed on Apr 28, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from May 18 to May 19
CA $162
CA $188 total
May 18 - May 19
includes taxes & fees
9/10 Wonderful! (1,110 reviews)
This place was excellent for a short stay. Staff were very courteous and efficient upon check-in. Room and facilities very clean, and location served me well.
Reviewed on Apr 28, 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.
