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.
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $185 per night from May 3 to May 4
CA $185
CA $218 total
May 3 - May 4
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
I stayed with my 3 kids. Room Was clean, staff was very pleasant. Breakfast was very good.
Reviewed on Apr 20, 2026
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
The price is CA $142 per night from Apr 26 to Apr 27
CA $142
CA $167 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Yes, food was fresh and parking was easy. Only had trouble charging our smart watches during the day. Very odd sitituation. Staff did their best to help us out.
Reviewed on Apr 22, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from May 18 to May 19
CA $159
CA $185 total
May 18 - May 19
includes taxes & fees
9/10 Wonderful! (1,105 reviews)
Everything was great
Reviewed on Apr 21, 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.
