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 $1,148, price is now CA $1,000 per person
CA $1,000
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 $165 per night from Apr 16 to Apr 17
CA $165
CA $195 total
Apr 16 - Apr 17
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Yes breafast fine
Reviewed on Apr 10, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Apr 26 to Apr 27
CA $158
CA $184 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (1,096 reviews)
Hot tub not working, the water was warm. The room furniture was in poor condition/damaged(I have pictures). My husband and I were very disappointed. We expected better considering the name Doubletree. The room had a very uncomfortable smell coming from the AC unit which became stronger when you turned ...
Reviewed on Apr 10, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Apr 26 to Apr 27
CA $134
CA $156 total
Apr 26 - Apr 27
includes taxes & fees
8.4/10 Very Good! (1,159 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.
