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 1 hour 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 $169 per night from Apr 12 to Apr 13
CA $169
CA $200 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
The breakfast was amazing and staff friendly. However this hotel is under construction and paint fumes in the halls. Thankfully not in the room. The dust from the construction was in the rooms. Vacuuming the carpet would’ve been a good idea. After construction I’m sure this hotel would merit 5 ...
Reviewed on Apr 6, 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 20 to Apr 21
CA $158
CA $184 total
Apr 20 - Apr 21
includes taxes & fees
9/10 Wonderful! (1,092 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 23 to Apr 24
CA $142
CA $165 total
Apr 23 - Apr 24
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.
