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.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Price was CA $969, price is now CA $904 per person
CA $904
per person
May 11 - May 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.4/10 Very Good! (1,006 reviews)
Parking was great. Rooms were clean.
Reviewed on Apr 2, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $170 per night from Apr 12 to Apr 13
CA $170
CA $200 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (1,003 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 $153 per night from Apr 26 to Apr 27
CA $153
CA $178 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (1,087 reviews)
Everything was perfect for me ♾️
Reviewed on Apr 6, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Apr 30 to May 1
CA $143
CA $167 total
Apr 30 - May 1
includes taxes & fees
8.4/10 Very Good! (1,151 reviews)
Love the kitchen in the room.
Reviewed on Apr 5, 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.
