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 $499, price is now CA $492 per person
CA $492
per person
May 16 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 $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! (1,000 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 $168 per night from Apr 21 to Apr 22
CA $168
CA $195 total
Apr 21 - Apr 22
includes taxes & fees
9/10 Wonderful! (1,089 reviews)
Recently stayed for a quick overnight. Staff was friendly and accommodating. The room was a bit more used than expected (wear and tear on the furniture and decor). The room was fine for an overnight but looked across into the indoor pool area, so blinds needed to be closed. The larger advertised ...
Reviewed on Apr 8, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from May 3 to May 4
CA $152
CA $177 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (1,153 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.
