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 $744, price is now CA $744 per person
CA $744
per person
Jun 25 - Jun 28
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newburgh (SWF)
8.4/10 Very Good! (1,006 reviews)
Parking was great. Rooms were clean.
Reviewed on Apr 2, 2026
Sleep Inn & Suites Monroe - Woodbury
Price was CA $1,207, price is now CA $1,069 per person
CA $1,069
per person
Jun 25 - Jun 28
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newburgh (SWF)
9.4/10 Exceptional! (1,042 reviews)
Excellent property and in great condition
Reviewed on Mar 31, 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 $201 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 $159 per night from Apr 20 to Apr 21
CA $159
CA $185 total
Apr 20 - Apr 21
includes taxes & fees
9/10 Wonderful! (1,085 reviews)
Everything is fine
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 $138 per night from Apr 20 to Apr 21
CA $138
CA $160 total
Apr 20 - Apr 21
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.
