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 $1,023, price is now CA $994 per person
CA $994
per person
Apr 30 - May 3
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Newburgh (SWF)
8.4/10 Very Good! (1,011 reviews)
Convenient, clean and friendly..
Reviewed on Mar 27, 2026
Hampton Inn & Suites Newburgh Stewart Airport
Price was CA $1,200, price is now CA $1,142 per person
CA $1,142
per person
May 28 - Jun 1
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.2/10 Wonderful! (1,011 reviews)
it was an amazing stay everyone was nice , having someone disabled with me the amenities were nice! recommend always!!
Reviewed on Mar 27, 2026
Sleep Inn & Suites Monroe - Woodbury
Price was CA $1,160, price is now CA $1,133 per person
CA $1,133
per person
Apr 30 - May 4
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Newburgh (SWF)
9.4/10 Exceptional! (1,042 reviews)
I was very happy with my stay. Room was really clean. Great blankets, big and comfy. Breakfast was a wide variety with name brand choices. Not no name brands and plenty to chose from. Fresh baked cookies when I came in around 7pm
Reviewed on Mar 22, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $172 per night from Apr 1 to Apr 2
CA $172
CA $203 total
Apr 1 - Apr 2
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
Parking was easy- lady at the front desk was great. Room was good
Reviewed on Mar 23, 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 6 to Apr 7
CA $158
CA $184 total
Apr 6 - Apr 7
includes taxes & fees
9/10 Wonderful! (1,079 reviews)
Everything was great. Customer service was genuine and welcoming!!
Reviewed on Mar 23, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Apr 5 to Apr 6
CA $135
CA $157 total
Apr 5 - Apr 6
includes taxes & fees
8.4/10 Very Good! (1,142 reviews)
the room was clean and kinda quit. Good location
Reviewed on Mar 27, 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.
