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.
Wildflower Farms, Auberge Collection
Price was CA $4,609, price is now CA $3,874 per person
CA $3,874
per person
May 18 - May 21
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Newburgh (SWF)
9.4/10 Exceptional! (61 reviews)
Everything was ok, except for the fact that we couldn’t do late check out or that we payed a bit more for a standard room. But everything else was perfect
Reviewed on Dec 13, 2025
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $986, price is now CA $895 per person
CA $895
per person
Apr 19 - Apr 23
found 18 hours ago
Roundtrip flight included
Calgary (YYC) to Newburgh (SWF)
9.4/10 Exceptional! (985 reviews)
Best hotel in town. Clean clean smoke free hotel
Reviewed on Feb 27, 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Price was CA $852, price is now CA $796 per person
CA $796
per person
Apr 23 - Apr 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.4/10 Very Good! (1,011 reviews)
The pillows in the room and the heating system wasnt controlable and it was a little cold
Reviewed on Mar 2, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
The price is CA $127 per night from Mar 22 to Mar 23
CA $127
CA $150 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Yes
Reviewed on Mar 16, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Mar 29 to Mar 30
CA $145
CA $169 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (1,080 reviews)
Excellent!!!
Reviewed on Mar 17, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Mar 22 to Mar 23
CA $133
CA $155 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (1,136 reviews)
.
Reviewed on Mar 18, 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.
