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.
Sleep Inn & Suites Monroe - Woodbury
Price was CA $585, price is now CA $549 per person
CA $549
per person
May 11 - May 14
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
9.4/10 Exceptional! (1,035 reviews)
Nice and clean. Good breakfast. Staff was friendly.
Reviewed on Mar 5, 2026
Courtyard by Marriott Newburgh Stewart Airport
Price was CA $817, price is now CA $730 per person
CA $730
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
8.2/10 Very Good! (707 reviews)
Convenient location and great staff. The assigned room was clean and comfortable, but the bathroom door would not shut properl.
Reviewed on Mar 2, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $1,158, price is now CA $1,052 per person
CA $1,052
per person
Apr 9 - Apr 14
found 19 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newburgh (SWF)
9.4/10 Exceptional! (980 reviews)
Best hotel in town. Clean clean smoke free hotel
Reviewed on Feb 27, 2026
Hampton Inn & Suites Newburgh Stewart Airport
Price was CA $627, price is now CA $594 per person
CA $594
per person
May 11 - May 14
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
9.2/10 Wonderful! (1,000 reviews)
The lady at the front desk at check-in was fantastic. Friendly and answered any questions we had
Reviewed on Mar 1, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $117 per night from Mar 8 to Mar 9
CA $117
CA $139 total
Mar 8 - Mar 9
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
The rooms were amazing and staff was so accommodating....
Reviewed on Feb 27, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Mar 8 to Mar 9
CA $132
CA $154 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (1,111 reviews)
Clean room, very accessible location, close to shopping, restaurants, and highways. Good value for the price.
Reviewed on Mar 1, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Mar 9 to Mar 10
CA $154
CA $182 total
Mar 9 - Mar 10
includes taxes & fees
9.4/10 Exceptional! (983 reviews)
Clean the staff is very nice
Reviewed on Mar 1, 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.
