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.
Courtyard by Marriott Newburgh Stewart Airport
Price was CA $613, price is now CA $540 per person
CA $540
per person
Apr 27 - Apr 30
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (712 reviews)
Older room with chemical cleaning solution smell
Reviewed on Mar 24, 2026
Sleep Inn & Suites Middletown - Goshen
Price was CA $825, price is now CA $718 per person
CA $718
per person
May 8 - May 11
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
8.6/10 Excellent! (1,015 reviews)
Clean room, safe and staff is courteous
Reviewed on Mar 19, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $854, price is now CA $787 per person
CA $787
per person
May 9 - May 12
found 19 hours ago
Roundtrip non-stop 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
The Lagrange Inn & Extended Stay
Price was CA $795, price is now CA $733 per person
CA $733
per person
May 8 - May 11
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
9.4/10 Exceptional! (13 reviews)
The room was freezing cold for about a half hour when we got there but the heater worked well and eventually it warmed up. Room was large and clean. Parking was right in front of room. Wish the room had a full length mirror. People travel when they have an event to go to and we like to see how we look. The bathroom mirror sort of tilts down for a bit of an outfit check but a full length would have been great. Bed was comfortable and bedding was really nice! Guy who runs the place was very nice! Easy check in with digital code and no need for a front desk visit. We would stay again if in the area.
Reviewed on Jan 8, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $173 per night from Mar 26 to Mar 27
CA $173
CA $205 total
Mar 26 - Mar 27
includes taxes & fees
8.6/10 Excellent! (1,001 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 $170 per night from Apr 21 to Apr 22
CA $170
CA $198 total
Apr 21 - Apr 22
includes taxes & fees
9/10 Wonderful! (1,082 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 $141 per night from Apr 7 to Apr 8
CA $141
CA $164 total
Apr 7 - Apr 8
includes taxes & fees
8.4/10 Very Good! (1,141 reviews)
Clean, large room. Comfortable bed.
Reviewed on Mar 25, 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.
