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 Middletown - Goshen
Price was CA $770, price is now CA $683 per person
CA $683
per person
May 1 - May 4
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.6/10 Excellent! (1,006 reviews)
The tvs are pretty outdated. Wish it at least had Netflix. But overall the room was clean and not a bad spot to stay if you need to chill for a night or two. Gets the job done. Breakfast options were kinda limited but at least the offer it complimentary.
Reviewed on Mar 4, 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Price was CA $886, price is now CA $773 per person
CA $773
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.6/10 Excellent! (1,002 reviews)
The rooms were amazing and staff was so accommodating....
Reviewed on Feb 27, 2026
Courtyard by Marriott Newburgh Stewart Airport
Price was CA $971, price is now CA $857 per person
CA $857
per person
May 1 - May 4
found 21 hours ago
Roundtrip flight included
Montreal (YUL) 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 $853, price is now CA $780 per person
CA $780
per person
May 1 - May 4
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
9.4/10 Exceptional! (980 reviews)
Best hotel in town. Clean clean smoke free hotel
Reviewed on Feb 27, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
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! (1,005 reviews)
The rooms were amazing and staff was so accommodating....
Reviewed on Feb 27, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Mar 22 to Mar 23
CA $144
CA $168 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (1,074 reviews)
The pool and hot tub were very enjoyable
Reviewed on Mar 5, 2026
Sonesta Simply Suites Nanuet
20 Overlook Blvd Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Mar 8 to Mar 9
CA $128
CA $149 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (1,112 reviews)
Clean room, very accessible location, close to shopping, restaurants, and highways. Good value for the price.
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.
