Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 $727, price is now CA $623 per person
CA $623
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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The tvs are pretty outdated.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
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $829, price is now CA $725 per person
CA $725
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.4/10 Exceptional! (980 reviews)
Best hotel in town. Clean clean smoke free hotel
Reviewed on Feb 27, 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Price was CA $739, price is now CA $669 per person
CA $669
per person
May 19 - May 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
8.6/10 Excellent! (1,004 reviews)
The rooms were amazing and staff was so accommodating....
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 $126 per night from Mar 22 to Mar 23
CA $126
CA $149 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 19 to Mar 20
CA $144
CA $167 total
Mar 19 - Mar 20
includes taxes & fees
9/10 Wonderful! (1,075 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 $132 per night from Mar 15 to Mar 16
CA $132
CA $153 total
Mar 15 - Mar 16
includes taxes & fees
8.4/10 Very Good! (1,117 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
