Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 Monroe - Woodbury
Price was CA $1,115, price is now CA $975 per person
CA $975
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Newburgh (SWF)
9.4/10 Exceptional! (1,060 reviews)
Clean room, the staff was nice and the breakfast was surprisingly good. The kids loved the waffle maker. Good place to crash for a night.
Reviewed on May 1, 2026
Chester Hotel Deals
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is CA $143 per night from May 3 to May 4
CA $143
CA $176 total
May 3 - May 4
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
The AC didn't work. It was a terrible night!
Reviewed on Apr 25, 2026
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
The price is CA $167 per night from May 5 to May 6
CA $167
CA $197 total
May 5 - May 6
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Great breakfast
Reviewed on May 1, 2026
DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from May 18 to May 19
CA $162
CA $188 total
May 18 - May 19
includes taxes & fees
9/10 Wonderful! (1,110 reviews)
Completely not relaxing, hot tub was disgusting and staff was not accommodating and they did not allow my service animal although I booked online a more expensive room, they wanted me to stay in the first floor room which were designated for any pet… This is illegal in the state of New Jersey, New ...
Reviewed on Apr 30, 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.
