
Chester Vacations from ¥230,850
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 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
The Latest Chester Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Price was ¥238,200, price is now ¥230,850 per person
¥230,850
per person
May 13 - May 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newburgh (SWF)
8.4/10 Very Good! (1,011 reviews)
The pillows in the room and the heating system wasnt controlable and it was a little cold
Reviewed on Mar 2, 2026

Homewood Suites Stewart Airport
Price was ¥312,180, price is now ¥299,062 per person
¥299,062
per person
May 13 - May 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newburgh (SWF)
9.2/10 Wonderful! (1,001 reviews)
Didn't have a mountain view. Room was clean and up to my standards. Indoor pool was clean and busy. The food isn't what it used to be. No more waffle makers and not everyone cares for the taco stuff. I'm one of them. Also, had the same scrambled eggs and tater rounds every day. Not impressed with this change.
Reviewed on Mar 25, 2026
Find the Best Chester Vacation Packages
Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
The price is ¥20,243 per night from Mar 31 to Apr 1
¥20,243
¥23,912 total
Mar 31 - Apr 1
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 ¥19,234 per night from Apr 9 to Apr 10
¥19,234
¥22,385 total
Apr 9 - Apr 10
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 ¥16,223 per night from Apr 23 to Apr 24
¥16,223
¥18,879 total
Apr 23 - Apr 24
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.
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.
