Chester Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Chester Vacation Packages

Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place Chester NY
Fully refundable
The price is ￥18,604 per night from Jul 2 to Jul 3
￥18,604
￥22,908 total
Jul 2 - Jul 3
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"The rooms were large, staff was friendly and complimentary breakfast had a large variety of food."

Reviewed on Jun 24, 2026

Holiday Inn Express Hotel & Suites Chester by IHG
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is ￥22,076 per night from Jul 2 to Jul 3
￥22,076
￥27,182 total
Jul 2 - Jul 3
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"We stayed in the Overlook Lodge. There are no staff members in attendance -- you must check in a half mile away at the Inn. You need your room key to get into the lobby of the lodge day or night. Our room was on the second floor -- it was only accessible by a long flight of stairs. Don't bring a ..."

Reviewed on Jun 25, 2026

Overlook Lodge at Bear Mountain
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
The price is ￥19,825 per night from Jun 29 to Jun 30
￥19,825
￥23,420 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (1,042 reviews)
"Clean room loved my stay with my family the kids enjoy the pool a lot of things close by to do too…"

Reviewed on Jun 25, 2026

Sleep Inn & Suites Middletown - Goshen
See all 1,082 properties in Chester
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.

Stay near popular Chester attractions

The Rock Sports Complex

8.0/5 (18 reviews)
This dedicated sports venue hosts baseball and softball tournaments on well-maintained turf fields. Bring portable chairs and sun protection to enjoy the games in comfort at this local athletic hub.
See properties

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.