Chester County Vacations & Trips

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Your Chester County Vacation

Leave the planning up to us with a Chester County vacation package. With everything organized before you head off, the only thing left for you to do is relax and experience this destination's beauty and culture. A trip to Chester County offers so much to see and do. Not sure where to begin your travels? Henderson is one of the most popular cities to stay here. From the moment you book your Chester County vacation to the second you come back home, Expedia has your back every step of the way.

Find the Best Chester County Vacation Packages

Chester County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
McKellar-Sipes Regional Airport (MKL)
Top Sights
Chickasaw State Park, Chickasaw State Park and Chickasaw Golf Course

Chester County Hotel Deals

Americana Inn

Americana Inn

2.5 out of 5
550 Sanford St Henderson TN
$72 nightly
The price is $82 total per night from Nov 9 to Nov 10
$82 total
Nov 9 - Nov 10
Total with taxes and fees
Americana Inn
Wingate By Wyndham Jackson

Wingate By Wyndham Jackson

3 out of 5
2370 N Highland Ave South Jackson TN
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $87 total per night from Nov 15 to Nov 16
$87 total
Nov 15 - Nov 16
Total with taxes and fees
9.2/10 Wonderful! (386 reviews)
"Clean room Good breakfast"

Reviewed on Nov 5, 2026

Wingate By Wyndham Jackson
Sleep Inn & Suites Savannah Tennessee Riverfront

Sleep Inn & Suites Savannah Tennessee Riverfront

2.5 out of 5
105 Million Dollar Way Savannah TN
Fully refundable
$94 nightly
The price is $112 total per night from Dec 6 to Dec 7
$112 total
Dec 6 - Dec 7
Total with taxes and fees
Sleep Inn & Suites Savannah Tennessee Riverfront
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 County attractions

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.