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
550 Sanford St Henderson TN
$76 nightly
$88 total
Sep 24 - Sep 25
Total with taxes and fees
7.6/10 Good! (390 reviews)
"We really enjoyed our stay. The manager was very nice and helpful. It's very quiet and peaceful. Our room was good. The air-conditioning worked very well. The room was clean. The only issue I had was that the mattress was a little too firm."
Reviewed on Sep 13, 2026
Sleep Inn & Suites Savannah Tennessee Riverfront
105 Million Dollar Way Savannah TN
Fully refundable
$103 nightly
$124 total
Oct 11 - Oct 12
Total with taxes and fees
9.2/10 Wonderful! (109 reviews)
"Wonderful stay! The pool and hot tub are amazing. The staff is so accommodating. They even got a shower chair for my mom. The breakfast is delicious. Beds are so comfortable."
Reviewed on Sep 20, 2026
Best Western Plus Executive Residency Jackson Northeast
2443 CHRISTMASVILLE COVE Jackson TN
Fully refundableReserve now, pay when you stay
$91 nightly
$105 total
Oct 4 - Oct 5
Total with taxes and fees
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
Chickasaw State Park
8.2/10 (41 reviews)
You can take time to visit Chickasaw State Park during your travels to Henderson. While you're in the area, wander around the parks.
Chickasaw Golf Course
7.0/10 (7 reviews)
Enjoy a round of golf in Henderson at Chickasaw Golf Course. While you're in the area, wander around the parks.
Black Box Theatre
You can get tickets for a performance at Black Box Theatre during your stay in Henderson. While you're in the area, wander around the parks.
Henderson Wi-Fi Park
After visiting Henderson Wi-Fi Park, make a plan to see the other sights and activities in Henderson. While you're in the area, wander around the parks.
Chester County Library
After visiting Chester County Library, make a plan to see the other sights and activities in Henderson. While you're in the area, wander around the parks.
Henderson City Hall
After visiting Henderson City Hall, make a plan to see the other sights and activities in Henderson. While you're in the area, wander around the parks.
Roadside Park
After visiting Roadside Park, make a plan to see the other sights and activities in Henderson. While you're in the area, wander around the parks.
Dixie Youth Park
Explore the great outdoors at Dixie Youth Park, a lovely green space in Henderson. While you're in the area, wander around the parks.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
