Chester County Holidays

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Your Chester County Holiday

Make planning your next getaway easy with a Chester County holiday package. Whether it's the history, cuisine or something else entirely that lures you to this destination, our package deals will help you discover it all. A trip to Chester County wouldn't be complete without getting to some of its most well-known cities, starting with Henderson. Some of the top attractions here include Chickasaw State Park and Chickasaw Golf Course. Silerton is another favourite city with Chester County travellers. Visitors to this exciting destination enjoy Chickasaw State Park and Chickasaw Golf Course. If you're ready to stop daydreaming and start doing, Expedia will help turn your Chester County holiday into reality.

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

Our pick of the best Chester County Hotel Deals

Americana Inn
Americana Inn
2.5 out of 5
550 Sanford St, Henderson, TN
Stay at this business-friendly motel in Henderson. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (298 reviews)
"A quaint little hotel under new management. They are doing a lot of renovations to improve the property. They already have it VERY clean and running smoothly. Given time to finish their updates, I can see that this will be a great place to stay while in town."

Reviewed on 18 Jun 2025

Americana Inn
Fairfield Inn & Suites by Marriott Jackson
Fairfield Inn & Suites by Marriott Jackson
2.5 out of 5
1335 Vann Dr, Jackson, TN
Stay at this business-friendly hotel in Jackson. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (749 reviews)
"Friendly staff. Convenient location. Very clean."

Reviewed on 23 Jun 2025

Fairfield Inn & Suites by Marriott Jackson
SpringHill Suites by Marriott Jackson
SpringHill Suites by Marriott Jackson
2.5 out of 5
2407 CHRISTMASVILLE COVE, Jackson, TN
Stay at this business-friendly hotel in Jackson. Enjoy free breakfast, free parking and an outdoor pool. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (617 reviews)
Great Stay
"Nice size room, comfortable beds, great lighting in the bathroom, yummy breakfast!"

Reviewed on 17 Jun 2025

SpringHill Suites by Marriott Jackson
See all 170 properties in Chester County
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Chester County travel package cost?
Create unforgettable memories with our Chester County travel packages, which start from only . Select the hotels and flights that suit your style. Then, add on one or two tours or activities for a memorable getaway.
If I'm not able to travel, can I cancel my Chester County travel package?
Whether it's your hotel, flight or rental car, yes, you can amend or cancel it. Locked in your Chester County travel package in the last 24 hours? You may be able to make changes at no cost. For bookings older than that, you may be charged a fee by your airline, hotel or car rental company. For more information, check out our Customer Service Portal. We're here to help you each step of the way.
How do I get a cheap travel package to Chester County?
If you love amazing deals, bundle your bookings into a Chester County travel package. Whether you're searching for flights, hotels, day tours or rental cars, you can book everything in one place. You'll have plenty of choice at your fingertips as well. Expedia has over 550 air carriers and 1,000,000 hotels across the globe to select from. Fly with who you want, book a room where you like and save precious dollars --- now that's the perfect escape!
Does Expedia offer Book Now, Pay Later Chester County holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has worked out a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a terrific getaway without using up all your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Check out these flexible payment options:
  • Pay monthly holidays: Klarna offers easy monthly payment plans that suit all types of budgets, so you can take that well-deserved holiday sooner.
  • Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you stumble on an incredible deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock it in.

What are the top hotels in Chester County?
Americana Inn and The Inn At Pearce Point - - A Peaceful Farm Retreat Conveniently To Henderson are two popular places to stay in Henderson. A must-do on any good Chester County itinerary, we recommend taking the time to fully discover this happening city.
How far in advance should I book my Chester County holiday?
To land rock-bottom prices, book nice and early. Airlines generally release flight tickets, along with some of the lowest fares, around a year prior to departure. Hotels, car rental and activities should also be booked early so you can have the pick of the bunch. If you're in need of a last-minute getaway in Chester County, there are always plenty of great bargains to be had on Expedia. Book something in today!
What does an Expedia Chester County travel package include?
That depends entirely on you. You can select from a range of Chester County packages, such as a hotel, rental car and flight. You can also book a hotel with a flight, or a rental car and a flight. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your Chester County break looks like, you're sure to save!
What should I know before booking a Chester County travel package?
Our prices are already low. However, you'll score even better deals when you book your flights, hotels and car rentals together. With an Expedia package, you'll always get transparent pricing and loads of choice.
Can I choose my airline with a Chester County Expedia travel package?
Yes, and with more than 550 airlines to choose from globally, you have loads of choice. Look through the available options and find out which airline suits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.