Chester County Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Our pick of the best Chester County Hotel Deals

Americana Inn

Americana Inn

2.5 out of 5
550 Sanford St, Henderson, TN
The price is NZ$137 per night from 18 Aug to 19 Aug
NZ$137
18 Aug - 19 Aug
includes taxes & fees
7.6/10 Good! (310 reviews)
Not too bad.
"The Overall stay was very good. The only negitive was actually a big one. The continental breakfast was very weak.....at best. I think more could have been provided."

Reviewed on 26 Jul. 2025

Americana Inn
Best Western Plus Executive Residency Jackson Northeast

Best Western Plus Executive Residency Jackson Northeast

3 out of 5
2443 CHRISTMASVILLE COVE, Jackson, TN
Fully refundableReserve now, pay when you stay
The price is NZ$197 per night from 17 Aug to 18 Aug
NZ$197
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Check in was very slow, and other than the dirty swimming pool, everything was very clean and the staff was very friendly and helpful. Breakfast was great, but they were out of coffee and the staff wasn't in a hurry to restock, but the food was stocked and great. Rooms very clean and the beds comfortable, ..."

Reviewed on 8 Aug. 2025

Best Western Plus Executive Residency Jackson Northeast
Fairfield Inn & Suites by Marriott Jackson

Fairfield Inn & Suites by Marriott Jackson

2.5 out of 5
1335 Vann Dr, Jackson, TN
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 23 Aug to 24 Aug
NZ$202
23 Aug - 24 Aug
includes taxes & fees
9/10 Wonderful! (780 reviews)
"ok"

Reviewed on 4 Aug. 2025

Fairfield Inn & Suites by Marriott Jackson
See all 190 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.

Frequently asked questions

How much does a Chester County holiday package cost?
Handcraft your Chester County holiday package from only . Choose from any combination of flights, hotels and rental cars to craft the trip of your dreams. Remember to add on some activities and experiences!
How do I get a cheap travel package to Chester County?
Bundle your hotels and flights with Expedia to save big on your next trip. With over 550 air carriers and 1 000 000 hotel options throughout the world, your Chester County holiday package can be tailored exactly to suit your travel style. With all that extra money, why not include one or two interesting tours and experiences? It's an easy way to unlock even more bargains. The holiday you've always dreamed of in Chester County is much closer than you thought!
What are the top hotels in Chester County?
If you're on your way to Henderson, you can't go past Americana Inn and The Inn At Pearce Point - - A Peaceful Farm Retreat Conveniently To Henderson. Both are excellent bases for discovering this exciting Chester County city.
How far in advance should I book my Chester County holiday?
While not all air carriers advertise tickets early, you can normally start comparing international flights on Expedia up to 12 months in advance. This is the time you'll score some fantastic deals. If you're purchasing tickets last minute, you might get lucky. Sometimes the cheapest prices emerge just weeks prior to departure.
What does an Expedia Chester County travel package include?
With Expedia, you can select a combination of hotels, flights and car rentals to build your ideal Chester County travel package. Once you've made your booking, you can add on the fun things like sightseeing tours and activities. Don't forget — the more you bundle, the more cash you'll save!
What should I know before booking a Chester County travel package?
A travel package can be easier on the credit card than individually booking everything you need for your adventure. For example, bundle your flights, hotels and rental cars and land a great deal. Whatever sort of holiday you're planning, you'll find a package that's right for you.
Can I choose my airline with a Chester County Expedia holiday package?
Most definitely. Expedia has more than 550 airline partners to pick from globally. With such a big range of choice, finding the ideal carrier to fly you to Chester County will be a cinch.
If I'm not able to travel, can I cancel my Chester County holiday package?
Don't worry if you're rethinking your Chester County holiday package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We totally get that life can sometimes throw you a curveball, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we're here to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.