Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by A Jaunt With Joy

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NZ$616 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Chester Holiday

Our pick of the best Chester Hotel Deals

Motel 6 Richburg, SC

Motel 6 Richburg, SC

2 out of 5
2912 Parkway Blvd, Chester, SC
Fully refundableReserve now, pay when you stay
The price is NZ$137 per night from 25 Aug to 26 Aug
NZ$137
25 Aug - 26 Aug
includes taxes & fees
6.6/10 (322 reviews)
"The breakfast was gross and we had to change rooms to an upstairs one because the toilet was broken in the first one."

Reviewed on 20 Aug. 2025

Motel 6 Richburg, SC
Inn Upon Moon River Plantation

Inn Upon Moon River Plantation

2.5 out of 5
119 Pinckney Street, Chester, SC
The price is NZ$264 per night from 26 Aug to 27 Aug
NZ$264
26 Aug - 27 Aug
includes taxes & fees
9/10 Wonderful! (44 reviews)
Southern Charm & Hospitality
"I thoroughly enjoyed my stay! The House is beautiful and filled with memorabilia of great artists from the jazz and blues fields. The area is very quiet and picturesque. I look forward to my next trip up to the Chester, SC area. I highly recommend this Bed and Breakfast!"

Reviewed on 24 Jul. 2025

Inn Upon Moon River Plantation
Clarion Pointe Near University

Clarion Pointe Near University

2.5 out of 5
1106 N. Anderson Road, Rock Hill, SC
Fully refundableReserve now, pay when you stay
The price is NZ$133 per night from 31 Aug to 1 Sept
NZ$133
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Very convenient location just off I77."

Reviewed on 20 Aug. 2025

Clarion Pointe Near University
See all 246 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.

Frequently asked questions

How much does a Chester holiday package cost?
You can grab a holiday package to this destination on Expedia. However, how much your holiday to Chester costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Chester?
September, October and December are great times to search for cheap Chester holiday packages. Travelling in less busy months means you can usually find better prices on accommodation and flights.
How many days is enough for Chester?
Usually, a handful of days is enough to explore the main attractions during your Chester holiday. But if you want to have time to unwind or go on day tours, consider extending your trip.
Is it worth booking a holiday package to Chester?
Chester has everything you need for an unforgettable trip. Begin your Chester holiday on a high note by checking out major attractions like Chester State Park.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Chester holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have the freedom to create a personalised Chester holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Chester?
Enjoy incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Chester trip.
How to plan a trip to Chester?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Chester.
  2. Set your budget: Factor in costs such as food, flights and transportation when working out how much to set aside for your trip to Chester. Then, pick a property that matches your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Decide how long to go away for: Now that you're more familiar with Chester, you can figure out the ideal length of your holiday. Put together a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chester holiday package that brings all your bookings together.

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