Chester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

Americas Best Value Inn Belleville

Americas Best Value Inn Belleville

2 out of 5
1616 U.S. Hwy 36 Belleville KS
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Jul 3 to Jul 4
CA $110
CA $125 total
Jul 3 - Jul 4
includes taxes & fees
7.4/10 Good! (330 reviews)
"Roaches everywhere"

Reviewed on Jun 29, 2026

Americas Best Value Inn Belleville
RIVERSIDE MOTEL

RIVERSIDE MOTEL

2 out of 5
305 S 13th St Hebron NE
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Jul 8 to Jul 9
CA $153
CA $170 total
Jul 8 - Jul 9
includes taxes & fees
9/10 Wonderful! (107 reviews)
"Beautiful clean room.,"

Reviewed on Jun 28, 2026

RIVERSIDE MOTEL
Super 8 by Wyndham Belleville

Super 8 by Wyndham Belleville

2 out of 5
1410 28th St Belleville KS
Fully refundableReserve now, pay when you stay
The price is CA $89 per night from Jul 15 to Jul 16
CA $89
CA $106 total
Jul 15 - Jul 16
includes taxes & fees
7/10 Good! (262 reviews)
"We had a clean room, and everything worked well! We will stay there again I’m sure! Thanks"

Reviewed on Jun 29, 2026

Super 8 by Wyndham Belleville
See all 17 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Chester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chester?
January, February and July are the best times to search for cheap Chester vacation packages. Choosing to travel in quieter months means you'll typically find lower prices on hotels and flights.
How many days is enough for Chester?
With a well-organized itinerary, you can easily visit the top Chester sights in a few days. But if you prefer to discover hidden spots or go on day trips, consider booking your Chester vacation for longer.
How to find the best Chester package deals?
Begin your search for a Chester package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Chester package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chester adventure underway.
Is it cheaper to book a Chester vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Chester vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Chester?
Land incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chester escape.
How to plan a trip to Chester?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Chester.
  2. Set your budget: Consider expenses like transportation, flights and meals when calculating how much to set aside for your trip to Chester. Then, choose a hotel that suits your budget, whether that's a wallet-friendly option or a deluxe retreat.
  3. Decide how long to go for: Now that you know more about Chester, you can figure out the ideal length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Chester vacation package.

Explore a world of travel with Expedia

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