Chester Holidays

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    Better together
    Save up to S$134 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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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Chester

Wyndham Fort Smith City Center
Wyndham Fort Smith City Center
4 out of 5
700 Rogers Ave, Fort Smith, AR
Fully refundableReserve now, pay when you stay
The price is S$129 per night from 3 Jul to 4 Jul
S$129
3 Jul - 4 Jul
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Good hotel, only issue I really had was the ac in the room was off and it was 90 inside the room. Took to almost 11 to cool off for me to fall a sleep"

Reviewed on 22 Jun, 2025

Wyndham Fort Smith City Center
Courtyard Marriott Fort Smith Downtown
Courtyard Marriott Fort Smith Downtown
3 out of 5
900 Rogers Ave, Fort Smith, AR
Fully refundableReserve now, pay when you stay
The price is S$129 per night from 20 Jul to 21 Jul
S$129
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"It was a nice example of the class of hotel it is,"

Reviewed on 24 Jun, 2025

Courtyard Marriott Fort Smith Downtown
Cherokee Casino & Hotel Roland
Cherokee Casino & Hotel Roland
3.5 out of 5
109 Cherokee Boulevard, Roland, OK
9.2/10 Wonderful! (1,002 reviews)
"Very nice and clean rooms."

Reviewed on 25 Jun, 2025

Get rates
Cherokee Casino & Hotel Roland
See all 214 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'll find cheap prices on Expedia for your Chester getaway. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Chester costs.
What are the cheapest months to go to Chester?
The off-season is the best time to travel to Chester if you're trying to keep costs down. Another tip for getting cheap Chester holiday packages? Try to avoid public holidays and any major events.
How many days is enough for Chester?
The ideal length of your Chester holiday depends on what you'd like to do and see. Typically, a handful of days to a week will give you enough time to visit all the main attractions and discover some hidden spots along the way.
How to find the best Chester package deals?
Landing a cheap Chester package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most affordable Chester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Chester holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation individually. Better still, you can customise your Chester trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Chester?
Land incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Chester escape.
How to plan a trip to Chester?

  1. Pick your dates: What you want to do in Chester and your preferred season can help you decide when to go.
  2. Budget wisely: Besides the cost of your accommodation, you'll need to consider other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that may arise during your trip to Chester.
  3. Decide how many days away: Start by listing all the attractions and activities you'd like to experience in Chester. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalised Chester holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.