Chester Holidays

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Top hotels in Chester

Beard and Lady Inn

Beard and Lady Inn

3 out of 5
411 E Front Ave Chester AR
The price is S$142 per night from 14 Jul to 15 Jul
S$142
14 Jul - 15 Jul
includes taxes & fees
9.2/10 Wonderful! (49 reviews)
"I read previous reviews that talked about noises, creaking of the wood floors, and how you can hear everything through the walls. Please keep in mind this is an AUTHENTIC 1800'S HOTEL. The owners have definitely did a very good job at preserving that authenticity. I stayed in room 4, the children's ..."

Reviewed on 28 Jun, 2026

Beard and Lady Inn
Cherokee Casino & Hotel Roland

Cherokee Casino & Hotel Roland

3.5 out of 5
109 Cherokee Boulevard Roland OK
The price is S$136 per night from 14 Jul to 15 Jul
S$136
14 Jul - 15 Jul
includes taxes & fees
9.2/10 Wonderful! (1,024 reviews)
"Clean. Staff was friendly and helpful."

Reviewed on 11 Jul, 2026

Cherokee Casino & Hotel Roland
La Quinta Inn & Suites by Wyndham Fort Smith

La Quinta Inn & Suites by Wyndham Fort Smith

3 out of 5
6700 S Boston Street Fort Smith AR
Fully refundableReserve now, pay when you stay
The price is S$109 per night from 14 Jul to 15 Jul
S$109
14 Jul - 15 Jul
includes taxes & fees
8.4/10 Very good! (1,016 reviews)
"Everything was great except for the swimming pool. It was not open due to repairs needing to be made."

Reviewed on 11 Jul, 2026

La Quinta Inn & Suites by Wyndham Fort Smith
See all 227 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.

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. 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.