Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

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 2.603.304 ₫ per night from 4 Aug to 5 Aug
2.603.304 ₫
2.883.159 ₫ total
4 Aug - 5 Aug
includes taxes & fees
9.2/10 Wonderful! (51 reviews)
"This was a short overnight after a concert in Fayetteville. We love the Beard & Lady! It is such a neat property. Our room was very comfortable and they were SO accommodating in letting us check in early to drop off our luggage on the way to the concert. The concert was rain delayed so it was well ..."

Reviewed on 20 Jul 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 2.082.644 ₫ per night from 4 Aug to 5 Aug
2.082.644 ₫
2.207.602 ₫ total
4 Aug - 5 Aug
includes taxes & fees
Cherokee Casino & Hotel Roland
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 2.346.918 ₫ per night from 2 Sept to 3 Sept
2.346.918 ₫
2.687.222 ₫ total
2 Sept - 3 Sept
includes taxes & fees
Wyndham Fort Smith City Center
See all 224 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.