Chester Vacations

Book a Hotel + Flight or Car together to unlock savings

Your Chester Vacation

Skip the hassle of organizing your next great adventure with a Chester vacation package. Whether you're interested in its food, history, art or something else, this city offers endless possibilities for fun. A trip to Chester is an ideal opportunity to take in the sights. Be sure to look around renowned attractions like Lake Fort Smith State Park, Artist Point and Evans Trail Loop. Whoever you're heading away with and whatever you want to spend, your ultimate Chester vacation is just clicks away with Expedia.

Chester Hotel Deals

Beard and Lady Inn

Beard and Lady Inn

3 out of 5
411 E Front Ave Chester AR
$97 nightly
The price is $107 total per night from Feb 9 to Feb 10
$107 total
Feb 9 - Feb 10
Total with taxes and fees
9.4/10 Exceptional! (35 reviews)
Everything, very unique and exciting experience. Already looking to book again.

Reviewed on Nov 10, 2025

Beard and Lady Inn
Beautiful modern cabin on top of the mountain with stunning sunset views.

Beautiful modern cabin on top of the mountain with stunning sunset views.

Chester AR
$193 nightly
The price is $212 total per night from Jan 20 to Jan 21
$212 total
Jan 20 - Jan 21
Total with taxes and fees
9.8/10 Exceptional! (35 reviews)
We had a good stay. Clean and peaceful.

Reviewed on Dec 28, 2025

Beautiful modern cabin on top of the mountain with stunning sunset views.
Cherokee Casino & Hotel Roland

Cherokee Casino & Hotel Roland

3.5 out of 5
109 Cherokee Boulevard Roland OK
$88 nightly
The price is $93 total per night from Jan 15 to Jan 16
$93 total
Jan 15 - Jan 16
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
room was nice and clean. bed was comfortable. staff was friendly

Reviewed on Jan 12, 2026

Cherokee Casino & Hotel Roland
See all 229 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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Fort Smith Regional Airport (FSM)
Population
160
Top Sights
Lake Fort Smith State Park, Evans Trail Loop and Artist Point

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Frequently asked questions

How much does a Chester vacation 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 vacation to Chester costs.
What are the cheapest months to go to Chester?
You can generally find lower rates and greater availability in November, December and January. Explore our cheap Chester vacation packages and you could land some great off-season deals.
How many days is enough for Chester?
With a well-organized itinerary, you can easily visit the top Chester attractions in a few days. But if you prefer to discover hidden gems or take day trips, consider booking your Chester vacation for longer.
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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations individually. Better still, you can customize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Chester vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.