Chester Vacations from $426
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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.
The Latest Chester vacation packages
Price found within the past 48 hours. Click for updated prices.
Beard and Lady Inn
$426
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Fort Smith (FSM)
9.2/10 Wonderful! (52 reviews)
We would love to come back! Loved the soaking claw-foot tub and b&w decor in our room. A few minor things: When we booked via hotels.com it mentioned a welcome gift with the room we chose (#11) but there wasn't anything. It also felt a bit like the place was left to its own devices... breakfast list mentioned yogurt, but there was none. However, there was oatmeal and coffee. The place was so quiet and clean. We met Eve (not the owner) who has the Apothecary next door and she was lovely! We were the only ones renting the night we stayed so we had the entire place to ourselves. Be prepared that there is nothing around. I mean NOTHING. So you'll have to take a short drive in to eat dinner etc., which was fine with us. Overall, a very unique place to stay! It felt like taking a trip back to the 1800s and LOVED not having any TV in sight! Sad to know it's up for sale... I hope the new owners will keep it as is.
Reviewed on Aug 24, 2026
Chester Hotel Deals
Beautiful modern cabin on top of the mountain with stunning sunset views.
Chester AR
$259 nightly
$287 total
Sep 8 - Sep 9
Total with taxes and fees
10/10 Exceptional! (51 reviews)
"Great experience. My wife and I are both teachers, and wanted a little get away where we could have plenty of quiet and beautiful nature. The property itself is very cool! But the view is so peaceful and serene, it’s just what we had hoped for. And no one near us, just the sounds of nature and that ..."
Reviewed on Aug 16, 2026
Beard and Lady Inn
411 E Front Ave Chester AR
$90 nightly
$99 total
Aug 30 - Aug 31
Total with taxes and fees
9.2/10 Wonderful! (55 reviews)
"We would love to come back! Loved the soaking claw-foot tub and b&w decor in our room. A few minor things: When we booked via hotels.com it mentioned a welcome gift with the room we chose (#11) but there wasn't anything. It also felt a bit like the place was left to its own devices... breakfast list ..."
Reviewed on Aug 24, 2026
Cherokee Casino & Hotel Roland
109 Cherokee Boulevard Roland OK
$119 nightly
$126 total
Aug 26 - Aug 27
Total with taxes and fees
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 from $426 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.
