Chester Vacations

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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.

Chester Hotel Deals

Beard and Lady Inn

Beard and Lady Inn

3 out of 5
411 E Front Ave Chester AR
$105 nightly
The price is $115 total per night from Apr 8 to Apr 9
$115 total
Apr 8 - Apr 9
Total with taxes and fees
9.4/10 Exceptional! (39 reviews)
The Beard and Lady Inn was a very interesting place to stay. It was a nice change from the usual hotels. It had everything I needed for my stay.

Reviewed on Mar 22, 2026

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
$197 nightly
The price is $217 total per night from Apr 13 to Apr 14
$217 total
Apr 13 - Apr 14
Total with taxes and fees
9.8/10 Exceptional! (36 reviews)
Stay was amazing. View was beautiful and far enough from town to enjoy the quiet and view but close enough that it wasn't hard to get anywhere. Host was accommodating. We weren't able to enjoy the grill due to it not having any fuel.

Reviewed on Jan 14, 2026

Beautiful modern cabin on top of the mountain with stunning sunset views.
Old Cross Roads Cabin 3 bed/2 bath

Old Cross Roads Cabin 3 bed/2 bath

Chester AR
9.4/10 Exceptional! (36 reviews)
Our hosts were very welcoming and even allowed us to check in a day early when our plans had to be changed at the last minute. They also were helpful when we encountered a couple of difficulties during our stay.

Reviewed on Nov 10, 2025

Get rates
Old Cross Roads Cabin 3 bed/2 bath
See all 226 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.