Chester Vacations from $345

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Black Angus Motel Poteau
Homewood Suites by Hilton Fort Smith
Cherokee Casino & Hotel Roland
Home2 Suites by Hilton Fort Smith AR
Hampton Inn Van Buren
Don't see what you're looking for?
See all available trips from Columbus to Chester
View all trips

Chester Hotel Deals

Beard and Lady Inn

Beard and Lady Inn

3 out of 5
411 E Front Ave, Chester, AR
$96 nightly
The price is $106 total per night from Dec 4 to Dec 5
$106 total
Dec 4 - Dec 5
Total with taxes and fees
9.2/10 Wonderful! (34 reviews)
Quiet and secluded with no TVs. All amenities needed were available. Comfortable beds and loved the theme of the place.

Reviewed on Nov 3, 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
$195 nightly
The price is $214 total per night from Nov 20 to Nov 21
$214 total
Nov 20 - Nov 21
Total with taxes and fees
9.8/10 Exceptional! (27 reviews)
Clean very clean!! Had everything we needed for our stay. Quiet and relaxing. The host was very responsive to all questions. Ohh yes then ther is the view. Just to sit there and see a small part of God's creation.

Reviewed on Nov 4, 2025

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
9.2/10 Wonderful! (34 reviews)
Very clean on a nice quiet road. All the amenities you need.

Reviewed on Oct 14, 2025

Old Cross Roads Cabin 3 bed/2 bath
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

More vacations you might like

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from $345 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.