Chester Vacations from $803

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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.
The Parker Lodge

The Parker Lodge

2 out of 5
Price was $859, price is now $803 per person
$803
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Eugene (EUG) to Fort Smith (FSM)
7/10 Good! (414 reviews)
Ok

Reviewed on Jul 6, 2026

Wyndham Fort Smith City Center

Wyndham Fort Smith City Center

4 out of 5
Price was $1,047, price is now $937 per person
$937
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Eugene (EUG) to Fort Smith (FSM)
8.2/10 Very Good! (1,004 reviews)
Loved it and the stuff were so kind and welcoming

Reviewed on Jul 8, 2026

SureStay Plus Hotel By Best Western Poteau

SureStay Plus Hotel By Best Western Poteau

2.5 out of 5
Price was $930, price is now $847 per person
$847
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Eugene (EUG) to Fort Smith (FSM)
8.6/10 Excellent! (558 reviews)
Nice and quite. Clean room. Spacious room. Good breakfast every morning. Close to places to see and things to do. Friendly staff. No problems.

Reviewed on Jul 7, 2026

Best Western Van Buren Inn

Best Western Van Buren Inn

2.5 out of 5
Price was $978, price is now $899 per person
$899
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Eugene (EUG) to Fort Smith (FSM)
8.4/10 Very Good! (800 reviews)
Staff was awesome and there was a good breakfast in the morning.

Reviewed on Jul 8, 2026

La Quinta Inn & Suites by Wyndham Fort Smith

La Quinta Inn & Suites by Wyndham Fort Smith

3 out of 5
Price was $928, price is now $860 per person
$860
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Eugene (EUG) to Fort Smith (FSM)
8.4/10 Very Good! (1,007 reviews)
Very clean and nice staff. Very much appreciated....

Reviewed on Jul 8, 2026

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Chester Hotel Deals

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
$216 nightly
The price is $239 total per night from Jul 20 to Jul 21
$239 total
Jul 20 - Jul 21
Total with taxes and fees
10/10 Exceptional! (48 reviews)
"Sunset views are breathtaking and cabin was really clean and really nice."

Reviewed on Jul 6, 2026

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

Beard and Lady Inn

3 out of 5
411 E Front Ave Chester AR
$105 nightly
The price is $116 total per night from Jul 12 to Jul 13
$116 total
Jul 12 - Jul 13
Total with taxes and fees
9.2/10 Wonderful! (49 reviews)
"I read previous reviews that talked about noises, creaking of the wood floors, and how you can hear everything through the walls. Please keep in mind this is an AUTHENTIC 1800'S HOTEL. The owners have definitely did a very good job at preserving that authenticity. I stayed in room 4, the children's ..."

Reviewed on Jun 28, 2026

Beard and Lady Inn
Cherokee Casino & Hotel Roland

Cherokee Casino & Hotel Roland

3.5 out of 5
109 Cherokee Boulevard Roland OK
$99 nightly
The price is $105 total per night from Jul 14 to Jul 15
$105 total
Jul 14 - Jul 15
Total with taxes and fees
9.2/10 Wonderful! (1,022 reviews)
"Front office ladies were so nice! Loved the room."

Reviewed on Jul 8, 2026

Cherokee Casino & Hotel Roland
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 from $803 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.