Chester Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.

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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
The price is CA $140 per night from Jul 20 to Jul 21
CA $140
CA $335 total
Jul 20 - Jul 21
includes taxes & 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
The price is CA $140 per night from Jul 12 to Jul 13
CA $140
CA $155 total
Jul 12 - Jul 13
includes taxes & 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
The price is CA $140 per night from Jul 15 to Jul 16
CA $140
CA $149 total
Jul 15 - Jul 16
includes taxes & fees
9.2/10 Wonderful! (1,023 reviews)
"The room was large, clean, and the bathroom was large. My only complaint was the in room coffee was very good and the food was below par. We were not there on a weekend and the buffet wasn’t available."

Reviewed on Jul 9, 2026

Cherokee Casino & Hotel Roland
See all 228 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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Chester vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Chester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chester?
The off-season is the best time to head to Chester if you're on a budget. Another tip for finding cheap Chester vacation packages? Avoid visiting during public holidays and any major festivals.
How many days is enough for Chester?
With a well-organized travel plan, you can easily visit the top Chester attractions in a few days. But if you'd like to explore off the beaten track or take day trips, think about booking your Chester vacation for longer.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chester vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Chester vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Chester?
Enjoy incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Chester getaway.
How to plan a trip to Chester?

  1. Choose your travel dates: The things you want to do in Chester and your favourite season can help you decide when to go.
  2. Set your budget: Factor in expenses like food, flights and transportation when calculating how much to put aside for your trip to Chester. Then, choose a hotel that works with your budget, whether that's an affordable stay or a deluxe getaway.
  3. Decide how long to go away for: Now that you know more about Chester, you can figure out the right length of your break. Put together a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Chester vacation package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.