Chester Vacations

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Find the Best Chester Vacation Packages

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
Fully refundable
The price is AEDĀ 356 per night from Nov 12 to Nov 13
AEDĀ 356
AEDĀ 822 total
12 Nov - 13 Nov
includes taxes & fees
10/10 Exceptional! (54 reviews)
"N/A"

Reviewed on 18 October 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 AEDĀ 332 per night from Nov 24 to Nov 25
AEDĀ 332
AEDĀ 368 total
24 Nov - 25 Nov
includes taxes & fees
9.4/10 Exceptional! (69 reviews)
"This place was absolutely AMAZING!!! A haunted GEM!! Perfect peace and quiet!! NO TVs was the BEST!! So clean!! Beds very comfy.."

Reviewed on 9 November 2026

Beard and Lady Inn
Old Cross Roads Cabin 3 bed/2 bath

Old Cross Roads Cabin 3 bed/2 bath

Chester AR
9.4/10 Exceptional! (37 reviews)
"Nice place and convenient to atv trails"

Reviewed on 2 November 2026

Get rates
Old Cross Roads Cabin 3 bed/2 bath
See all 250 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.

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 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," "Traveler 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 favorite 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 favorite 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.