Chester Vacations from $298

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

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

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Crossroads Motel Seiling Us 60

Crossroads Motel Seiling Us 60

2.5 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Enid (WDG)
6.2/10 (20 reviews)
The manager's assistance made the check-in process very comfortable, and the online option saved me considerable time. Everything else went smoothly, and the customer service was excellent. The rooms were also clean.

Reviewed on Jun 11, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chester
View all trips

Chester Hotel Deals

Best Western Plus Fairview Inn & Suites
Best Western Plus Fairview Inn & Suites
2.5 out of 5
802 N Main St, Fairview, OK
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $110 total per night from Aug 3 to Aug 4
$110 total
Aug 3 - Aug 4
Total includes taxes and fees
9.4/10 Exceptional! (221 reviews)
"Was clean and comfortable"

Reviewed on Jul 8, 2025

Best Western Plus Fairview Inn & Suites
Crossroads Motel Seiling Us 60
Crossroads Motel Seiling Us 60
2.5 out of 5
805 NE US Hwy 60, Seiling, OK
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $65 total per night from Aug 3 to Aug 4
$65 total
Aug 3 - Aug 4
Total includes taxes and fees
6.2/10 (20 reviews)
"The manager's assistance made the check-in process very comfortable, and the online option saved me considerable time. Everything else went smoothly, and the customer service was excellent. The rooms were also clean."

Reviewed on Jun 11, 2025

Crossroads Motel Seiling Us 60
Escape to Waynoka: Your Ultimate 4-Bedroom Retreat Near Little Sahara State Park
Escape to Waynoka: Your Ultimate 4-Bedroom Retreat Near Little Sahara State Park
Waynoka
10/10 Exceptional! (4 reviews)
Excellent location in town and close to the dunes.
"Easy access to the dunes and still close to town."

Reviewed on May 24, 2025

Get rates
Escape to Waynoka: Your Ultimate 4-Bedroom Retreat Near Little Sahara State Park
See all 40 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

More vacations you might like

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this popular destination from $298 on Expedia. But how much your vacation to Chester costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Chester?
You can typically find reduced prices and greater availability in January, June and November. Browse our cheap Chester vacation packages and you could get some excellent off-season deals.
How many days is enough for Chester?
With a well-planned itinerary, you can easily tick off the main Chester attractions in a handful of days. But if you'd like to discover lesser-known spots or go on day tours, think about 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 destination and travel dates under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can customize 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 get 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 land you great savings when compared to booking flights and stays individually. Better still, you can customize your Chester trip to match your exact style. Choose 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?
If you've got your Chester vacation dates locked in, book as soon as you can to bag some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for quick escapes.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Secure your dream trip to Chester with our Book Now, Pay Later vacations. No need to scrimp and save or wait for the next payday --- we've joined forces with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stick to your budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.