Chester Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

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

Find the Best Chester Vacation Packages

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
The price is ￥13,657 per night from Aug 11 to Aug 12
￥13,657
￥16,149 total
Aug 11 - Aug 12
includes taxes & fees
9.4/10 Exceptional! (225 reviews)
"Great hotel, room was nice and clean."

Reviewed on Jul 30, 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
The price is ￥9,156 per night from Aug 23 to Aug 24
￥9,156
￥11,202 total
Aug 23 - Aug 24
includes taxes & fees
6/10 (23 reviews)
"It was fair all the way around"

Reviewed on Aug 2, 2025

Crossroads Motel Seiling Us 60
Just Dune It - West

Just Dune It - West

Waynoka
10/10 Exceptional! (41 reviews)
Home away from home
"Always very pleasant and family environment. Close to dunes and very accommodating facility. Very popular place when available. It’s always our first pick. Thanks Rocky."

Reviewed on Jul 7, 2025

Get rates
Just Dune It - West
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.

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this popular destination 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?
January, February and March are great times to search for cheap Chester vacation packages. Opting to travel in quieter periods means you can usually find lower prices on flights and hotels.
How many days is enough for Chester?
Generally, a handful of days is enough to explore the top attractions during your Chester vacation. However, if you prefer to have time to chill out or take day tours, consider extending your trip.
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.
How to plan a trip to Chester?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit Chester.
  2. Budget wisely: In addition to the cost of your accommodations, you should factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Chester.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Chester. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Combine your airfare and accommodations: Once you've nailed down your travel dates and duration, book the ideal Chester vacation package for you.

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