Chester Trips (flight + hotel)

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Top hotels in Chester

Americas Best Value Inn & Suites Spring Valley
Americas Best Value Inn & Suites Spring Valley
2 out of 5
745 N Broadway St, Spring Valley, MN
Fully refundableReserve now, pay when you stay
The price is P5,027 per night from Jul 14 to Jul 15
P5,027
P5,549 total
Jul 14 - Jul 15
includes taxes & fees
8/10 Very Good! (397 reviews)
Nice stay in a small town
"It was a nice hotel for a small town. The family that runs it were polite and very helpful."

Reviewed on Jul 2, 2025

Americas Best Value Inn & Suites Spring Valley
AmericInn by Wyndham Osage
AmericInn by Wyndham Osage
2.5 out of 5
2212 Highway 218, Osage, IA
Fully refundableReserve now, pay when you stay
The price is P5,906 per night from Aug 10 to Aug 11
P5,906
P6,614 total
Aug 10 - Aug 11
includes taxes & fees
9.4/10 Exceptional! (251 reviews)
"Comfortable"

Reviewed on Jun 30, 2025

AmericInn by Wyndham Osage
Western Inn & Suites
Western Inn & Suites
2 out of 5
1530 Main St,, Osage, IA
Fully refundableReserve now, pay when you stay
The price is P3,558 per night from Jul 15 to Jul 16
P3,558
P3,985 total
Jul 15 - Jul 16
includes taxes & fees
6.4/10 (23 reviews)
"Bed clunked everytime I moved"

Reviewed on Jun 22, 2025

Western Inn & Suites
See all 27 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 pleasantly surprised at how much a vacation to Chester costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chester?
If you're looking to score a cheap Chester vacation package, consider visiting in January, February and November. You'll generally find lower rates on hotels and airfares during these quieter months --- ideal for budget-conscious travelers.
How many days is enough for Chester?
With a well-planned schedule, you can easily hit the top Chester sights in a handful of days. But if you'd like to venture off the beaten track or go on day tours, think about booking your Chester vacation for longer.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Chester package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your next Chester getaway by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Chester?
Score incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Chester break.
How to plan a trip to Chester?

  1. Choose when to go: Check your calendar and pack your bags. Your favorite time of year and the activities on offer will also help you decide when to vacation in Chester.
  2. Set a budget: Consider expenses such as transportation, flights and meals when calculating how much to set aside for your trip to Chester. Then, choose a hotel that fits your budget, whether that's a wallet-friendly option or a more upscale retreat.
  3. Decide how long to go away for: Now that you're up to speed on Chester, you can work out the ideal length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Chester vacation package that brings all your bookings together.

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