Chester Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Chester

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 S$147 per night from 29 Jun to 30 Jun
S$147
29 Jun - 30 Jun
includes taxes & fees
9.4/10 Exceptional! (242 reviews)
"There was little food at breakfast. Waffle maker not available."

Reviewed on 2 Jun, 2025

AmericInn by Wyndham Osage
Country Trails Inn & Suites
Country Trails Inn & Suites
2 out of 5
809 U.S. 52, Preston, MN
Fully refundableReserve now, pay when you stay
The price is S$179 per night from 22 Jun to 23 Jun
S$179
22 Jun - 23 Jun
includes taxes & fees
9.4/10 Exceptional! (69 reviews)
"Very nice"

Reviewed on 29 May, 2025

Country Trails Inn & Suites
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 S$126 per night from 16 Jun to 17 Jun
S$126
16 Jun - 17 Jun
includes taxes & fees
8/10 Very Good! (389 reviews)
"easy access to main road and close to downtown with many dining options!!"

Reviewed on 10 Jun, 2025

Americas Best Value Inn & Suites Spring Valley
See all 28 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 holiday package cost?
Offering great value package deals on Expedia, you’ll be pleasantly surprised at how much a holiday to Chester costs! Expedia’s packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Chester?
If you’re looking to score a cheap Chester holiday 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 travellers.
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 holiday 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 personalise your search by “Property class,” “Number of bedrooms,” “Traveller 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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Chester holiday as a package?
You can enjoy significant savings on your next Chester getaway by booking a customised holiday 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 holiday 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 favourite time of year and the activities on offer will also help you decide when to holiday 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 holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.