Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NZ$616 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

Chester Holiday

Our pick of the best Chester Hotel Deals

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 NZ$192 per night from 10 Aug to 11 Aug
NZ$192
10 Aug - 11 Aug
includes taxes & fees
9.4/10 Exceptional! (249 reviews)
"Comfortable"

Reviewed on 30 Jun. 2025

AmericInn by Wyndham Osage
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 NZ$163 per night from 13 July to 14 July
NZ$163
13 July - 14 July
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 2 Jul. 2025

Americas Best Value Inn & Suites Spring Valley
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 NZ$109 per night from 17 July to 18 July
NZ$109
17 July - 18 July
includes taxes & fees
6.4/10 (23 reviews)
"Bed clunked everytime I moved"

Reviewed on 22 Jun. 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 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.