Chester Holidays

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Top hotels in Chester

Royal River Casino and Hotel

Royal River Casino and Hotel

3 out of 5
607 S Veterans St Flandreau SD
Fully refundableReserve now, pay when you stay
The price is €94 per night from 16 Aug to 17 Aug
€94
16 Aug - 17 Aug
includes taxes & fees
8.6/10 Excellent! (644 reviews)
"Room was clean and roomy."

Reviewed on 15 Jul 2026

Royal River Casino and Hotel
Best Western Plus Lakeview Hotel

Best Western Plus Lakeview Hotel

2.5 out of 5
456 SE 12th Madison SD
Fully refundableReserve now, pay when you stay
The price is €132 per night from 30 Jul to 31 Jul
€132
30 Jul - 31 Jul
includes taxes & fees
9.4/10 Exceptional! (249 reviews)
"Clean, comfortable rooms."

Reviewed on 12 Jul 2026

Best Western Plus Lakeview Hotel
AmericInn by Wyndham Hartford SD

AmericInn by Wyndham Hartford SD

3 out of 5
1031 Diamond Circle Hartford SD
Fully refundableReserve now, pay when you stay
The price is €96 per night from 9 Aug to 10 Aug
€96
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (824 reviews)
"Very nice hotel close to I90 easy access. Clean, nice beds"

Reviewed on 14 Jul 2026

AmericInn by Wyndham Hartford SD
See all 38 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?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
January, February and November are great times to search for cheap Chester holiday packages. Travelling in quieter months means you'll typically find lower prices on flights and accommodation.
How many days is enough for Chester?
The ideal length for your Chester holiday depends on what you'd like to do. Typically, a few days to a week will give you plenty of time to check out all the top attractions and discover some hidden spots along the way.
How to find the best Chester package deals?
Use Expedia's filters to find some unbeatable Chester package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Chester package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Chester holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking flights and accommodation separately. Better still, you can tailor your Chester trip to fit your exact needs. Pick 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 holiday package to Chester?
If you've got your Chester travel dates finalized, book as early as you can to bag some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Chester?

  1. Pick your travel dates: What you plan to do in Chester and your favourite season can help you decide when to travel.
  2. Set a budget: Consider expenses like flights, food and transportation when working out how much to put aside for your trip to Chester. Then, choose a hotel that works with your budget, whether that's a wallet-friendly stay or a more luxurious retreat.
  3. Decide how long to go away for: Now that you're up to speed on Chester, you can work out the right length of your break. Put together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your airfare and accommodation: Once you've settled on your trip dates and duration, book the perfect Chester holiday package for you.

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