Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Packages with flights are ATOL protected

Your Chester Holiday

Take the worry out of organising your next big adventure with a Chester holiday package. Whether you're lured here by its food, entertainment or other highlights, this city offers countless exciting experiences to delve into. Make sure to spend time sightseeing during your trip to Chester. Lake Madison and Lakes Golf Course are some favourite places to visit. A few clicks is all it takes to put together a tailored Chester holiday on Expedia.

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sioux Falls Regional Airport (FSD)
Max Temp Winter
-3.89ºC
Max Temp Summer
27ºC
Top Sights
Lake Madison, Walkers Point Recreation Area and Lakes Golf Course

Top hotels in Chester

4-bedroom 3 bath lakefront home on Brandt Lake

4-bedroom 3 bath lakefront home on Brandt Lake

Chester SD
10/10 Exceptional! (1 review)
"Great location as well as the additional amenities to create a getaway without the fuss of hauling all the toys."

Reviewed on 7 Sept 2026

Get rates
4-bedroom 3 bath lakefront home on Brandt Lake
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 £72 per night from 8 Nov to 9 Nov
£72
8 Nov - 9 Nov
includes taxes & fees
8.6/10 Excellent! (693 reviews)
"all is well"

Reviewed on 3 Nov 2026

Royal River Casino and Hotel
AmericInn by Wyndham Hartford SD

AmericInn by Wyndham Hartford SD

3 out of 5
1031 Diamond Circle Hartford SD
The price is £67 per night from 29 Nov to 30 Nov
£67
29 Nov - 30 Nov
includes taxes & fees
AmericInn by Wyndham Hartford SD
See all 37 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chester travel package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Chester from just . And the more you bundle, the more you save. The getaway of your dreams has never been so affordable.
If I'm not able to travel, can I cancel my Chester travel package?
Don't worry if you're rethinking your Chester travel package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We get that your circumstances can change suddenly, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to Chester?
Browse and book everything in the one place with our Chester holiday packages. You'll discover deals on hotels, flights and more that'll keep your credit card happy and adventurous side satisfied. And, with more than 550 air carriers and 1,000,000 hotels across the globe to select from, you'll have the flexibility to mix and match however you please.
Does Expedia offer Book Now, Pay Later Chester holidays?
Expedia has partnered with online lender Klarna to make your next getaway easier on your bank balance. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more money to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Browse these flexible payment options:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that work for all types of budgets, so you can lock in that well-earned holiday now.
  • Pay in instalments holidays: If you'd prefer to pay for your getaway in multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you see an awesome deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you get what you want.

What are the top hotels in Chester?
Book a room at Best Western Plus Lakeview Hotel. It's one of this area's most popular properties. Another well-known option in Chester is AmericInn by Wyndham Madison SD.
How far in advance should I book my Chester holiday?
It's hard to pick the perfect time for airfares, but we generally suggest the earlier, the better. Many international flights on Expedia become available to compare up to 12 months in advance. If you're booking last minute, don't stress. Discounted prices appear from time to time just weeks before departure dates.
What does an Expedia Chester travel package include?
Hotels, flights and rental cars — we've got them all. With Expedia, you can create your Chester package the way you want. All you have to do is decide what you need. Once you've made your booking, you can add extras like activities and tours. The more you bundle, the greater the savings!
What should I know before booking a Chester travel package?
A package can be more affordable than separately booking everything you need for your getaway. For example, bundle your hotels, flights and rental cars and save a pretty penny. No matter your holiday plans, there's sure to be a package within your budget.
Can I choose my airline with a Chester Expedia travel package?
Expedia has access to more than 550 partner airlines worldwide, so you certainly can. Simply choose the carrier you want and create the perfect Chester trip.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.