Chester Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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 S$162 per night from 1 Dec to 2 Dec
S$162
includes taxes & fees
1 Dec - 2 Dec
8.4/10 Very Good! (430 reviews)
Good stay!
"We enjoyed our stay. Clean room, buffet was great."

Reviewed on 11 Nov,2024

Royal River Casino and Hotel
AmericInn by Wyndham Madison SD
AmericInn by Wyndham Madison SD
2.5 out of 5
504 SE 10th St, Madison, SD
Fully refundableReserve now, pay when you stay
The price is S$120 per night from 24 Nov to 25 Nov
S$120
includes taxes & fees
24 Nov - 25 Nov
8/10 Very Good! (272 reviews)
"Great place to stay. Staff was cordial. Clean and quiet."

Reviewed on 7 Nov,2024

AmericInn by Wyndham Madison SD
Best Western Plus Lakeview Hotel
Best Western Plus Lakeview Hotel
2.5 out of 5
SE QUAD OF HWY 34 AND WASHINGTON AVE, Madison, SD
Fully refundableReserve now, pay when you stay
The price is S$203 per night from 1 Dec to 2 Dec
S$203
includes taxes & fees
1 Dec - 2 Dec
9.4/10 Exceptional! (176 reviews)
"Friendly staff, good breakfast options."

Reviewed on 14 Nov,2024

Best Western Plus Lakeview Hotel
See all 23 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?
Much less than you might think — from a tempting , in fact! By combining hotels, flights and car rentals into a custom-made package, your getaway to Chester is only clicks away.
How do I get a cheap travel package to Chester?
Browse and book everything in one place with our Chester holiday packages. You’ll discover bargains on hotels, flights, tours and more that’ll keep your budget happy and your adventurous spirit alive. And, with more than 550 airlines and 1,000,000 hotel options all over the world to choose from, you’ll have the flexibility to mix and match as you please.
How far in advance should I book my Chester holiday?
Savvy travellers book early. Airlines generally release flights around a year in advance, and this is an excellent opportunity to land some of the cheapest prices. Boss just told you to take some holiday time next month? Don’t fret. Expedia are never short of fantastic bargains to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Chester travel package include?
Flights, hotels and a reliable car for all your road trip adventures. Simply choose your favourite bundle and gain access to great discounts. Once you’ve made your booking, add on a few tours and activities and watch your savings pile up. When it comes to organising your Chester holiday, you’re in charge!
What should I know before booking a Chester travel package?
When you book your hotels, flights and car rentals together, you’ll be rewarded with fantastic discounts. Whether you’re organising a beach escape in a villa or would rather stay in an upscale city hotel, Expedia can help make it happen.
Can I choose my airline with a Chester Expedia holiday package?
With a holiday package, the choice is in your hands. Whether you’re hoping to fly to Chester in coach or first class, simply pick from the available airline options. Expedia has access to over 550 partner airlines all over the world.
If I'm not able to travel, can I cancel my Chester holiday package?
You can. We totally understand that even the best-laid plans can fail, so we’re here to help if you have to make changes to your Chester holiday package. You may be able to cancel or change your itinerary for free if you’ve booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Look up our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.

* 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.