Chester Vacation Packages

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Your Chester Vacation

Take the worry out of organizing your next big adventure with a Chester vacation 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 favorite places to visit. A few clicks is all it takes to put together a tailored Chester vacation on Expedia.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Beresford

Super 8 by Wyndham Beresford

2 out of 5
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Québec (YQB) to Sioux Falls (FSD)
6.4/10 (259 reviews)
The king suite was big and very nice.

Reviewed on Jul. 22, 2025

Days Inn by Wyndham North Sioux City

Days Inn by Wyndham North Sioux City

2 out of 5
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Québec (YQB) to Sioux Falls (FSD)
6.6/10 (550 reviews)
Cable kept loading could not watch tv

Reviewed on Jul. 21, 2025

Holiday Inn Express Hotel & Suites Vermillion by IHG

Holiday Inn Express Hotel & Suites Vermillion by IHG

2.5 out of 5
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Québec (YQB) to Sioux Falls (FSD)
8.4/10 Very Good! (349 reviews)
Staff was great and accommodating, rooms were clean and the amenities in the room with a microwave and fridge was great. Nice gym. Breakfast had variety. great place to stay.

Reviewed on May 27, 2025

Prairie Inn

Prairie Inn

2 out of 5
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Québec (YQB) to Sioux Falls (FSD)
7.2/10 Good! (318 reviews)
Nice for a less expensive hotel. Nothing fancy but clean, good breakfast.

Reviewed on Jul. 20, 2025

Red Roof Inn Vermillion - U of South Dakota

Red Roof Inn Vermillion - U of South Dakota

2 out of 5
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Québec (YQB) to Sioux Falls (FSD)
8/10 Very Good! (381 reviews)
This is a great budget, friendly accommodation which met all of our expectations. Rooms were clean and updated furniture and decor. The complementary breakfast was more than expected. As well as cereal and muffins, they had eggs, sausage, waffles, and toast, to name a few things. Very friendly staff. Highly recommended if you are looking for a budget friendly place to stay.

Reviewed on Jul. 20, 2025

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

AmericInn by Wyndham Hartford SD

AmericInn by Wyndham Hartford SD

2.5 out of 5
1031 Diamond Circle, Hartford, SD
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Jul 28 to Jul 29
CA $139
CA $151 total
Jul 28 - Jul 29
includes taxes & fees
9.2/10 Wonderful! (725 reviews)
Gem of a Hotel
"Fabulous staff, clean, comfortable, well maintained room and hotel. There is road construction in the area, but that did not impact my stay. I'd definitely stay again!"

Reviewed on Jul. 23, 2025

AmericInn by Wyndham Hartford SD
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 CA $117 per night from Jul 28 to Jul 29
CA $117
CA $148 total
Jul 28 - Jul 29
includes taxes & fees
8.4/10 Very Good! (507 reviews)
"It was nice clean and quiet"

Reviewed on Jul. 18, 2025

Royal River Casino and Hotel
Bilmar Inn & Suites Dell Rapids

Bilmar Inn & Suites Dell Rapids

2 out of 5
510 N Highway 77, Dell Rapids, SD
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from Jul 29 to Jul 30
CA $109
CA $119 total
Jul 29 - Jul 30
includes taxes & fees
6.8/10 (288 reviews)
"it was not bad the room hot tub could have been cleaned better. the king bed not the most comfortable but for the price per night it was good."

Reviewed on Jul. 20, 2025

Bilmar Inn & Suites Dell Rapids
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this top destination from CA $980 on Expedia. However, how much your vacation to Chester costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Chester?
If you're hoping to book a cheap Chester vacation package, consider travelling in January, February and November. You'll typically find better prices on hotels and flights during these months — ideal for budget-conscious travellers.
How many days is enough for Chester?
The ideal length for your Chester vacation depends on what you'd like to do. Typically, a handful of days to a week will give you time to hit all the top sights and explore some hidden treasures along the way.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Chester package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chester getaway off to a flying start.
Is it cheaper to book a Chester vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still have the freedom to create a personalized Chester vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Chester?
If you're planning a spur-of-the-moment Chester adventure, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Chester?

  1. Choose when to go: Check your diary and pack your bags. Your favourite season and the type of activities on offer will also help you decide when to visit Chester.
  2. Set a budget: Factor in expenses such as flights, meals and transportation when calculating how much to put aside for your trip to Chester. Then, pick a hotel that works with your budget, whether that's an economical stay or a deluxe retreat.
  3. Decide how long to go for: Now that you're more familiar with Chester, you can work out the perfect length of your break. Create a rough plan and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Chester vacation package.

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