Chester Vacations from $566

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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.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
AmericInn by Wyndham Windom

AmericInn by Wyndham Windom

3 out of 5
Price was $635, price is now $566 per person
$566
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Sioux Falls (FSD)
8.6/10 Excellent! (269 reviews)
Circuit breaker kept tripping from my oxygen concentrator, changed rooms still occurred. Never had a problem anywhere else. Staff said they had a lightning strike a few years back and have electrical problems since. Should be something the hotel should look into.

Reviewed on Feb 2, 2026

Historic Twin Tudors Inn

Historic Twin Tudors Inn

3 out of 5
Price was $1,096, price is now $958 per person
$958
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Sioux Falls (FSD)
8.8/10 Excellent! (3 reviews)
We were upgraded to staying at the Victorian Inn- i would highly recommended. The house is charming and located in the historic downtown of Sioux Falls.

Reviewed on Jun 16, 2025

Bilmar Inn & Suites Dell Rapids Near Sioux Falls

Bilmar Inn & Suites Dell Rapids Near Sioux Falls

2 out of 5
Price was $682, price is now $624 per person
$624
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Sioux Falls (FSD)
7/10 Good! (325 reviews)
I would give a higher rating but the beds were INCREDIBLY uncomfortable. The Old, worn out mattresses need an update

Reviewed on Jun 15, 2026

Clubhouse Hotel Suites Sioux Falls

Clubhouse Hotel Suites Sioux Falls

3 out of 5
Mall District
Price was $905, price is now $828 per person
$828
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Sioux Falls (FSD)
9.6/10 Exceptional! (1,071 reviews)
What an outstanding surprise was tonfins this hotel in our road trip! Amazing for families.

Reviewed on Jun 26, 2026

GLō Best Western Dawley Farms In Sioux Falls

GLō Best Western Dawley Farms In Sioux Falls

3 out of 5
Price was $681, price is now $632 per person
$632
per person
Sep 6 - Sep 9
found 10 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Sioux Falls (FSD)
9/10 Wonderful! (895 reviews)
Everything is great！It will be perfect if the swimming pool is heated. Girls in the front are sweet and helpful. Will be back for sure!

Reviewed on Jun 19, 2026

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Chester Hotel Deals

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
$105 nightly
The price is $120 total per night from Jun 28 to Jun 29
$120 total
Jun 28 - Jun 29
Total with taxes and fees
8.6/10 Excellent! (631 reviews)
"I liked that you have to use the key to access the putside doors, however the parking lot was very dark."

Reviewed on Jun 22, 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
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $110 total per night from Jul 5 to Jul 6
$110 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (818 reviews)
"When we checked in with another couple we were placed at opposite ends of the motel even after we requested to be close to each other. Then after checking into one of the rooms there was water all over the bathroom floor and it smelled to pee, so they were moved to another room. Then as we were trying ..."

Reviewed on Jun 22, 2026

AmericInn by Wyndham Hartford SD
Beautiful year round lake home! Sleeps 8 comfortably!

Beautiful year round lake home! Sleeps 8 comfortably!

Lake View Township SD
10/10 Exceptional! (42 reviews)
"Great place and was very clean!"

Reviewed on Jun 2, 2026

Get rates
Beautiful year round lake home! Sleeps 8 comfortably!
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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sioux Falls Regional Airport (FSD)
Top Sights
Lake Madison, Walkers Point Recreation Area and Lakes Golf Course

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Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this popular destination from $566 on Expedia. However, how much your vacation to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
If you're looking to book a cheap Chester vacation package, consider visiting in July, November and December. You'll typically find better rates on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Chester?
Generally, a handful of days is enough to visit the top attractions during your Chester vacation. However, if you'd like to have time to kick back or go on day trips, think about extending your itinerary.
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 vacation package as soon as possible.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations 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 vacation 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.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Secure your ideal getaway to Chester with Expedia's Book Now, Pay Later vacations. There's no need to save up or wait for your next paycheck — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stick to your budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.