Chester Vacations from $335

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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.
Microtel Inn & Suites by Wyndham Sioux Falls

Microtel Inn & Suites by Wyndham Sioux Falls

2 out of 5
Price was $408, price is now $335 per person
$335
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
6.6/10 (1,004 reviews)
It was clean and nice.

Reviewed on Sep 27, 2025

Historic Twin Tudors Inn

Historic Twin Tudors Inn

3 out of 5
Save 100% on your flight
Price was $1,013, price is now $731 per person
$731
per person
Dec 3 - Dec 7
found 16 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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

Hotel On Phillips

Hotel On Phillips

2.5 out of 5
Downtown Sioux Falls
Price was $661, price is now $512 per person
$512
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
9.6/10 Exceptional! (1,190 reviews)
Very nice hotel and comfy beds, but aside from the valet, the two individuals we encountered at the front desk may have been the most least friendly individuals I've ever encountered at any hotel front desk. Not one smile nor nice word (how about "welcome" or " enjoy your stay" or even ask " how was your stay & goodbye", I would even have accepted a smile.

Reviewed on Sep 24, 2025

Gateway Park Hotel and Suites

Gateway Park Hotel and Suites

2.5 out of 5
Price was $513, price is now $406 per person
$406
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
9.2/10 Wonderful! (1,003 reviews)
Was very impressed with staff. Very nice people

Reviewed on Sep 23, 2025

Ramada by Wyndham Sioux Falls Airport-Waterpark & Event Ctr

Ramada by Wyndham Sioux Falls Airport-Waterpark & Event Ctr

3 out of 5
Price was $533, price is now $442 per person
$442
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
7.6/10 Good! (1,388 reviews)
Staff were pleasant. Could be a bit more clean inside and outside on property. Will continue to stay here!

Reviewed on Sep 23, 2025

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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 Sep 28 to Sep 29
$120 total
Sep 28 - Sep 29
Total with taxes and fees
8.4/10 Very Good! (528 reviews)
"We had a king suite and it was an amazing room! We couldn’t have been more comfortable!"

Reviewed on Sep 21, 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
$78 nightly
The price is $85 total per night from Oct 6 to Oct 7
$85 total
Oct 6 - Oct 7
Total with taxes and fees
6.8/10 (296 reviews)
"Staff was outstanding!"

Reviewed on Jul 31, 2025

Bilmar Inn & Suites Dell Rapids
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
$88 nightly
The price is $96 total per night from Oct 19 to Oct 20
$96 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (760 reviews)
"Nice place."

Reviewed on Sep 24, 2025

AmericInn by Wyndham Hartford SD
See all 29 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.

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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 $335 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.