Chester Vacations from $411

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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.
Historic Victorian Inn

Historic Victorian Inn

3 out of 5
Cathedral
Price was $538, price is now $411 per person
$411
per person
Feb 5 - Feb 8
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
8.8/10 Excellent! (56 reviews)
No staff present. Remote guy emailed us like 20 times. Unexpected fee of $300 deposit. I think that’s a bit excessive. So so many rules. I was literally afraid to touch anything. House is ready for serious restoration. Could be a really fabulous place. I wouldn’t stay there again.

Reviewed on Jul 11, 2025

Historic Twin Tudors Inn

Historic Twin Tudors Inn

3 out of 5
Save 100% on your flight
Price was $807, price is now $539 per person
$539
per person
Feb 5 - Feb 8
found 9 hours ago
Roundtrip flight included
Denver (DEN) 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

Canopy By Hilton Sioux Falls Downtown

Canopy By Hilton Sioux Falls Downtown

4 out of 5
Downtown Sioux Falls
Price was $579, price is now $439 per person
$439
per person
Feb 5 - Feb 8
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
9.4/10 Exceptional! (148 reviews)
Beautiful, clean room with amazing view of the falls area. Coffee maker Espresso superb! Decor over the top amazing!!! Only reason not an excellent was that the shower as beautiful as it was barely got warm. Lovely visit overall and the food options were fantastic!!

Reviewed on Dec 13, 2025

Hotel On Phillips

Hotel On Phillips

2.5 out of 5
Downtown Sioux Falls
Price was $605, price is now $484 per person
$484
per person
Feb 5 - Feb 8
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
9.6/10 Exceptional! (1,271 reviews)
Staff was VERY accommodating and super friendly. Valet parking. Underground parking.

Reviewed on Dec 7, 2025

AeroStay Hotel

AeroStay Hotel

2.5 out of 5
North Sioux Falls
Price was $546, price is now $439 per person
$439
per person
Feb 5 - Feb 8
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
8.8/10 Excellent! (1,009 reviews)
Breakfast was not breakfast disappointed way to leave for a flight in

Reviewed on Dec 10, 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 Dec 15 to Dec 16
$120 total
Dec 15 - Dec 16
Total with taxes and fees
8.4/10 Very Good! (568 reviews)
Hotel is clean, nice and quiet. The breakfast was delicious.

Reviewed on Nov 4, 2025

Royal River Casino and Hotel
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
$83 nightly
The price is $91 total per night from Dec 28 to Dec 29
$91 total
Dec 28 - Dec 29
Total with taxes and fees
9/10 Wonderful! (780 reviews)
2nd stay here - great airport location. My only complaint is low pressure in shower. Quiet and comfy room.

Reviewed on Nov 3, 2025

AmericInn by Wyndham Hartford SD
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
$89 nightly
The price is $99 total per night from Dec 15 to Dec 16
$99 total
Dec 15 - Dec 16
Total with taxes and fees
7.6/10 Good! (354 reviews)
The hotel was great. Fast and friendly service at the front desk. Room was clean and spacious. Bathroom was spotless. Bed was a little hard for my liking. Easy access. Lots of places to park. Would stay again.

Reviewed on Nov 9, 2025

AmericInn by Wyndham Madison 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.

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 $411 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.