Chester Vacations from $345

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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.
Bilmar Inn & Suites Dell Rapids Near Sioux Falls

Bilmar Inn & Suites Dell Rapids Near Sioux Falls

2 out of 5
Price was $429, price is now $345 per person
$345
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
7/10 Good! (310 reviews)
Clean and friendly also just off interstate

Reviewed on Dec 1, 2025

Historic Twin Tudors Inn

Historic Twin Tudors Inn

3 out of 5
Price was $805, price is now $601 per person
$601
per person
Apr 23 - Apr 26
found 1 day 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

Hotel On Phillips

Hotel On Phillips

2.5 out of 5
Downtown Sioux Falls
Price was $566, price is now $473 per person
$473
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
9.6/10 Exceptional! (1,353 reviews)
As always the Hotel on Phillips does not disappoint. Convenient location with many dining and shopping options near by.

Reviewed on Mar 7, 2026

Gateway Park Hotel and Suites

Gateway Park Hotel and Suites

2.5 out of 5
Price was $459, price is now $391 per person
$391
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
9.2/10 Wonderful! (1,001 reviews)
Staff friendly, clean and grandson enjoyed the pool.

Reviewed on Feb 23, 2026

AeroStay Hotel

AeroStay Hotel

2.5 out of 5
North Sioux Falls
Price was $505, price is now $437 per person
$437
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sioux Falls (FSD)
8.8/10 Excellent! (1,072 reviews)
room was clean was easy to checkin love the convenience of flying out

Reviewed on Mar 5, 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 Mar 8 to Mar 9
$120 total
Mar 8 - Mar 9
Total with taxes and fees
8.6/10 Excellent! (580 reviews)
Yes it was wonderful

Reviewed on Mar 7, 2026

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
$72 nightly
The price is $80 total per night from Mar 8 to Mar 9
$80 total
Mar 8 - Mar 9
Total with taxes and fees
7.8/10 Good! (367 reviews)
The bathroom floor was dirty. The breakfast was very minimal compared to the advertised amenity. The pool had no heat, the pool room had no heat so unusable!

Reviewed on Mar 2, 2026

AmericInn by Wyndham Madison SD
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
$82 nightly
The price is $89 total per night from Mar 22 to Mar 23
$89 total
Mar 22 - Mar 23
Total with taxes and fees
AmericInn by Wyndham Hartford SD
See all 41 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 $345 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.