Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Valley Inn

Valley Inn

2.5 out of 5
University Heights
Price was $491, price is now $418 per person
$418
per person
Jan 27 - Jan 31
just found
Roundtrip non-stop flight included
Grand Rapids (GRR) to Sioux Falls (FSD)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a picnic area, and luggage storage are also on offer.
Canopy By Hilton Sioux Falls Downtown

Canopy By Hilton Sioux Falls Downtown

4 out of 5
Downtown Sioux Falls
Price was $744, price is now $580 per person
$580
per person
Jan 27 - Jan 31
just found
Roundtrip non-stop flight included
Grand Rapids (GRR) to Sioux Falls (FSD)
A restaurant and a 24-hour gym are featured at this hotel. WiFi in public areas is free. Self parking is offered and the front desk is staffed around-the-clock.
Country Inn & Suites by Radisson, Sioux Falls, SD

Country Inn & Suites by Radisson, Sioux Falls, SD

3 out of 5
Downtown Sioux Falls
Price was $570, price is now $458 per person
$458
per person
Jan 27 - Jan 31
just found
Roundtrip non-stop flight included
Grand Rapids (GRR) to Sioux Falls (FSD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free continental breakfast each morning.
AeroStay Hotel

AeroStay Hotel

2.5 out of 5
North Sioux Falls
Price was $639, price is now $543 per person
$543
per person
Jan 27 - Jan 31
just found
Roundtrip non-stop flight included
Grand Rapids (GRR) to Sioux Falls (FSD)
A 24-hour gym is featured at this hotel, along with self parking. Enjoy the free on-the-go breakfast each morning. Traveling on business? Take advantage of the 2 conference rooms, along with the 24-hour business center.
Clarion Pointe Sioux Falls Airport

Clarion Pointe Sioux Falls Airport

2.5 out of 5
Northwest Sioux Falls
Price was $555, price is now $473 per person
$473
per person
Jan 27 - Jan 31
just found
Roundtrip non-stop flight included
Grand Rapids (GRR) to Sioux Falls (FSD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and free perks like buffet breakfast and free self parking.

Top Chester hotels deals

AmericInn by Wyndham Hartford SD

AmericInn by Wyndham Hartford SD

2.5 out of 5
1031 Diamond Circle Hartford SD
Free Cancellation
Reserve now, pay when you stay
$82 nightly
The price is $90 total per night
$90 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Royal River Casino and Hotel

Royal River Casino and Hotel

3 out of 5
607 S Veterans St Flandreau SD
$105 nightly
The price is $120 total per night
$120 total
Dec 23 - Dec 24
Total with taxes and fees
A casino and a restaurant are featured at this traditional hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A snack bar/deli, luggage storage, and wedding services are also on offer.
Parking included
Free WiFi
AmericInn by Wyndham Madison SD

AmericInn by Wyndham Madison SD

2.5 out of 5
504 SE 10th St Madison SD
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $98 total per night
$98 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the indoor pool and conveniences like a 24-hour front desk and laundry facilities.
Pool
Breakfast included
Best Western Plus Lakeview Hotel

Best Western Plus Lakeview Hotel

2.5 out of 5
SE QUAD OF HWY 34 AND WASHINGTON AVE Madison SD
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $140 total per night
$140 total
Dec 29 - Dec 30
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like on-the-go breakfast and free self parking.
Pool
Breakfast included
Bilmar Inn & Suites by Hotel O Hwy 77

Bilmar Inn & Suites by Hotel O Hwy 77

2 out of 5
510 N Highway 77 Dell Rapids SD
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $95 total per night
$95 total
Dec 23 - Dec 24
Total with taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. Express check-out is also provided.
Pet friendly
Parking included
Super 8 by Wyndham Madison

Super 8 by Wyndham Madison

2 out of 5
219 N Highland Ave Madison SD
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $88 total per night
$88 total
Dec 23 - Dec 24
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the laundry service. The front desk is staffed around-the-clock and laundry facilities are on offer.
Breakfast included
Pet friendly
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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.

Frequently asked questions

How much are vacation packages to Chester?
With offers starting from as little as $418, hotel and flight packages are a superb way to stretch your travel budget. Get ready Chester — here you come!
Where can I get the best vacation package deals for Chester?
You can grab amazing Chester package deals with Travelocity. Choose from as many as 400 air carriers and 1,000,000 properties worldwide and turn those travel fantasies into reality.
Why should I purchase my Chester vacation package with Travelocity?
We offer round-the-clock support, high-quality service and a Price Match Guarantee. Life's a big journey — and we have amazing destinations for you to journey to in every nook and cranny of the globe. Wander with us and your bank balance will thank you for it.
Will I save money on my Chester car rental if I book it with a hotel or flight?
You can with our Chester vacation packages. With one of these, there are lots of ways to stretch your budget further. Bundle any two or more car, flight, hotel and tour bookings and watch your savings start to grow. With a rental car, all the attractions around Chester are within reach.
Which airport is best for Chester?
Sioux Falls Regional Airport (FSD) is about 25 mi southeast of downtown Chester.
Where should I stay when visiting Chester?
The Relaxing and peaceful cabin on Brant Lake is the first choice of many travelers. Book now before it's too late.

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