Book Hotels in Chester, SD
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Top Chester hotels

Spacious 6BR Lakefront Cabin - Beach Access & Stunning Views on Lake Madison
Lake Madison SD
This vacation home featured laundry facilities and barbecue grills.
Great cabin in a unique location on the peninsula. Views to the water in front and back of the property. Lots of room to spread out and enjoy with family.
Reviewed on Mar 15, 2026

Beautiful year round lake home! Sleeps 8 comfortably!
Lake View Township SD
This vacation home featured laundry facilities and barbecue grills.
Great location.
Reviewed on Mar 2, 2026

Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!
Wentworth SD
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Peaceful property and very responsive host
Reviewed on Apr 27, 2026

Best Western Plus Lakeview Hotel
456 SE 12th Madison SD
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $153 total per night from May 17 to May 18
$153 total
May 17 - May 18
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 ...
Nicest place in Madison
Reviewed on May 8, 2026

AmericInn by Wyndham Hartford SD
1031 Diamond Circle Hartford SD
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $92 total per night from May 24 to May 25
$92 total
May 24 - May 25
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 ...
Stay again and would recommend for one night. Good breakfast.
Reviewed on Apr 26, 2026

Royal River Casino and Hotel
607 S Veterans St Flandreau SD
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $120 total per night from May 10 to May 11
$120 total
May 10 - May 11
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. ...
I spent 3 night and apparently there little to no room service. Coffee pot not cleaned, no coffee replaced, no towels replenished, bed made only one day, light blew out on the 3rd night, garbage not removed. Strong tobacco smell throughout other than the new wing.
Reviewed on May 7, 2026

AmericInn by Wyndham Madison SD
504 SE 10th St Madison SD
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $88 total per night from May 10 to May 11
$88 total
May 10 - May 11
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 ...
I stayed the night of May 5th and had stayed at this property several times as I have a student at DSU. This was by far the worst and I am considering cancelling my future reservations. The TV did not work initially (no signal) and the person who came to fix it Tuesday evening around 8 PM spent more ...
Reviewed on May 7, 2026

Bilmar Inn & Suites Dell Rapids Near Sioux Falls
510 N Highway 77 Dell Rapids SD
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $96 total per night from May 13 to May 14
$96 total
May 13 - May 14
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.
There was bed bugs. We immediately left but have been fighting for a refund. There was stains all over the mattress and it was gross.
Reviewed on Apr 24, 2026

Super 8 by Wyndham Madison
219 N Highland Ave Madison SD
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $77 total per night from May 11 to May 12
$77 total
May 11 - May 12
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 ...
Friendly helpful staff and clean facilities
Reviewed on Apr 29, 2026
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
Recent Chester hotel reviews by fellow wanderers

Best Western Plus Lakeview Hotel
4 out of 5
Posted 13 hours ago
Travelocity Verified Review
"Nicest place in Madison "
A verified traveler stayed at Best Western Plus Lakeview Hotel
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