Book Hotels in Chester, SD
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Top Chester hotels

Lake Madison Condo
Wentworth SD
This condo features a garden, laundry facilities, and barbecue grills.
"Peaceful Lakeside Retreat"Absolutely loved our stay! The property is right on the lake, offering stunning views and total tranquility. Just a short walk away is a lovely bar and restaurant—perfect for relaxing evenings. Everything about this place was peaceful, quiet, and exactly what we needed. ...
Reviewed on Sep 2, 2025

Best Western Plus Lakeview Hotel
SE QUAD OF HWY 34 AND WASHINGTON AVE Madison SD
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $140 total per night from Jan 29 to Jan 30
$140 total
Jan 29 - Jan 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 ...
The room was very nice. The breakfast was great. What stood out the most was the kindness of the staff. When I first checked in the lady at the front desk was especially kind and thoughtful.
Reviewed on Jan 11, 2026

Unique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.
Buffalo Ridge SD
This vacation home features a water park, laundry facilities, and barbecue grills.
Lots of room inside and plenty of parking space. Well arranged for a large group visiting and dining. Very noisy outside with almost constant traffic on Hwy 38. Could use some repairs and cleanup on the outside.
Reviewed on Aug 9, 2025

AmericInn by Wyndham Hartford SD
1031 Diamond Circle Hartford SD
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $88 total per night from Feb 1 to Feb 2
$88 total
Feb 1 - Feb 2
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 ...
The breakfast was really very good. I should have given it a 5.
Reviewed on Jan 5, 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 Jan 25 to Jan 26
$120 total
Jan 25 - Jan 26
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. ...
Exceptional on housekeeping and staff
Reviewed on Dec 29, 2025

Beautiful large lake home for a family retreat, have fun by the water!
Wentworth SD
This vacation home featured laundry facilities and barbecue grills.
Our family had a great experience staying at the home over the Labor Day holiday. We were a large group, and the house provided us plenty of space indoors & out. The owners were great to work with and very accommodating.
Reviewed on Sep 3, 2025

AmericInn by Wyndham Madison SD
504 SE 10th St Madison SD
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Jan 25 to Jan 26
$92 total
Jan 25 - Jan 26
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 ...
The hotel was nice enough but the sheets pillows and towels have to be original to when it was built..... They are stained and very thin.... Spend a little money replacing the linens and it would be a much better experience....
Reviewed on Dec 25, 2025

Bilmar Inn & Suites by Hotel O Hwy 77
510 N Highway 77 Dell Rapids SD
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $92 total per night from Jan 23 to Jan 24
$92 total
Jan 23 - Jan 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.
Room was clean and host very helpful!
Reviewed on Jan 6, 2026

Spacious 6BR Lakefront Cabin - Beach Access & Stunning Views on Lake Madison
Lake Madison SD
This vacation home featured laundry facilities and barbecue grills.
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
5 out of 5
Posted 11 days ago
Travelocity Verified Review
"The room was very nice. The breakfast was great. What stood out the most was the kindness of the staff. When I first checked in the lady at the front desk was especially kind and thoughtful."
A verified traveler stayed at Best Western Plus Lakeview Hotel
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