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Top Chester hotels

4-bedroom 3 bath lakefront home on Brandt Lake

4-bedroom 3 bath lakefront home on Brandt Lake

Chester SD
This vacation home featured laundry facilities and barbecue grills.
"Great location as well as the additional amenities to create a getaway without the fuss of hauling all the toys."

Reviewed on Sep 7, 2026

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Opens in a new window4-bedroom 3 bath lakefront home on Brandt Lake
Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!

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.
"Was a great time, property was as described."

Reviewed on Sep 3, 2026

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Opens in a new windowLakeside Getaway on Lake Madison. Hot tub with a view of the lake!
Unique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.

Unique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.

Buffalo Ridge SD
This vacation home featured laundry facilities and barbecue grills.
"We loved celebrating the Bride to Be at the cabin. It was so pretty and close to everything we had planned."

Reviewed on Aug 2, 2026

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Opens in a new windowUnique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.
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
$94 nightly
The price is $108 total per night from Oct 13 to Oct 14
$108 total
Oct 13 - Oct 14
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. ...
"We stayed in a king suite - the room was beautiful and clean. The bed was slightly uncomfortable. There was hardly any water pressure in shower and the water seemed hard. We had the prime rib buffet and it was overcooked."

Reviewed on Oct 11, 2026

Opens in a new windowRoyal River Casino and Hotel
Bilmar Inn & Suites Dell Rapids Near Sioux Falls

Bilmar Inn & Suites Dell Rapids Near Sioux Falls

2 out of 5
510 N Highway 77 Dell Rapids SD
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $99 total per night from Oct 13 to Oct 14
$99 total
Oct 13 - Oct 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.
"Rooms clean. Lobby a little messy. Cold cereal for breakfast. Needs more attention to details throughout."

Reviewed on Sep 21, 2026

Opens in a new windowBilmar Inn & Suites Dell Rapids Near Sioux Falls
AmericInn by Wyndham Hartford SD

AmericInn by Wyndham Hartford SD

3 out of 5
1031 Diamond Circle Hartford SD
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $87 total per night from Oct 18 to Oct 19
$87 total
Oct 18 - Oct 19
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 ...
Opens in a new windowAmericInn by Wyndham Hartford SD
Best Western Plus Lakeview Hotel

Best Western Plus Lakeview Hotel

2.5 out of 5
456 SE 12th Madison SD
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $153 total per night from Oct 18 to Oct 19
$153 total
Oct 18 - Oct 19
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 ...
Opens in a new windowBest Western Plus Lakeview Hotel
AmericInn by Wyndham Madison SD

AmericInn by Wyndham Madison SD

3 out of 5
504 SE 10th St Madison SD
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $103 total per night from Nov 1 to Nov 2
$103 total
Nov 1 - Nov 2
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 ...
Opens in a new windowAmericInn by Wyndham Madison SD
Super 8 by Wyndham Madison

Super 8 by Wyndham Madison

2 out of 5
219 N Highland Ave Madison SD
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $75 total per night from Nov 8 to Nov 9
$75 total
Nov 8 - Nov 9
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 ...
Opens in a new windowSuper 8 by Wyndham Madison
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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

What are the top kid-friendly hotels in Chester?
Family getaways are where treasured memories are made, but it's no secret that traveling with young ones can be challenging. These kid-friendly Chester hotels come with perks that aim to keep old and young alike relaxed and happy: You're well catered for at Relaxing and peaceful cabin on Brant Lake. It comes with a playground, a travel crib and a flair for making families feel welcome. Alternatively, spend your nights in Chester at Lake Madison Condo. Make the most of a barbecue grill, internet access and more here.
Where can I find cheap hotels in Chester?
At Travelocity you'll find really nice hotels in Chester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chester rather than in Chester. We may find you even better rates, too.
How do I find the best Chester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chester?
The cheapest hotel in Chester is $75. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chester?
There are 39 hotels in Chester on Travelocity.
What are the best hotels in Chester?
Chester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chester for you!
When is the best time to visit Chester?
If you want the joy of a fun-filled trip in peak season, visit Chester during March, April and September. If you'd prefer the peace of off-season, book a stay during quieter months, such as July, November and December.
When is the cheapest time to stay in Chester?
Based on historic data is usually the cheapest month to visit Chester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chester?
There are multiple hotels in Chester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chester. We have plenty of kid-friendly hotels in Chester to choose from on Travelocity!
Why book a hotel in Chester through Travelocity?
Because we have the top hotels in Chester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chester hotel reviews by fellow wanderers

3+ night special | King Bed | Dog friendly + Fenced Yard | 3 TVs

3+ night special | King Bed | Dog friendly + Fenced Yard | 3 TVs

5 out of 5
Posted 2 weeks ago
Travelocity Verified Review
"Very cute and functional space. Hosts were great. The back sunroom was great to drink coffee and watch the squirrels. It was a very relaxing place to stay."
A verified traveler stayed at 3+ night special | King Bed | Dog friendly + Fenced Yard | 3 TVs
3+ night special | King Bed | Dog friendly + Fenced Yard | 3 TVs

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