Title: Book The Best Hotels in Chester, SD for 2026 from CA $102 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d553248635975872311.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d553248635975872311.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d553248635975872311.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Chester Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+South+Dakota%2C+United+States+of+America®ionId=553248635975872311&latLong=43.894913%2C-96.92656&adults=2&startDate=2026-02-12&d1=2026-02-12&endDate=2026-02-14&d2=2026-02-14&amenities=PETS) ## Check prices for these dates Tonight [Jan 29 - Jan 30](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 30 - Jan 31](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2026-01-30&endDate=2026-01-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels ![Lobby lounge](https://images.trvl-media.com/lodging/43000000/42650000/42640800/42640743/0d87aea2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42650000/42640800/42640743/5b7b337c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/43000000/42650000/42640800/42640743/0d63719f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42650000/42640800/42640743/e11a6b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Lakeview Hotel [](https://www.expedia.ca/Madison-Hotels-Best-Western-Plus-Lakeview-Hotel.h42640743.Hotel-Information) Madison 9.4/10 Exceptional (228 reviews) "Great place to stay. Clean rooms friendly staff and good breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn CA $200 CA $220 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Madison-Hotels-Best-Western-Plus-Lakeview-Hotel.h42640743.Hotel-Information) ![Desk, soundproofing, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/23000000/22720000/22714700/22714648/ec4d7248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/23000000/22720000/22714700/22714648/3ed3705a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22720000/22714700/22714648/38f3254d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/23000000/22720000/22714700/22714648/a3d5be32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AmericInn by Wyndham Madison SD [](https://www.expedia.ca/Madison-Hotels-AmericInn-By-Wyndham-Madison-SD.h22714648.Hotel-Information) Madison 7.8/10 Good (363 reviews) "Room was great lots of space" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet CA $110 CA $122 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Madison-Hotels-AmericInn-By-Wyndham-Madison-SD.h22714648.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/910000/908600/908526/ac136463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/908600/908526/fb6a9111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/910000/908600/908526/3985819b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/908600/908526/47162c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Madison [](https://www.expedia.ca/Madison-Hotels-Super-8-By-Wyndham-Madison.h908526.Hotel-Information) Madison 6.4/10 (262 reviews) "nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Virginia CA $91 CA $102 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Madison-Hotels-Super-8-By-Wyndham-Madison.h908526.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/37000000/36830000/36825600/36825572/52185064.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/37000000/36830000/36825600/36825572/494e64ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/37000000/36830000/36825600/36825572/15408b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/37000000/36830000/36825600/36825572/e8bf3f48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Royal River Casino and Hotel [](https://www.expedia.ca/Sioux-Falls-Hotels-Royal-River-Casino-And-Hotel.h36825572.Hotel-Information) Flandreau 8.6/10 Excellent (573 reviews) "Hotel is clean, nice and quiet. The breakfast was delicious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael [](https://www.expedia.ca/Sioux-Falls-Hotels-Royal-River-Casino-And-Hotel.h36825572.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/320000/317300/317203/3fe811a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/320000/317300/317203/edfc6690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/320000/317300/317203/96f06e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/320000/317300/317203/97cec007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bilmar Inn & Suites Dell Rapids Near Sioux Falls [](https://www.expedia.ca/Sioux-Falls-Hotels-Bilmar-Inn-Suites-Dell-Rapids.h317203.Hotel-Information) Dell Rapids 7.0/10 Good (309 reviews) "Clean and friendly also just off interstate" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin and Dianne [](https://www.expedia.ca/Sioux-Falls-Hotels-Bilmar-Inn-Suites-Dell-Rapids.h317203.Hotel-Information) ![Deluxe Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/10000000/9780000/9779900/9779853/aecaa147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/10000000/9780000/9779900/9779853/c7efc5cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/10000000/9780000/9779900/9779853/e134c47c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9780000/9779900/9779853/cf46fc7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AmericInn by Wyndham Hartford SD [](https://www.expedia.ca/Sioux-Falls-Hotels-AmericInn-By-Wyndham-Hartford-SD.h9779853.Hotel-Information) Hartford 9.2/10 Wonderful (788 reviews) "Great hotel value. Clean, cozy, friendly staff and nice breakfast bar" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Krista CA $114 CA $124 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Sioux-Falls-Hotels-AmericInn-By-Wyndham-Hartford-SD.h9779853.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-12&endDate=2026-02-13®ionId=553248635975872311&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d553248635975872311.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d553248635975872311.Travel-Guide-Hotels) ## Top Chester Hotel Reviews ![Beautiful year round lake home! Sleeps 8 comfortably!](https://images.trvl-media.com/lodging/84000000/83710000/83708300/83708290/c4ee9dbd_y.jpg) ### Beautiful year round lake home! Sleeps 8 comfortably! 10/10 Excellent "Convenient location right on lake. Picturesque sunrises over Lake Madison. " [](https://expedia.ca/Madison-Hotels-Beautiful-Year-Round-Lake-Home-Sleeps-8-Comfortably.h83708290.Hotel-Information) ![Holiday Stay in Madison – Warm & Cozy | Hunters Welcome!](https://images.trvl-media.com/lodging/121000000/120230000/120226900/120226875/4cf9f8a3_y.jpg) ### Holiday Stay in Madison – Warm & Cozy | Hunters Welcome! 10/10 Excellent "Beautiful home, very nicely decorated and super clean. We loved the king size bed and huge shower. The fenced in backyard was great for our two little dogs. The host is very accommodating and replied quickly to messages. I would definitely stay there again." [](https://expedia.ca/Madison-Hotels-Welcome-DSU-Madison-Athletics-Aviation-Students-Dg-Friendly.h120226875.Hotel-Information) ![Best Western Plus Lakeview Hotel](https://images.trvl-media.com/lodging/43000000/42650000/42640800/42640743/3d0a4089_y.jpg) ### Best Western Plus Lakeview Hotel 10/10 Excellent "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." [](https://expedia.ca/Madison-Hotels-Best-Western-Plus-Lakeview-Hotel.h42640743.Hotel-Information) ![Bilmar Inn & Suites by Hotel O Hwy 77](https://images.trvl-media.com/lodging/1000000/320000/317300/317203/8a4dbe1b_y.jpg) ### Bilmar Inn & Suites by Hotel O Hwy 77 10/10 Excellent "Room was clean and host very helpful!" [](https://expedia.ca/Sioux-Falls-Hotels-Bilmar-Inn-Suites-Dell-Rapids.h317203.Hotel-Information) ![AmericInn by Wyndham Hartford SD](https://images.trvl-media.com/lodging/10000000/9780000/9779900/9779853/cf46fc7d_y.jpg) ### AmericInn by Wyndham Hartford SD 10/10 Excellent "The breakfast was really very good. I should have given it a 5." [](https://expedia.ca/Sioux-Falls-Hotels-AmericInn-By-Wyndham-Hartford-SD.h9779853.Hotel-Information) ![Skeet's Retreat: Lake Herman's Hidden Gem of Adventure and Relaxation! Sleeps 8](https://images.trvl-media.com/lodging/104000000/103570000/103568500/103568434/26ce99bd_y.jpg) ### Skeet's Retreat: Lake Herman's Hidden Gem of Adventure and Relaxation! Sleeps 8 10/10 Excellent "Beautiful home and was perfect for a weekend getaway. " [](https://expedia.ca/Madison-Hotels-Skeets-Retreat-A-Hidden-Gem-Of-Adventure-And-Relaxation-On-Lake-Herman.h103568434.Hotel-Information) ![AmericInn by Wyndham Madison SD](https://images.trvl-media.com/lodging/23000000/22720000/22714700/22714648/1b5921ef_y.jpg) ### AmericInn by Wyndham Madison SD 10/10 Excellent "The hotel was great. Fast and friendly service at the front desk. Room was clean and spacious. Bathroom was spotless. Bed was a little hard for my liking. Easy access. Lots of places to park. Would stay again. " [](https://expedia.ca/Madison-Hotels-AmericInn-By-Wyndham-Madison-SD.h22714648.Hotel-Information) ![Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!](https://images.trvl-media.com/lodging/101000000/100940000/100931700/100931614/cb52a01f_y.jpg) ### Lakeside Getaway on Lake Madison. Hot tub with a view of the lake! 10/10 Excellent "Welcoming, responsive - easy to work with. Great place to stay! Thanks!" [](https://expedia.ca/Wentworth-Hotels-Lakeside-Getaway-On-Lake-Madison-Hot-Tub-With-A-View-Of-The-Lake.h100931614.Hotel-Information) ![Royal River Casino and Hotel](https://images.trvl-media.com/lodging/37000000/36830000/36825600/36825572/29914ffb_y.jpg) ### Royal River Casino and Hotel 10/10 Excellent "Hotel is clean, nice and quiet. The breakfast was delicious. " [](https://expedia.ca/Sioux-Falls-Hotels-Royal-River-Casino-And-Hotel.h36825572.Hotel-Information) ## More cheap stays in Chester ![Super 8 by Wyndham Madison](https://images.trvl-media.com/lodging/1000000/910000/908600/908526/47162c7b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Super 8 by Wyndham Madison 219 N Highland Ave Madison SD CA $91 CA $102 total Jan 30 - Jan 31 includes taxes & fees 6.4/10 (262 reviews) [](https://expedia.ca/Madison-Hotels-Super-8-By-Wyndham-Madison.h908526.Hotel-Information) ![AmericInn by Wyndham Madison SD](https://images.trvl-media.com/lodging/23000000/22720000/22714700/22714648/1b5921ef_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### AmericInn by Wyndham Madison SD 504 SE 10th St Madison SD CA $110 CA $122 total Jan 31 - Feb 1 includes taxes & fees 7.6/10 Good! (363 reviews) [](https://expedia.ca/Madison-Hotels-AmericInn-By-Wyndham-Madison-SD.h22714648.Hotel-Information) ![AmericInn by Wyndham Hartford SD](https://images.trvl-media.com/lodging/10000000/9780000/9779900/9779853/cf46fc7d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### AmericInn by Wyndham Hartford SD 1031 Diamond Circle Hartford SD CA $114 CA $124 total Feb 5 - Feb 6 includes taxes & fees 9/10 Wonderful! (788 reviews) [](https://expedia.ca/Sioux-Falls-Hotels-AmericInn-By-Wyndham-Hartford-SD.h9779853.Hotel-Information) ![Best Western Plus Lakeview Hotel](https://images.trvl-media.com/lodging/43000000/42650000/42640800/42640743/3d0a4089_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Plus Lakeview Hotel SE QUAD OF HWY 34 AND WASHINGTON AVE Madison SD CA $200 CA $220 total Feb 4 - Feb 5 includes taxes & fees 9.4/10 Exceptional! (228 reviews) [](https://expedia.ca/Madison-Hotels-Best-Western-Plus-Lakeview-Hotel.h42640743.Hotel-Information) ![Bilmar Inn & Suites by Hotel O Hwy 77](https://images.trvl-media.com/lodging/1000000/320000/317300/317203/8a4dbe1b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Bilmar Inn & Suites by Hotel O Hwy 77 510 N Highway 77 Dell Rapids SD [Get rates](https://expedia.ca/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=317203&PinnedHotelID=317203&HadPinnedHotel=true®ionId=553248635975872311) 6.8/10 (309 reviews) [](https://expedia.ca/Sioux-Falls-Hotels-Bilmar-Inn-Suites-Dell-Rapids.h317203.Hotel-Information) ## Hotels in Chester with star rating ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 2 properties [](https://expedia.ca/3Star-Chester-Hotels.s30-0-d553248635975872311.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 6 properties [](https://expedia.ca/2Star-Chester-Hotels.s20-0-d553248635975872311.Travel-Guide-Filter-Hotels) ## Frequently asked questions ### What is the best area to stay in Chester? > Chester is a very small town, and the main area of interest for visitors is centred around its few local businesses and the main roads that pass through it. You'll find most of what Chester has to offer along US Route 14 and South Dakota Highway 19\. This includes the local general store, a few eateries, and the post office. The town is very compact and walkable within this central area. > > > For travellers passing through or looking for a quiet stop, staying close to these main routes is the most convenient option. ### When is the best time to go to Chester? > Summer in Chester offers pleasant weather, with warm temperatures superb for enjoying outdoor activities. This period allows for comfortable exploration of the local area, including walks around Lake Vermillion and visits to nearby parks. It's also when many community events and festivals take place, providing a chance to experience local culture. Families often find this time ideal, as the weather is conducive to outdoor adventures and children are typically on holiday. > > > Early autumn in September also provides a lovely experience. The temperatures remain mild, and the changing colours of the leaves create a picturesque landscape, particularly around the lake. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Chester hotel booking with Expedia? ### How much is the nightly rate at a Chester hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Egan ](https://www.expedia.ca/4Star-Egan-Hotels.s40-0-d553248634983078381.Travel-Guide-Filter-Hotels) - [Baltic Hotels ](https://www.expedia.ca/Baltic-Hotels.d553248634983447400.Travel-Guide-Hotels) - [Lodges in Baltic ](https://www.expedia.ca/Baltic-Lodges.d553248634983447400-aaLodges.Travel-Guide-Accommodation) - [B&B in Colman ](https://www.expedia.ca/Colman-Bed-And-Breakfast.d3000353302-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Colman ](https://www.expedia.ca/Colman-Hotels-Cheap-Hotels.0-0-d3000353302-tCheapHotels.Travel-Guide-Filter-Hotels) - 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