Title: Chester Vacation Home Rentals from CA $121: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d553248635975872311.Travel-Guide-Hotels)[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) # Chester Vacation Rentals - ![](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 ## Check prices for these dates In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Chester ![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) ![Reception](https://images.trvl-media.com/lodging/10000000/9780000/9779900/9779853/9feef267.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 (780) "Great rooms, pool, breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate CA $115 CA $125 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Sioux-Falls-Hotels-AmericInn-By-Wyndham-Hartford-SD.h9779853.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) ![Bar (on property)](https://images.trvl-media.com/lodging/37000000/36830000/36825600/36825572/84b6b730.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 (569) "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](https://images.trvl-media.com/lodging/1000000/320000/317300/317203/4c21ed9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/320000/317300/317203/f7f34c7b.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 by Hotel O Hwy 77 [](https://www.expedia.ca/Sioux-Falls-Hotels-Bilmar-Inn-Suites-Dell-Rapids.h317203.Hotel-Information) Dell Rapids 7.0/10 Good (305) "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) ![Lobby lounge](https://images.trvl-media.com/lodging/43000000/42650000/42640800/42640743/0d87aea2.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) ![Lobby](https://images.trvl-media.com/lodging/43000000/42650000/42640800/42640743/9c03c40e.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) ### Best Western Plus Lakeview Hotel [](https://www.expedia.ca/Madison-Hotels-Best-Western-Plus-Lakeview-Hotel.h42640743.Hotel-Information) Madison 9.4/10 Exceptional (222) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wesley CA $175 CA $193 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Madison-Hotels-Best-Western-Plus-Lakeview-Hotel.h42640743.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/910000/908600/908526/63dec54e.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/fb6a9111.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) "nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Virginia CA $109 CA $121 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Madison-Hotels-Super-8-By-Wyndham-Madison.h908526.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) ![Property amenity](https://images.trvl-media.com/lodging/23000000/22720000/22714700/22714648/a3d5be32.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) ![Lobby](https://images.trvl-media.com/lodging/23000000/22720000/22714700/22714648/b7b6fdd1.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 (355) "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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Twila CA $123 CA $136 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Madison-Hotels-AmericInn-By-Wyndham-Madison-SD.h22714648.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=2025-12-28&endDate=2025-12-29®ionId=553248635975872311&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](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=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=VACATION_HOME) Condos [](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=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=CONDO) Cottages [](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=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=COTTAGE) ![](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-Private-Vacation-Homes.d553248635975872311-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Vacation-Homes.d553248635975872311-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![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) ![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 "Clean and friendly also just off interstate" [](https://expedia.ca/Sioux-Falls-Hotels-Bilmar-Inn-Suites-Dell-Rapids.h317203.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 "Very clean" [](https://expedia.ca/Madison-Hotels-Best-Western-Plus-Lakeview-Hotel.h42640743.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) ![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 "2nd stay here - great airport location. My only complaint is low pressure in shower. Quiet and comfy room. " [](https://expedia.ca/Sioux-Falls-Hotels-AmericInn-By-Wyndham-Hartford-SD.h9779853.Hotel-Information) ![WATERFRONT HOME ON LAKE MADISON](https://images.trvl-media.com/lodging/67000000/66290000/66285000/66284997/702e7dc1_y.jpg) ### WATERFRONT HOME ON LAKE MADISON 10/10 Excellent "The host was responsive and great! The house was very clean and comfortable. A great place to stay while in town for a tour of SDSU and the football game. It wasn't a bad drive to Brookings and nice to have room to hang out instead of a hotel. Would stay here again and highly recommend!" [](https://expedia.ca/Madison-Hotels-WATERFRONT-HOME-ON-LAKE-MADISON.h66284997.Hotel-Information) ![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 "Very clean, beautifully decorated and updated, well-maintained property. Sheets were soft and comfortable. One of the best properties we have stayed at! Although we only stayed a couple days, the home has everything you would need for a longer stay. All the comforts of home plus the great view! Had a beautiful sunrise!" [](https://expedia.ca/Madison-Hotels-Beautiful-Year-Round-Lake-Home-Sleeps-8-Comfortably.h83708290.Hotel-Information) ## Find out more about Chester ## Chester Vacation Homes information | Number of reviews | 2,491 | | ----------------- | ----------------- | | Accommodation | 10 Vacation Homes | | Lowest Price | CA $121 | | Highest Price | CA $193 | ## 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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