Title: Chester Vacation Rentals : Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Chester](https://expedia.ca/Chester-Hotels.d553248635975872311.Travel-Guide-Hotels)[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)

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## Check prices for these dates

In two weeks

[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 two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=553248635975872311&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

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## Find vacation rentals that suit your style

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+South+Dakota%2C+United+States+of+America&regionId=553248635975872311&latLong=43.894913%2C-96.92656&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+South+Dakota%2C+United+States+of+America&regionId=553248635975872311&latLong=43.894913%2C-96.92656&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+South+Dakota%2C+United+States+of+America&regionId=553248635975872311&latLong=43.894913%2C-96.92656&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VACATION_HOME)

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## Top Chester Hotel Reviews

![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

"Clean room, quiet hotel"

[](https://expedia.ca/Madison-Hotels-AmericInn-By-Wyndham-Madison-SD.h22714648.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 what we needed. Staff, amenities, and help with requests were amazing as usual."

[](https://expedia.ca/Madison-Hotels-Best-Western-Plus-Lakeview-Hotel.h42640743.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

"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)

![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)

![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)

## Find out more about Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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## Frequently asked questions

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