Title: Chester Vacation Rentals from CA $339: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Chester](https://expedia.ca/Chester-Hotels.d553248635975478048.Travel-Guide-Hotels)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d553248635975478048.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d553248635975478048.Destination-Travel-Guides)

![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?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

## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975478048&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=553248635975478048&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=553248635975478048&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=553248635975478048&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)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

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

[Book now](https://expedia.ca/deals?rfrr=VR_SPRING_PROMO_553248635975478048)

## Find vacation rentals that suit your style

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Oklahoma%2C+United+States+of+America&regionId=553248635975478048&latLong=36.216428%2C-98.920928&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VILLA)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Oklahoma%2C+United+States+of+America&regionId=553248635975478048&latLong=36.216428%2C-98.920928&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VACATION_HOME)

![](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-Vacation-Rentals.d553248635975478048.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Vacation-Rentals.d553248635975478048.Travel-Guide-VacationRentals)

## Top Chester Hotel Reviews

![Best Western Plus Fairview Inn & Suites](https://images.trvl-media.com/lodging/13000000/12510000/12501900/12501865/cbafc8ae_y.jpg)

### Best Western Plus Fairview Inn & Suites

10/10 Excellent

"The breakfast was great and rooms were clean. The gentleman that checked us in was super friendly!!"

[](https://expedia.ca/Fairview-Hotels-Best-Western-Plus-Fairview-Inn-Suites.h12501865.Hotel-Information)

![Casual Comfort for Duners, Hunters, and Normal Folks](https://images.trvl-media.com/lodging/79000000/78470000/78463100/78463078/ddd84d51_y.jpg)

### Casual Comfort for Duners, Hunters, and Normal Folks

10/10 Excellent

"Very impressive with the attention to detail in decor , well stocked and clean"

[](https://expedia.ca/Waynoka-Hotels-Casual-Comfort-For-Duners.h78463078.Hotel-Information)

![Just Dune It - West](https://images.trvl-media.com/lodging/77000000/76640000/76636100/76636020/ec5e3f31_y.jpg)

### Just Dune It - West

10/10 Excellent

"I’m looking forward to coming back here many of times. This is a perfect place for a family to stay."

[](https://expedia.ca/Waynoka-Hotels-Family-Setting-On-Dune-Trail-24-Access.h76636020.Hotel-Information)

![COZY CANTON GETAWAY 3 Bedroom/2 Bath Near Canton Lake With Extra Parking!](https://images.trvl-media.com/lodging/118000000/117470000/117464100/117464065/01d33ea3_y.jpg)

### COZY CANTON GETAWAY 3 Bedroom/2 Bath Near Canton Lake With Extra Parking!

10/10 Excellent

"Very clean and cozy! Great location would definitely stay there again!"

[](https://expedia.ca/Canton-Hotels-COZY-CANTON-GETAWAY-3-Bedroom2-Bath-Near-Canton-Lake-With-Extra-Parking.h117464065.Hotel-Information)

![Just Dune It - East](https://images.trvl-media.com/lodging/77000000/76740000/76739400/76739330/c375743f_y.jpg)

### Just Dune It - East

10/10 Excellent

"A great place to stay. We rented both homes for a family trip. Easy access to the sand trail without having to drive the paddle tires on asphalt. "

[](https://expedia.ca/Waynoka-Hotels-Family-Friendly-Site-With-24-Hour-Access-To-Dunes.h76739330.Hotel-Information)

![The Ash Street Stables Villas](https://images.trvl-media.com/lodging/71000000/70760000/70759700/70759632/85513693_y.jpg)

### The Ash Street Stables Villas

10/10 Excellent

"Everything was beyond perfect here!"

[](https://expedia.ca/Waynoka-Hotels-The-Ash-Street-Stables-Villas.h70759632.Hotel-Information)

![Escape to Waynoka: Your Ultimate 4-Bedroom Retreat Near Little Sahara State Park](https://images.trvl-media.com/lodging/105000000/104440000/104438400/104438364/e0f7239d_y.jpg)

### Escape to Waynoka: Your Ultimate 4-Bedroom Retreat Near Little Sahara State Park

10/10 Excellent

"Host very attentive to their guest. Very cute little place stay. Location is perfect. Dollar general a block away and perfect location to the sand dunes not to close and not to far away. In general it was a very great experience. Not one complaint. If you are coming In for hunting this is a perfect place for you. Coming from a family of lots hunters, this would be the place to stay."

[](https://expedia.ca/Waynoka-Hotels-Escape-To-Waynoka-Your-Ultimate-4-Bedroom-Retreat-Near-Little-Sahara-State-Park.h104438364.Hotel-Information)

![Nancy Mae’s Cottage your home away from home, it’s all you need. Sleeps 6. ](https://images.trvl-media.com/lodging/84000000/83320000/83318000/83317984/e82bf38b_y.jpg)

### Nancy Mae’s Cottage your home away from home, it’s all you need. Sleeps 6\. 

10/10 Excellent

"House was very clean. Mattress excellent in both rooms. Everything was great, except TV, no cable, have to have Roku…couldn’t watch football."

[](https://expedia.ca/Waynoka-Hotels-Nancy-Maes-Cottage-Your-Home-Away-From-Home.h83317984.Hotel-Information)

![The Ash Street Stables Villas](https://images.trvl-media.com/lodging/71000000/70770000/70762700/70762619/1a2cf9f4_y.jpg)

### The Ash Street Stables Villas

10/10 Excellent

"Clean, easy communication. "

[](https://expedia.ca/Waynoka-Hotels-Villa.h70762619.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.   

## Explore a world of travel with Expedia

- Trending destinations on Expedia.ca
- All accommodation types in Chester

### Trending destinations on Expedia.ca

- [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
- [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals)
- [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals)
- [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals)
- [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals)
- [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations)
- [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals)
- [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals)
- [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals)
- [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals)
- [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals)
- [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals)
- [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals)
- [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals)
- [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
- [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Chester ](https://expedia.ca/Chester-Private-Vacation-Homes.d553248635975478048-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Villas in Chester ](https://expedia.ca/Chester-Villas.d553248635975478048-aaVillas.Travel-Guide-Accommodation)
- [Motels in Chester ](https://expedia.ca/Chester-Motels.d553248635975478048-aaMotels.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Chester?

### What are some of the best vacation rentals that Chester has to offer?

### What are vacation rentals like in Chester?

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app