Title: Chepstow Vacation Packages & Trips 2026  | Expedia.ca

[Chepstow Travel Guide](https://expedia.ca/Chepstow.dx6354154)[Hotels in Chepstow](https://expedia.ca/Chepstow-Hotels.d6354154.Travel-Guide-Hotels)[Vacation Rentals in Chepstow](https://expedia.ca/Chepstow-Vacation-Rentals.d6354154.Travel-Guide-VacationRentals)[Chepstow Car Rentals](https://expedia.ca/Car-Rentals-In-Chepstow.d6354154.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Chepstow Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

#### Your Chepstow Vacation

When you book a Chepstow vacation package, you can kick back and enjoy your getaway to the fullest. Discover the highlights of this unique city knowing that all your travel needs have been taken care of before you go. Ready to sightsee? Spend some time exploring major attractions such as [Walkerton Golf & Curling Club](https://www.expedia.ca/Walkerton-Golf-Curling-Club-Brockton.d553248621554118012.Vacation-Attraction) during your trip to Chepstow. Whatever your travel plans or budget, organizing a tailored Chepstow vacation is a cinch with Expedia.

## Ready to book your vacation to Chepstow?

Choose your dates

## Chepstow Hotel Deals

![SureStay Plus Hotel by Best Western Kincardine](https://images.trvl-media.com/lodging/1000000/70000/63800/63796/484edefe_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

SureStay Plus Hotel by Best Western Kincardine

791 Durham Street Kincardine ON

Fully refundableReserve now, pay when you stay

CA $116

CA $131 total

Jan 16 - Jan 17

includes taxes & fees

7.8/10 Good! (1,008 reviews)

All very good

Reviewed on Jan 4, 2026

[](https://expedia.ca/Hotel-Search?startDate=16%2F01%2F2026&endDate=17%2F01%2F2026&selected=63796&PinnedHotelID=63796&HadPinnedHotel=true&regionId=6354154)

![Best Western Plus Walkerton Hotel & Conference Centre](https://images.trvl-media.com/lodging/6000000/5060000/5058700/5058676/0adcc021_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Best Western Plus Walkerton Hotel & Conference Centre

10 East Ridge Road, Rural Route #2 Brockton ON

Fully refundableReserve now, pay when you stay

CA $160

CA $181 total

Feb 1 - Feb 2

includes taxes & fees

9.2/10 Wonderful! (665 reviews)

Breakfast is awesome and somebody makes you fresh eggs....cant beat it

Reviewed on Jan 10, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=5058676&PinnedHotelID=5058676&HadPinnedHotel=true&regionId=6354154)

![@HOME by Best Western Walkerton](https://images.trvl-media.com/lodging/114000000/113740000/113734700/113734624/w3837h2557x3y3-70b4fef0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

@HOME by Best Western Walkerton

37 Bruce Road 19 Walkerton ON

Fully refundableReserve now, pay when you stay

CA $179

CA $202 total

Jan 11 - Jan 12

includes taxes & fees

9.4/10 Exceptional! (25 reviews)

spotless, no pool or hot tub tho.

Reviewed on Nov 11, 2025

[](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=113734624&PinnedHotelID=113734624&HadPinnedHotel=true&regionId=6354154)

[See all 59 properties in Chepstow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&regionId=6354154)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Chepstow

#### Walkerton Golf & Curling Club

4.5/5(4 reviews)

Enjoy a round of golf in Walkerton at Walkerton Golf & Curling Club. Amble around the area's beaches or visit its casinos. 

[](https://expedia.ca/Walkerton-Golf-Curling-Club-Brockton.d553248621554118012.Vacation-Attraction)

## Explore a world of travel with Expedia

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\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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