Chepstow Holidays

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    Save up to £335 when you book a flight and hotel together*
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    Packages with flights are ATOL protected

Your Chepstow Holiday

When you book a Chepstow holiday 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 during your trip to Chepstow. Whatever your travel plans or budget, organising a tailored Chepstow holiday is a cinch with Expedia.

Chepstow Essential Information

Language
English
Currency
Canadian dollars
Max Temp Winter
-3.89ºC
Max Temp Summer
21ºC
Top Sights
Walkerton Golf & Curling Club, Whispering Hills Golf Club and Brant Tract Trails Trailhead

Top hotels in Chepstow

The Chepstow Inn

The Chepstow Inn

3.5 out of 5
#2 Concession Road 6, Brockton, ON
The price is £153 per night from 10 Aug to 11 Aug
£153
10 Aug - 11 Aug
includes taxes & fees
9.6/10 Exceptional! (80 reviews)
"Amazing all around. Exactly what you hope to have in a B&B: excellent rooms (tastefully updated while maintaining all the original charm of the building), friendly and helpful host, lovely property and common spaces, and a great breakfast to start your day."

Reviewed on 4 Aug 2025

The Chepstow Inn
SureStay Plus Hotel by Best Western Kincardine

SureStay Plus Hotel by Best Western Kincardine

2.5 out of 5
791 Durham Street, Kincardine, ON
Fully refundableReserve now, pay when you stay
The price is £71 per night from 17 Aug to 18 Aug
£71
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (960 reviews)
"Breakfast was great"

Reviewed on 7 Aug 2025

SureStay Plus Hotel by Best Western Kincardine
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
2 MILLENNIUM WAY, Kincardine, ON
Fully refundableReserve now, pay when you stay
The price is £88 per night from 9 Sept to 10 Sept
£88
9 Sept - 10 Sept
includes taxes & fees
8/10 Very Good! (230 reviews)
"The room had stale air."

Reviewed on 4 Aug 2025

Comfort Inn & Suites
See all 64 properties in Chepstow
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chepstow travel package cost?
Starting from as low as , a package is your passport to inexpensive travel. Custom build your Chepstow trip by choosing from our wide range of hotels, airfares and rental cars.
If I'm not able to travel, can I cancel my Chepstow travel package?
If your travel plans in Chepstow have been upended, it's comforting to know that you can cancel your booking. If your booking was made in the last 24 hours, you may be able to get a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge fees. To learn more, check our Customer Service Portal.
How do I get a cheap travel package to Chepstow?
Imagine all the fabulous things you could do in Chepstow with extra cash in your pocket. Watch your savings stack up when you combine your flights and hotel into a Chepstow travel package. You have plenty of choice with Expedia too. In fact, you can take your pick of more than 550 airlines and 1,000,000 hotel options worldwide. Whether you're taking a break with the whole family or travelling on your own, planning a trip to Chepstow is better with a package.
Does Expedia offer Book Now, Pay Later Chepstow holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has worked out a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a fabulous getaway without drying up your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month works for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: Like the idea of paying for your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: When you see an incredible deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock it in.

What are the top hotels in Chepstow?
If it's your first visit to Chepstow, book a room at Best Western Plus Walkerton Hotel & Conference Centre or The Chepstow Inn. Both hotels offer comfy beds and are favourites among many savvy travellers.
How far in advance should I book my Chepstow holiday?
Reserving your seat early with Expedia means one less thing to worry about. Most carriers advertise prices up to 12 months in advance. This is generally the cheapest time to book. If circumstances have left you booking late, discount prices to Chepstow sometimes occur just a few weeks before departure.
What does an Expedia Chepstow travel package include?
Expedia has all you need to plan your Chepstow getaway, but what your package looks like is totally up to you. Pick from any combination of flights, hotels and rental cars. Searching for some activities to fill in your time? Once you've made your booking, you can add them too. No matter your style or budget, there's a travel package to match your needs.
What should I know before booking a Chepstow travel package?
A travel package can be easier on the hip pocket than individually booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and score impressive savings. No matter your holiday goals, you're sure to find a package that matches your budget.
Can I choose my airline with a Chepstow Expedia travel package?
Yes, and with over 550 airlines to choose from worldwide, you're spoiled for choice. Browse the available options and see which airline best suits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.