Chepstow Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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 a city break is calling, answer it with a vacation package to Chepstow. The neighborhood of Trellech United, which is great for culture, nature and history, makes a fantastic base for your adventures. If your trip to Chepstow includes some sightseeing, visit renowned attractions like Chepstow Racecourse, Tintern Abbey and Chepstow Castle. Expedia has what you need to escape your routine. Tailor your vacation to Chepstow to match your travel style, whatever that may look like.

Top Chepstow Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ibis Budget Newport

Ibis Budget Newport

3 out of 5
Price was CA $2,066, price is now CA $2,034 per person
CA $2,034
per person
Dec 27 - Dec 30
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bristol (BRS)
7.8/10 Good! (1,001 reviews)

Waterloo Hotel

Waterloo Hotel

3 out of 5
Pillgwenlly
Price was CA $2,100, price is now CA $2,062 per person
CA $2,062
per person
Dec 27 - Dec 30
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bristol (BRS)
10/10 Exceptional! (1 review)
Area good. Food ok room clean ok

Reviewed on Nov 5, 2026

Tŷ Newport

Tŷ Newport

4 out of 5
Langstone
Price was CA $2,197, price is now CA $2,167 per person
CA $2,167
per person
Dec 27 - Dec 30
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bristol (BRS)
9.4/10 Exceptional! (562 reviews)

The Newbridge Hotel

The Newbridge Hotel

2 out of 5
Newbridge
Price was CA $2,116, price is now CA $2,097 per person
CA $2,097
per person
Dec 27 - Dec 30
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bristol (BRS)
No reviews

Livin' Serviced Apartments - Newport

Livin' Serviced Apartments - Newport

2 out of 5
St Julians
Price was CA $2,133, price is now CA $2,120 per person
CA $2,120
per person
Dec 27 - Dec 30
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bristol (BRS)
No reviews
lovely appartment with kitchen facilities for a cup of tea, very comforatbke bed,good shower. excellent location - very central for the town, the river, the football ground.

Reviewed on Nov 5, 2026

Ready to book your vacation to Chepstow?

 

Choose your dates

Chepstow Hotel Deals

Delta Hotels by Marriott St. Pierre Country Club

Delta Hotels by Marriott St. Pierre Country Club

4 out of 5
St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Nov 12 to Nov 13
CA $146
CA $175 total
Nov 12 - Nov 13
includes taxes & fees
Delta Hotels by Marriott St. Pierre Country Club
Clayton Hotel Bristol City

Clayton Hotel Bristol City

4 out of 5
Broad Street Bristol England
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Nov 8 to Nov 9
CA $136
CA $163 total
Nov 8 - Nov 9
includes taxes & fees
Clayton Hotel Bristol City
Celtic Manor Resort

Celtic Manor Resort

5 out of 5
Chepstow Road Newport Wales
The price is CA $197 per night from Nov 27 to Nov 28
CA $197
CA $236 total
Nov 27 - Nov 28
includes taxes & fees
Celtic Manor Resort
See all 3,828 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Chepstow attractions

A historic stone cathedral with large arches and Gothic windows.

Tintern Abbey

9.6/10 (60 reviews)
Tour the ruins of an ancient monastery where Cistercian monks used to live, pray and study. See the remains of their former dwellings and church.
See properties

What to do in Chepstow

Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

CA $160
per adult
Cardiff: South Wales Cliffs, Beaches & Castles Day Tour
Cardiff/Swansea: Gower Peninsula's Cliffs & Mumbles Day Tour

Cardiff/Swansea: Gower Peninsula's Cliffs & Mumbles Day Tour

CA $160
per adult
100% of travellers recommend
Cardiff/Swansea: Gower Peninsula's Cliffs & Mumbles Day Tour
Caerphilly Castle

The Valleys tour or Swansea Bay tour. Please choose correctly.

CA $138
per adult
100% of travellers recommend
The Valleys tour or Swansea Bay tour. Please choose correctly.
See all activities in Chepstow

Frequently asked questions

How much does a Chepstow vacation package cost?
Offering excellent value package deals from CA $2,034 on Expedia, you'll be pleasantly surprised at how much a vacation to Chepstow costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chepstow?
Plan your trip for the off-peak season and you're likely to find cheap Chepstow vacation packages. Keep in mind that public holidays and major festivals and events can have an impact on prices, so do a little research before you go.
How many days is enough for Chepstow?
Chepstow vacations come in various shapes and sizes, but to really get a feel for this destination, we'd say 2 days is about right. With this timeframe, you can fit in top sights like Caldicot Castle and Symonds Yat Rock along with lesser-known spots. Don't forget to explore cool areas such as Portskewett and Devauden either. If you're smart with your time, you can even allow for a day trip or two from Chepstow too.
Is it worth booking a vacation package to Chepstow?
Known for its history and home to popular attractions like Chepstow Castle, a Chepstow vacation is sure to impress. Another top sight worth exploring? Don't miss Symonds Yat Rock.
How to find the best Chepstow package deals?
Landing a cheap Chepstow package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Chepstow package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chepstow vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Chepstow trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Chepstow?
If you're planning a spur-of-the-moment Chepstow vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chepstow?

  1. Choose when to travel: Check your diary and get packing. Your favourite time of year and the activities on offer will also help you decide when to escape to Chepstow.
  2. Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will likely be the biggest expense during your trip to Chepstow.
  3. Decide how many days away: Start by compiling a list of the sights and activities you'd like to experience in Chepstow. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Chepstow vacation package that brings all your bookings together.

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