Chepstow Vacation Packages

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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.
Charles Hope Apartments Swindon

Charles Hope Apartments Swindon

3.5 out of 5
Price was CA $1,170, price is now CA $1,052 per person
CA $1,052
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Bristol (BRS)
7.2/10 Good! (12 reviews)
Brilliant, I did leave a review on Google maps also. But I really enjoyed this stay. Me (m19) and my partner (F18) decided to go on a whim and book somewhere nice on Saturday night. It was a nice idea as we got out of her parents house. We really enjoyed our stay, the apartment was clean with a nice bathroom, kitchen, living area and bedroom. We cooked ourselves a meal and had a nice bath before heading out. It's literally on the doorstep of town so everything you need is within walking distance and there's also a washing machine and drying racks along with ironing boards and all that. I would definitely stay again. Only issue was parking as it's quite expensive. But there's a small parking lot opposite side of the street for £10 for 24 hours which is what I used. I definitely recommend. Check in was also really easy door codes worked with zero issues.

Reviewed on May 18, 2025

High Life Luxury Serviced Apartments

High Life Luxury Serviced Apartments

4 out of 5
Price was CA $1,688, price is now CA $1,488 per person
CA $1,488
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Bristol (BRS)
6/10 (3 reviews)
Hamilton Grace - The Quadrant

Hamilton Grace - The Quadrant

4 out of 5
Price was CA $1,429, price is now CA $1,318 per person
CA $1,318
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Bristol (BRS)
7.2/10 Good! (9 reviews)
De Vere Tortworth Court

De Vere Tortworth Court

4 out of 5
Price was CA $1,397, price is now CA $1,302 per person
CA $1,302
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bristol (BRS)
8.4/10 Very Good! (1,005 reviews)
We booked a room as part of a wedding party .wedding was at 2pm. Check in is 4pm which is quite late ,we had to be in the orangery for 4pm so staff managed to check us in 3.40pm .Room was perfect, slept well,breakfast amazing. Food at the wedding of Becky and Mark was incredible. Our first visit here and we will definitely return and use the pool/spa as we didn't get chance to on this occasion. Check out at 11am is good, no rushing around. Thankyou for a lovely stay

Reviewed on Aug. 11, 2025

Stanton House Hotel

Stanton House Hotel

3 out of 5
Price was CA $1,341, price is now CA $1,266 per person
CA $1,266
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Bristol (BRS)
8.6/10 Excellent! (554 reviews)
Beautiful building, in a superb location. Fitted perfectly our needs for visiting the nearby annual Royal International Airshow.

Reviewed on Jul. 29, 2025

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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 $142 per night from Sep 21 to Sep 22
CA $142
CA $170 total
Sep 21 - Sep 22
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Wonderful staff"

Reviewed on Aug. 17, 2025

Delta Hotels by Marriott St. Pierre Country Club
Celtic Manor Resort

Celtic Manor Resort

5 out of 5
Chepstow Road, Coldra Wood, Newport, Wales
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Sep 14 to Sep 15
CA $165
CA $199 total
Sep 14 - Sep 15
includes taxes & fees
8.2/10 Very Good! (1,307 reviews)
Catch up with a friend
"Thoroughly enjoyed catching up with a friend the food couldn’t be faulted. Very comfortable beds. The carpets need attention also bathrooms need a deep clean and dust the occasional table between the arm chairs in the bedroom."

Reviewed on Aug. 19, 2025

Celtic Manor Resort
Delta Hotels by Marriott Bristol City Centre

Delta Hotels by Marriott Bristol City Centre

4 out of 5
2 Lower Castle Street, Old Market, Bristol, England
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Aug 25 to Aug 26
CA $117
CA $140 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (376 reviews)
"Nice hotel. Next to the shopping centre. Lots of bus stops nearby. The bus stop opposite piccalino goes to the train station and takes 10 minutes. Lots of restaurants nearby. Room was comfortable and large. Good value for money. Area a bit dodgy at night. Reception staff really helpful and would ..."

Reviewed on Aug. 14, 2025

Delta Hotels by Marriott Bristol City Centre
See all 3,175 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

Discover the most popular places to visit in Chepstow

Millennium Stadium which includes modern architecture and a river or creek

Principality Stadium

Follow in the footsteps of sporting and musical greats when you tour this vast sporting arena. Walk on the pitch, see dressing rooms and lift a trophy.

Principality Stadium
Barry Island Beach

Barry Island Beach

If you’re looking for a quintessential Welsh seaside experience, look no further than Barry Beach in the picturesque Vale of Glamorgan.

Barry Island Beach
Cardiff Castle featuring château or palace, heritage architecture and heritage elements

Cardiff Castle

A fortified tower from the 12th century, World War II tunnels and Welsh military history make a fascinating day out at this magnificent castle.

Cardiff Castle

What to do in Chepstow

Cardiff: City Highlights Guided Walking Tour

Cardiff: City Highlights Guided Walking Tour

CA $32
per adult
Cardiff: City Highlights Guided Walking Tour
From Cardiff: Cliffs, Beaches And Castles Of South Wales

Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

CA $167
per adult
Cardiff: South Wales Cliffs, Beaches & Castles Day Tour
Cardiff Bay Boat Tour

Cardiff Bay Boat Tour

CA $24
per adult
74% of travellers recommend
Cardiff Bay Boat Tour
See all activities in Chepstow

Frequently asked questions

How much does a Chepstow vacation package cost?
Offering excellent value package deals from CA $1,052 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.