Chepstow Vacations from $1,629

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Chepstow vacation packages

Price found within the past 48 hours. Click for updated prices.
Bristol Grand Hotel By Sunday

Bristol Grand Hotel By Sunday

4 out of 5
Bristol City Centre
Price was $1,747, price is now $1,629 per person
$1,629
per person
Jun 5 - Jun 9
found 3 hours ago
Roundtrip flight included
Houston (IAH) to Bristol (BRS)
7.8/10 Good! (1,006 reviews)
The hotel location was great the staff nice and the price fair. However when we stayed Easter weekend there was a celebration thing on. The sound check started just after 8am on the Sunday, it sounded like a full brass band accompanied by drums. Surely those not staying for this event could have been housed further from the noise. It was extremely loud and very disappointing. We got up dressed and left. I’ve never written a negative review before but the noise was something else it was happening right next next to our room.

Reviewed on Apr 7, 2026

2 Bedroom Farmhouse in Seend, No Deposit

2 Bedroom Farmhouse in Seend, No Deposit

2 out of 5
Price was $2,811, price is now $2,457 per person
$2,457
per person
May 24 - May 27
found 17 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Bristol (BRS)
No reviews
The Barleycorn

The Barleycorn

3 out of 5
Price was $3,812, price is now $3,407 per person
$3,407
per person
May 24 - May 27
found 17 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Bristol (BRS)
8.4/10 Very Good! (20 reviews)
Fab time, great food and very helpful we had a great stay

Reviewed on Aug 1, 2024

Salisbury Residences by Charles Hope

Salisbury Residences by Charles Hope

4 out of 5
Price was $2,674, price is now $2,436 per person
$2,436
per person
May 24 - May 27
found 17 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Bristol (BRS)
No reviews
Thornbury Castle, Relais & Châteaux

Thornbury Castle, Relais & Châteaux

4 out of 5
Price was $2,607, price is now $2,436 per person
$2,436
per person
Jun 5 - Jun 9
found 3 hours ago
Roundtrip flight included
Houston (IAH) to Bristol (BRS)
9.6/10 Exceptional! (637 reviews)
Great stay, lovely peaceful location. Evening meal was fantastic!

Reviewed on Apr 8, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chepstow
View all trips

Discover the most popular places to visit in Chepstow

Principality Stadium

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
Pierhead Building, a Grade One listed building of the National Assembly for Wales in Cardiff Bay, Wales. A Cardiff's landmark taken from Cardiff Bay.

Cardiff Bay

Explore the waterfront in Cardiff with a trip to Cardiff Bay. Discover the lively bars and acclaimed theater scene in this walkable area.

Cardiff Bay
Cardiff Castle

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: Gower Peninsula's Cliffs Scenic Day Tour

Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

$111
per adult
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour
Cardiff: South Wales Cliffs, Bays & Castles Day Tour

Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

$116
per adult
Cardiff: South Wales Cliffs, Beaches & Castles Day Tour
Cardiff: Waterfalls, Mountains & Castles Day Tour

Cardiff: Waterfalls, Mountains & Castles Day Tour

$116
per adult
100% of travellers recommend
Cardiff: Waterfalls, Mountains & Castles Day Tour
See all activities in Chepstow

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
$105 nightly
The price is $127 total per night from May 10 to May 11
$127 total
May 10 - May 11
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
Large upgraded room overlooking the lake, massive bed, bathroom a bit tired..great breakfast and amazing grounds and church

Reviewed on Apr 11, 2026

Delta Hotels by Marriott St. Pierre Country Club
Two Rivers, Chepstow by Marston’s Inns

Two Rivers, Chepstow by Marston’s Inns

4 out of 5
Newport Road Chepstow Wales
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $90 total per night from Apr 19 to Apr 20
$90 total
Apr 19 - Apr 20
Total with taxes and fees
9.2/10 Wonderful! (431 reviews)
Wasn’t expecting it to be as good as it was. Very comfortable bed, clean room and variety of teas. Very quiet too. Breakfast was lovely with lots of choice. Would highly recommend and stay again.

Reviewed on Apr 9, 2026

Two Rivers, Chepstow by Marston’s Inns
Delta Hotels by Marriott Bristol City Centre

Delta Hotels by Marriott Bristol City Centre

4 out of 5
2 Lower Castle Street Bristol England
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $90 total per night from Apr 26 to Apr 27
$90 total
Apr 26 - Apr 27
Total with taxes and fees
8.8/10 Excellent! (644 reviews)
Lovely big rooms, breakfast lovely, car park next door to hotel. Not far from shopping area and has lots of places to eat near by.

Reviewed on Apr 12, 2026

Delta Hotels by Marriott Bristol City Centre
See all 3,507 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.

Find the Best Chepstow Vacation Packages

Chepstow Essential Information

Language
Welsh
Currency
British pounds sterling
Population
16,200
Max Temp Winter
45ºF
Max Temp Summer
65ºF
Top Sights
Chepstow Castle, Chepstow Castle and Caldicot Castle

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chepstow vacation package cost?
Offering excellent value package deals from $1,629 on Expedia, you'll be thrilled with how little a vacation to Chepstow costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chepstow?
If you'd like to snag a cheap Chepstow vacation package, consider traveling in August, November and December. You'll usually find lower prices on accommodations and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Chepstow?
We recommend booking a Chepstow vacation for a minimum of 2 days. This will allow you enough time to check off major attractions such as Chepstow Museum and Parva Farm Vineyard, and also explore neighborhoods like Portskewett and Devauden. You might even be able to fit in a day trip (or two) from Chepstow.
Is it worth booking a vacation package to Chepstow?
From attractions such as Chepstow Racecourse and Chepstow Castle to its epic history, a Chepstow vacation offers a vibrant mix of experiences. With so much to do and see, it's time to find out for yourself why Chepstow is such a good vacation destination.
How to find the best Chepstow package deals?
Use Expedia's filters to help you find some unbeatable Chepstow package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Chepstow package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chepstow vacation as a package?
You can enjoy significant savings on your Chepstow escape by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chepstow?
If you're considering a spontaneous Chepstow getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Chepstow?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to escape to Chepstow.
  2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will probably be the biggest expense during your trip to Chepstow.
  3. Use Expedia's trip planning tool to explore Chepstow: Research every aspect of your trip to Chepstow with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how long to go for: Now that you're more familiar with Chepstow, you can work out the ideal length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Chepstow vacation package.
  6. Book experiences or activities in advance: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Chepstow. Find all the fun things to do in Chepstow with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Chepstow vacation packages?
Set off on your dream escape to Chepstow with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next payday — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up travel deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.