Chepstow Vacations from $1,684

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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.

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 $1,920, price is now $1,684 per person
$1,684
per person
May 28 - Jun 3
found 1 day ago
Roundtrip flight included
Albany (ALB) to Bristol (BRS)
7.8/10 Good! (1,008 reviews)
Bed was very uncomfortable, springs could be felt

Reviewed on Mar 23, 2026

Meridian Place - yourapartment

Meridian Place - yourapartment

4 out of 5
Clifton
Price was $2,871, price is now $2,475 per person
$2,475
per person
May 28 - Jun 3
found 1 day ago
Roundtrip flight included
Albany (ALB) to Bristol (BRS)
7/10 Good! (6 reviews)
It’s was Beautiful rooms was nice. Just a little ants in the kitchen and the bathroom other than even space for more than 8 people. Loved.

Reviewed on Apr 21, 2023

Bristol Marriott Royal Hotel

Bristol Marriott Royal Hotel

4 out of 5
Bristol Floating Harbour
Price was $2,141, price is now $1,879 per person
$1,879
per person
May 28 - Jun 3
found 1 day ago
Roundtrip flight included
Albany (ALB) to Bristol (BRS)
9.2/10 Wonderful! (1,249 reviews)
An amazing gluten free breakfast. Lovely lady stayed with us to go through options and we were not just handed an allergy file.

Reviewed on Mar 24, 2026

Redmayne House

Redmayne House

3.5 out of 5
Clifton
Price was $2,004, price is now $1,803 per person
$1,803
per person
May 28 - Jun 3
found 1 day ago
Roundtrip flight included
Albany (ALB) to Bristol (BRS)
9.4/10 Exceptional! (33 reviews)
Good location, modern furniture and top range appliances.

Reviewed on Feb 15, 2026

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Discover the most popular places to visit in Chepstow

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 relaxing area.

Cardiff Bay
Millennium Stadium showing 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
Cardiff Castle showing heritage elements, heritage architecture and a 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
$94 nightly
The price is $113 total per night from Apr 6 to Apr 7
$113 total
Apr 6 - Apr 7
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
Lovely to be pet friendly and have the ability to use the pool and the grounds. Great place to stay and would come again

Reviewed on Mar 23, 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
$85 nightly
The price is $102 total per night from Apr 6 to Apr 7
$102 total
Apr 6 - Apr 7
Total with taxes and fees
9.2/10 Wonderful! (420 reviews)
Yes it was a good place to stay

Reviewed on Mar 24, 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 Mar 29 to Mar 30
$90 total
Mar 29 - Mar 30
Total with taxes and fees
8.8/10 Excellent! (612 reviews)
Excellent in every way - great location, very handy car park!

Reviewed on Mar 25, 2026

Delta Hotels by Marriott Bristol City Centre
See all 3,351 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

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Frequently asked questions

How much does a Chepstow vacation package cost?
Offering excellent value package deals from $1,684 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.