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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 $975, price is now $905 per person
$905
per person
May 2 - May 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Bristol (BRS)
7.8/10 Good! (1,008 reviews)
Would not say it was worth the price looks to be an old school repurposed. Beds are not comfortable very springy. And layout was odd, not even a mini fridge in the room, TV was useless not able to play Netflix or YouTube nothing

Reviewed on Mar 29, 2026

Belvilla Newport City Centre Hotel - Lifestyle

Belvilla Newport City Centre Hotel - Lifestyle

3 out of 5
Newport City Centre
Price was $2,158, price is now $1,927 per person
$1,927
per person
Jun 22 - Jun 27
found 13 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Bristol (BRS)
7.8/10 Good! (358 reviews)
The room was spacious and clean . comfortable bed with everything we needed. Staff were friendly and let us check in early. Location was excellent, right in the heart on the centre.

Reviewed on Feb 22, 2026

The Royal George

The Royal George

2.5 out of 5
Price was $2,602, price is now $2,378 per person
$2,378
per person
Jun 22 - Jun 27
found 13 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Bristol (BRS)
9.8/10 Exceptional! (6 reviews)
Really lovely property- will be coming back. Recommend it completely

Reviewed on Mar 12, 2026

The Priory Hotel and Restaurant

The Priory Hotel and Restaurant

4 out of 5
Caerleon
Price was $2,161, price is now $2,005 per person
$2,005
per person
Jun 22 - Jun 27
found 13 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Bristol (BRS)
9.2/10 Wonderful! (668 reviews)
Staff were wonderful!

Reviewed on Feb 28, 2026

Holiday Inn NEWPORT by IHG

Holiday Inn NEWPORT by IHG

3 out of 5
Ringland
Price was $2,084, price is now $1,951 per person
$1,951
per person
Jun 22 - Jun 27
found 13 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Bristol (BRS)
8/10 Very Good! (478 reviews)
Booked a premium room for myself, partner and toddler. As always room was clean and up to standard. Unfortunately the wifi was not working, so the receptionist quickly switched rooms for us. Unfortunately again wifi was not working and the AC was stuck on cold setting. Mentioned again at the front desk, to which receptionist explained they are getting new wifi and was very apologetic. Third time lucky, we was placed in a standard room, where the wifi and AC was working fine. Staff did note down and mention because we ended up staying in a standard and not premium like booked, they would give a discount for a future booking and meal vouchers. Overall service and staff was very good- we have stayed at this same hotel 4 times previously, so although this time wasn’t our usual excellent stay, it won’t put us off returning.

Reviewed on Dec 26, 2025

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Discover the most popular places to visit in Chepstow

Principality Stadium

Principality Stadium

4/5(22 reviews)

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

4.5/5(26 reviews)

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
Cardiff Castle

Cardiff Castle

4.5/5(94 reviews)

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

From Barry Island: Gavin and Stacey Tour

From Barry Island: Gavin and Stacey Tour

$60
per adult
From Barry Island: Gavin and Stacey Tour
The Wandering Bard's Valley Tour or the Swansea Bay Tour.

The Wandering Bard's Valley Tour or the Swansea Bay Tour.

$119
per adult
The Wandering Bard's Valley Tour or the Swansea Bay Tour.
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
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
$98 nightly
The price is $118 total per night from Apr 6 to Apr 7
$118 total
Apr 6 - Apr 7
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
The leisure facilities are not good enough for the size of the hotel. Everything is so small, the pool and the jacuzzi. The sauna and steam room were cozy when more than 4 people wanted to use. Needs much better leisure facilities. We left after 15 minutes as we were just sat round waiting to ...

Reviewed on Mar 28, 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
$76 nightly
The price is $91 total per night from Apr 6 to Apr 7
$91 total
Apr 6 - Apr 7
Total with taxes and fees
9.2/10 Wonderful! (422 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
$74 nightly
The price is $89 total per night from Apr 6 to Apr 7
$89 total
Apr 6 - Apr 7
Total with taxes and fees
8.8/10 Excellent! (621 reviews)
Good selection of food at breakfast. Hotel in good location to reach attractions by foot. However, hotel located by a busy road & noisy with sirens on a night.

Reviewed on Mar 30, 2026

Delta Hotels by Marriott Bristol City Centre
See all 3,395 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 $905 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.