Chepstow Vacations from $1,054

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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.
Charles Hope Salisbury Centre

Charles Hope Salisbury Centre

3.5 out of 5
Price was $1,129, price is now $1,054 per person
$1,054
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Bristol (BRS)
9.4/10 Exceptional! (9 reviews)
Clean modern room, well equipped and great locaton

Reviewed on May 27, 2026

The Barleycorn

The Barleycorn

3 out of 5
Price was $2,152, price is now $1,902 per person
$1,902
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Bristol (BRS)
8.4/10 Very Good! (20 reviews)

Cwrt Bleddyn Hotel & Spa

Cwrt Bleddyn Hotel & Spa

3 out of 5
Llangybi
Price was $1,626, price is now $1,520 per person
$1,520
per person
Aug 24 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Bristol (BRS)
8.4/10 Very Good! (596 reviews)
Lovely stay

Reviewed on Jul 10, 2026

Quay Apartments Clarence House

Quay Apartments Clarence House

3.5 out of 5
St Julians
Price was $1,503, price is now $1,420 per person
$1,420
per person
Aug 24 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Bristol (BRS)
8.4/10 Very Good! (153 reviews)
Booked for 3 people and only had 1 King sized bed and you can open windows and the air on unit was only in the living room which made the bedroom unbearable hot. Wouldn’t stay here again

Reviewed on Jul 11, 2026

2Bd Garden Home - A Short Walk To Stonehenge

2Bd Garden Home - A Short Walk To Stonehenge

2 out of 5
Price was $1,278, price is now $1,209 per person
$1,209
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Bristol (BRS)
No reviews

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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

From Barry Island: Gavin and Stacey Tour

From Barry Island: Gavin and Stacey Tour

$60
per adult
From Barry Island: Gavin and Stacey Tour
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day Tour

$113
per adult
Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day Tour
Cardiff: South Wales Cliffs, Bays & Castles Day Tour

Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

$113
per adult
Cardiff: South Wales Cliffs, Beaches & 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 $125 total per night from Jul 26 to Jul 27
$125 total
Jul 26 - Jul 27
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
"Overall pretty great, but definitely a few negatives. Cleanliness was not 100%, by a long shot. Room was incredibly hot, oh so unbearably hot. We opened the sliding door as it was cool outside, but then flooded our room with bugs (100's of them). Room was close to the "lake", aka still water pond. ..."

Reviewed on Jul 13, 2026

Delta Hotels by Marriott St. Pierre Country Club
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
$67 nightly
The price is $80 total per night from Aug 2 to Aug 3
$80 total
Aug 2 - Aug 3
Total with taxes and fees
Delta Hotels by Marriott Bristol City Centre
Mollie's Bristol

Mollie's Bristol

4 out of 5
Cribbs Causeway Bristol England
$75 nightly
The price is $90 total per night from Aug 2 to Aug 3
$90 total
Aug 2 - Aug 3
Total with taxes and fees
Mollie's Bristol
See all 3,792 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 $1,054 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.