Chepstow Vacations from $1,570

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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 $1,606, price is now $1,570 per person
$1,570
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Bristol (BRS)
7.8/10 Good! (1,020 reviews)
Clean room amazing location onsite parking great bar and curtious staff would stay again

Reviewed on Nov 5, 2025

Belvilla Newport City Centre Hotel - Lifestyle

Belvilla Newport City Centre Hotel - Lifestyle

3 out of 5
Newport City Centre
Price was $1,661, price is now $1,610 per person
$1,610
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Bristol (BRS)
7.8/10 Good! (343 reviews)
Sheets hadn't been changed the whole time i was there. But everything else was good and clean. Didn't appreciate someone settling the smoke alarm off at 4am. good

Reviewed on Sep 28, 2025

Mad Swans in The Mendips

Mad Swans in The Mendips

3 out of 5
Price was $1,761, price is now $1,727 per person
$1,727
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Bristol (BRS)
No reviews
Higgihaus Cabot Mews Aparthotel

Higgihaus Cabot Mews Aparthotel

3.5 out of 5
Price was $1,681, price is now $1,650 per person
$1,650
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Bristol (BRS)
No reviews
Hotel du Vin & Bistro Bristol

Hotel du Vin & Bistro Bristol

4 out of 5
Price was $1,665, price is now $1,635 per person
$1,635
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Bristol (BRS)
9.4/10 Exceptional! (965 reviews)
A bit hot even with radiators off. But a lovely atmospheric room with subdued lighting, perfect for a romantic weekend.

Reviewed on Oct 19, 2025

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Discover the most popular places to visit in Chepstow

Millennium Stadium showing modern architecture and a river or creek

Principality Stadium

4/5(21 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
Wales Millennium Centre featuring a city, modern architecture and a square or plaza

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
Barry, South Wales. Vale of Glamorgan. UK

Barry Island Beach

4.5/5(4 reviews)

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

What to do in Chepstow

Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

Cardiff: South Wales Cliffs, Bays & Castles Day Tour

$120
per adult
Cardiff: South Wales Cliffs, Bays & Castles Day Tour
From Cardiff: Wye Valley and Brecon Beacons Full-Day Trip

From Cardiff: Wye Valley and Brecon Beacons Full-Day Trip

$133
per adult
100% of travellers recommend
From Cardiff: Wye Valley and Brecon Beacons Full-Day Trip
Cardiff: Waterfalls, Mountains & Castles Day Tour

Cardiff: Waterfalls, Mountains & Castles Day Tour

$120
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
$87 nightly
The price is $104 total per night from Nov 23 to Nov 24
$104 total
Nov 23 - Nov 24
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
clean , warm room , only snag was cars parked next to our windows and some noise due to being on ground floor

Reviewed on Nov 2, 2025

Delta Hotels by Marriott St. Pierre Country Club
Clayton Hotel Bristol City

Clayton Hotel Bristol City

4 out of 5
Broad Street, Bristol, England
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $93 total per night from Nov 23 to Nov 24
$93 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,082 reviews)
The hotel location was perfect for sightseeing. The room was furnished nicely.

Reviewed on Nov 6, 2025

Clayton Hotel Bristol City
Bristol Grand Hotel By Sunday

Bristol Grand Hotel By Sunday

4 out of 5
Broad Street, Bristol, England
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $81 total per night from Nov 30 to Dec 1
$81 total
Nov 30 - Dec 1
Total with taxes and fees
7.6/10 Good! (1,031 reviews)
Clean room amazing location onsite parking great bar and curtious staff would stay again

Reviewed on Nov 5, 2025

Bristol Grand Hotel By Sunday
See all 3,234 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 $1,570 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.