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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 City Stays

Bristol City Stays

3.5 out of 5
Saint Paul's
Price was $1,154, price is now $1,029 per person
$1,029
per person
Mar 7 - Mar 12
found 14 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Bristol (BRS)
9.4/10 Exceptional! (39 reviews)
Clean, super close to the shops, very pleased 😌

Reviewed on Oct 29, 2025

Bristol Marriott Royal Hotel

Bristol Marriott Royal Hotel

4 out of 5
Bristol Floating Harbour
Price was $1,423, price is now $1,214 per person
$1,214
per person
Mar 7 - Mar 12
found 14 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Bristol (BRS)
9.2/10 Wonderful! (1,190 reviews)
Location perfect for overnight stay in Bristol. Close to plenty of food options and walking trails in the morning. We took advantage of the onsite restaurant for dinner which was a great experience for both setting, food and wine options. Recommend the 28oz shared platter for two which was plentiful.

Reviewed on Jan 10, 2026

Belvilla Newport City Centre Hotel - Lifestyle

Belvilla Newport City Centre Hotel - Lifestyle

3 out of 5
Newport City Centre
Price was $1,215, price is now $1,058 per person
$1,058
per person
Mar 7 - Mar 12
found 14 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Bristol (BRS)
7.8/10 Good! (346 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

Bristol Grand Hotel By Sunday

Bristol Grand Hotel By Sunday

4 out of 5
Bristol City Centre
Price was $1,227, price is now $1,075 per person
$1,075
per person
Mar 7 - Mar 12
found 14 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Bristol (BRS)
7.8/10 Good! (1,000 reviews)
Great location for exploring the city , room was clean and warm (good heating). Bed comfortable. Walls paper thin tho , so had to listen to some party goers loud conversations at 3am. But we were there early Dec when the Christmas parties had kicked off, so bound to happen. Hotel Staff were friendly and helpful. The bar service was good, some lovely cocktails created. Also had a meal in the Restaurant there and food was delicious and the restaurant team were lovely . Great stay, would stay there again. PS: Car park to the side of the hotel and had plenty of spaces.

Reviewed on Jan 1, 2026

DoubleTree by Hilton Hotel Bristol South - Cadbury House

DoubleTree by Hilton Hotel Bristol South - Cadbury House

4 out of 5
Price was $1,222, price is now $1,071 per person
$1,071
per person
Mar 7 - Mar 12
found 14 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Bristol (BRS)
8.2/10 Very Good! (1,001 reviews)
Clean spacious rooms, fab bath tub, good plentyful breakfast, beds are firm. Check in staff needed to be more informative, restaurant staff very helpful

Reviewed on Jan 2, 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: South Wales Cliffs, Beaches & Castles Day Tour

Cardiff: South Wales Cliffs, Bays & Castles Day Tour

$119
per adult
Cardiff: South Wales Cliffs, Bays & Castles Day Tour
Cardiff: Gower Peninsula's Cliffs & Bays Scenic Day Tour

Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

$119
per adult
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour
From Cardiff: Guided Hike to 8 Waterfalls in Brecon Beacons

From Cardiff: Guided Hike to 8 Waterfalls in Brecon Beacons

$91
per adult
From Cardiff: Guided Hike to 8 Waterfalls in Brecon Beacons
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
$88 nightly
The price is $106 total per night from Jan 18 to Jan 19
$106 total
Jan 18 - Jan 19
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
Staff were so friendly and reassuring, extremely helpful and professional such an asset to the hotel. Thank you for an enjoyable stay.

Reviewed on Jan 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
$60 nightly
The price is $72 total per night from Jan 22 to Jan 23
$72 total
Jan 22 - Jan 23
Total with taxes and fees
9/10 Wonderful! (398 reviews)
Easy check in with pleasant staff. Room was clean, tidy and spacious. This is a pretty new building by the look of it! Room was nice and warm (especially nice as it was a very cold day). Bed was comfortable with clean and high quality linen. Bathroom super clean with plenty of hot, high pressure ...

Reviewed on Jan 5, 2026

Two Rivers, Chepstow by Marston’s Inns
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 Jan 18 to Jan 19
$93 total
Jan 18 - Jan 19
Total with taxes and fees
9/10 Wonderful! (1,183 reviews)
It's a lovely hotel in great location. Clean spacious room, comfortable bed and amazingly quiet!

Reviewed on Jan 11, 2026

Clayton Hotel Bristol City
See all 3,283 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 $1,029 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.