Chepstow Vacations from $1,016

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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.
High Life Luxury Serviced Apartments

High Life Luxury Serviced Apartments

4 out of 5
South Swindon
Price was $1,075, price is now $1,016 per person
$1,016
per person
Mar 19 - Mar 23
found 3 hours ago
Roundtrip flight included
Philadelphia (PHL) to Bristol (BRS)
6/10 (3 reviews)
Clayton Hotel Bristol City

Clayton Hotel Bristol City

4 out of 5
Bristol City Centre
Price was $1,236, price is now $1,120 per person
$1,120
per person
Mar 19 - Mar 23
found 3 hours ago
Roundtrip flight included
Philadelphia (PHL) to Bristol (BRS)
9.2/10 Wonderful! (1,095 reviews)
Good sized clean rooms with comfortable beds.

Reviewed on Jan 18, 2026

Best Western Plus Angel Hotel

Best Western Plus Angel Hotel

3 out of 5
Price was $1,121, price is now $1,030 per person
$1,030
per person
Mar 19 - Mar 23
found 3 hours ago
Roundtrip flight included
Philadelphia (PHL) to Bristol (BRS)
8.4/10 Very Good! (524 reviews)
Breakfast was great, the gym area needs to be assessed by health and safety.

Reviewed on Jan 8, 2026

Sidcot Arms

Sidcot Arms

3 out of 5
Sidcot
Price was $1,136, price is now $1,058 per person
$1,058
per person
Mar 19 - Mar 23
found 3 hours ago
Roundtrip flight included
Philadelphia (PHL) to Bristol (BRS)
9.2/10 Wonderful! (69 reviews)
A great stay. Staff friendly, room warm and clean

Reviewed on Jan 10, 2026

Bishopstrow Hotel & Spa

Bishopstrow Hotel & Spa

4 out of 5
Price was $1,785, price is now $1,688 per person
$1,688
per person
Mar 19 - Mar 23
found 3 hours ago
Roundtrip flight included
Philadelphia (PHL) to Bristol (BRS)
9/10 Wonderful! (330 reviews)
Suite had no study area / phone charging facilities. TV in the bedroom did not offer the services of the main Tv. No where to sit and prepare to fine. Coffee machine needed updating….drinks were only warm once poured. Bar area a little untidy and empty glasses were moved by us to make room to sit

Reviewed on Dec 21, 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
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 showing heritage elements, heritage architecture and a castle

Cardiff Castle

4.5/5(93 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

A tour arrives at Caerleon.

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

$121
per adult
The Wandering Bard's Valley Tour or the Swansea Bay Tour.
Cardiff: South Wales Cliffs, Bays & Castles Day Tour

Cardiff: South Wales Cliffs, Bays & Castles Day Tour

$112
per adult
Cardiff: South Wales Cliffs, Bays & Castles Day Tour
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

$112
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
$90 nightly
The price is $108 total per night from Feb 1 to Feb 2
$108 total
Feb 1 - Feb 2
Total with taxes and fees
8.2/10 Very Good! (1,009 reviews)
Great service and room

Reviewed on Jan 27, 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
$61 nightly
The price is $73 total per night from Feb 8 to Feb 9
$73 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (401 reviews)
Stay here a lot for work. Rooms are cozy, clean and modern. Beds super comfortable with plenty of pillows. Staff are really friendly.

Reviewed on Jan 23, 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
$97 nightly
The price is $117 total per night from Feb 1 to Feb 2
$117 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (1,196 reviews)
Room was very spacious, clean and well appointed. Will definitely stay here again.

Reviewed on Jan 26, 2026

Clayton Hotel Bristol City
See all 3,261 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 $1,016 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.