Chepstow Vacations from $1,327

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Shepherds Hut Near Exmoor National Park

Shepherds Hut Near Exmoor National Park

2.5 out of 5
Price was $1,564, price is now $1,327 per person
$1,327
per person
Apr 23 - Apr 29
found 1 day ago
Roundtrip flight included
Madison (MSN) to Bristol (BRS)
6.8/10 (5 reviews)
What a lovely stay! The place was quirky and surrounded by nature, peaceful and a great break from London. Our host was friendly and helpful. Would definitely go back.

Reviewed on Jul 28, 2021

Lucknam Park, Emblems Collection

Lucknam Park, Emblems Collection

5 out of 5
Price was $2,998, price is now $2,437 per person
$2,437
per person
Apr 23 - Apr 29
found 1 day ago
Roundtrip flight included
Madison (MSN) to Bristol (BRS)
9.6/10 Exceptional! (196 reviews)
We had a wonderful stay here with our son, both sets of grandparents, and our dog, and it was perfect for everyone. From the moment we arrived, the first impression was fantastic. The spa was lovely and a great place to relax, and the food was brilliant throughout our stay. Breakfast was delicious, although it did take a little while to arrive. The hotel is very family-friendly, with a lovely kids’ room and outdoor space that our little one really enjoyed. It’s also amazing for dogs, which made travelling with our pet so easy and enjoyable. We stayed in the 4-bedroom Grand Cottage, which was fantastic. Having private parking and easy access to all the facilities made everything very convenient. The staff were incredibly friendly and very accommodating, which made the whole experience even better. Overall, we had a fantastic stay and would highly recommend it.

Reviewed on Mar 9, 2026

The Lordleaze Hotel And Restaurant

The Lordleaze Hotel And Restaurant

3 out of 5
Price was $1,609, price is now $1,400 per person
$1,400
per person
Apr 23 - Apr 29
found 1 day ago
Roundtrip flight included
Madison (MSN) to Bristol (BRS)
8.8/10 Excellent! (152 reviews)
Great hotel, with professional , friendly and helpful staff Definitely recommend the hotel

Reviewed on Feb 11, 2026

Meridian Place - yourapartment

Meridian Place - yourapartment

4 out of 5
Clifton
Price was $2,763, price is now $2,448 per person
$2,448
per person
May 24 - May 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Bristol (BRS)
7/10 Good! (6 reviews)
It’s was Beautiful rooms was nice. Just a little ants in the kitchen and the bathroom other than even space for more than 8 people. Loved.

Reviewed on Apr 21, 2023

Clayton Hotel Bristol City

Clayton Hotel Bristol City

4 out of 5
Bristol City Centre
Price was $1,695, price is now $1,520 per person
$1,520
per person
Apr 23 - Apr 29
found 1 day ago
Roundtrip flight included
Madison (MSN) to Bristol (BRS)
9.2/10 Wonderful! (1,233 reviews)
Good basic clean hotel

Reviewed on Mar 17, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chepstow
View all trips

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(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

Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

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

Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

$119
per adult
Cardiff: South Wales Cliffs, Beaches & Castles Day Tour
The Royal Mint Experience: Ticket, Guided Tour & Exhibition

The Royal Mint Experience: Ticket, Guided Tour & Exhibition

$24
per adult
100% of travellers recommend
The Royal Mint Experience: Ticket, Guided Tour & Exhibition
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 Mar 23 to Mar 24
$106 total
Mar 23 - Mar 24
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Lovely stay

Reviewed on Mar 19, 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
$70 nightly
The price is $84 total per night from Mar 22 to Mar 23
$84 total
Mar 22 - Mar 23
Total with taxes and fees
9.2/10 Wonderful! (418 reviews)
It was pretty quiet considering the location. I was allocated an accessible room which I didn’t book - they tend to make me feel uncomfortable or sick.

Reviewed on Mar 19, 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 Mar 22 to Mar 23
$89 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (606 reviews)
Excellent value for money

Reviewed on Mar 19, 2026

Delta Hotels by Marriott Bristol City Centre
See all 3,338 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chepstow vacation package cost?
Offering excellent value package deals from $1,327 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.