Chepstow Vacations from $943

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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.
Belvilla Newport City Centre Hotel - Lifestyle

Belvilla Newport City Centre Hotel - Lifestyle

3 out of 5
per person
Sep 22 - Sep 27
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Bristol (BRS)
7.8/10 Good! (303 reviews)
Great short stay, parking nearby on NCP Newport High Street. Short walk from shopping centre. Room did have burns in the carpet and bedding had eyeliner/mascara stains on arrival

Reviewed on Jun 30, 2025

Bishopstrow Hotel & Spa

Bishopstrow Hotel & Spa

4 out of 5
per person
Aug 31 - Sep 6
found 21 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Bristol (BRS)
9/10 Wonderful! (311 reviews)
You need a shop to sell the toiletries available for guests as well as local beers and ciders and cakes and biscuits. And perhaps links to local artists; prints make good souvenirs.

Reviewed on Jun 17, 2025

OYO the Regency, Clifton Bristol

OYO the Regency, Clifton Bristol

3.5 out of 5
Clifton
per person
Aug 31 - Sep 6
found 21 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Bristol (BRS)
7/10 Good! (809 reviews)
Was lookley roomwasnt a fan of the doors looking system alarms went off on more then. 1 occasion for me but other then that can't complain

Reviewed on Jun 11, 2025

The Old Bell Hotel

The Old Bell Hotel

4 out of 5
per person
Aug 31 - Sep 6
found 21 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Bristol (BRS)
9.4/10 Exceptional! (257 reviews)
Loved our stay at the Old Bell. Faultless. Super friendly staff, hotel, town and food perfect. Would go back tomorrow

Reviewed on Jun 20, 2025

Alison Court

Alison Court

3 out of 5
Clifton
per person
Aug 31 - Sep 6
found 21 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Bristol (BRS)
8.4/10 Very Good! (56 reviews)
The check in Apt and virtual key were unusual for me but the instructions were clear and easy to follow. The apartment was pristine and very inviting. I would recommend Alison Court to friends and family. I hope that on my next visit I am able to book for a longer stay.

Reviewed on Oct 13, 2023

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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 family-friendly 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: City Highlights Guided Walking Tour

Cardiff: City Highlights Guided Walking Tour

$23
per adult
Cardiff: City Highlights Guided Walking Tour
Cardiff Bay Boat Tour

Cardiff Bay Boat Tour

$17
per adult
74% of travellers recommend
Cardiff Bay Boat Tour
Cardiff: Waterfalls, Three Castles & Mountains Day Tour

Cardiff: Waterfalls, Three Castles & Mountains Day Tour

$122
per adult
Cardiff: Waterfalls, Three Castles & Mountains 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
$101 nightly
The price is $121 total per night from Jul 30 to Jul 31
$121 total
Jul 30 - Jul 31
Total includes taxes and fees
8.2/10 Very Good! (1,003 reviews)
Will definitely come back.
"Great stay. Very good service from all staff. Food could have been a bit better if I’m honest and was slightly overcooked. Not bad enough to put me off returning as it’s a lovely hotel in a nice setting. Showers could be a bit better as well."

Reviewed on Jun 28, 2025

Delta Hotels by Marriott St. Pierre Country Club
Aztec Hotel & Spa
Aztec Hotel & Spa
4 out of 5
Aztec West, Almondsbury, Bristol, England
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $115 total per night from Jul 20 to Jul 21
$115 total
Jul 20 - Jul 21
Total includes taxes and fees
8.6/10 Excellent! (1,000 reviews)
Refreshed and restored
"It was only one night but staying in a terraced room overlooking the lake we were fully refreshed for a full day ahead. Breakfast was excellent and my food allergies well catered for."

Reviewed on Jun 26, 2025

Aztec Hotel & Spa
Delta Hotels by Marriott Bristol City Centre
Delta Hotels by Marriott Bristol City Centre
4 out of 5
2 Lower Castle Street, Old Market, Bristol, England
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $103 total per night from Jul 6 to Jul 7
$103 total
Jul 6 - Jul 7
Total includes taxes and fees
8.6/10 Excellent! (327 reviews)
"Stay was lovely and the hotel was beautiful and clean"

Reviewed on Jun 29, 2025

Delta Hotels by Marriott Bristol City Centre
See all 3,187 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 $943 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.