Chepstow Vacations from $915

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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 $1,113, price is now $915 per person
$915
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
7.8/10 Good! (1,007 reviews)
Good location. Easy check in Rooms perfectly satisfactory (but a touch dated) Breakfast good It was hot weather during my stay but air conditioning was excellent

Reviewed on Aug 18, 2025

Montigo Resorts, Somerset

Montigo Resorts, Somerset

4 out of 5
Price was $1,258, price is now $1,020 per person
$1,020
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
8.4/10 Very Good! (315 reviews)
For a last minute replacement very nice, staff very frendly and easy to talk to.

Reviewed on Jun 2, 2025

Bristol Marriott Royal Hotel

Bristol Marriott Royal Hotel

4 out of 5
Bristol Floating Harbour
Price was $1,236, price is now $1,074 per person
$1,074
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
9.2/10 Wonderful! (1,131 reviews)
Much to like, but the accessible room was not terribly well designed for an elderly wheelchair user.

Reviewed on Aug 23, 2025

The Bristol Hotel

The Bristol Hotel

4 out of 5
Bristol City Centre
Price was $1,109, price is now $966 per person
$966
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
9/10 Wonderful! (1,009 reviews)
I liked the dining options, however, the housekeeping didn’t change my sheets throughout my 4 day stay. They only laid the bed with the same makeup-stained sheets I already had. Also, I noticed a food stain like a tomato sauce on the chair in my room upon arrival. Please pay more attention to deep cleaning.

Reviewed on Aug 24, 2025

Rowan Tree Your Apartment

Rowan Tree Your Apartment

4.5 out of 5
Cotham
Price was $1,232, price is now $1,081 per person
$1,081
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
8/10 Very Good! (5 reviews)
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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

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

Explore the waterfront in Cardiff with a trip to Cardiff Bay. Discover the top-notch restaurants and acclaimed theater scene in this relaxing area.

Cardiff Bay
Barry, South Wales. Vale of Glamorgan. UK

Barry Island Beach

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 Bay Boat Tour

Cardiff Bay Boat Tour

$17
per adult
74% of travellers recommend
Cardiff Bay Boat Tour
Cardiff: City Highlights Guided Walking Tour

Cardiff: City Highlights Guided Walking Tour

$23
per adult
Cardiff: City Highlights Guided Walking Tour
From Cardiff: Guided Tour of Welsh Valleys

From Cardiff: Guided Tour of Welsh Valleys

$121
per adult
100% of travellers recommend
From Cardiff: Guided Tour of Welsh Valleys
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
$89 nightly
The price is $107 total per night from Sep 21 to Sep 22
$107 total
Sep 21 - Sep 22
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
Top class
"Top class hotel . Enjoyed our stay from start to finish. Only downdide was water pressure in shower , could have been better ."

Reviewed on Aug 22, 2025

Delta Hotels by Marriott St. Pierre Country Club
Celtic Manor Resort

Celtic Manor Resort

5 out of 5
Chepstow Road, Coldra Wood, Newport, Wales
$108 nightly
The price is $130 total per night from Sep 1 to Sep 2
$130 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (1,303 reviews)
"Been staying here for decades. Property used to feel exclusive and high-end, with service unmatched even by American Ritz Carlton standards. In 2025, the resort has really gone towards the families, with children running throughout the resort, boisterous atmosphere at breakfast, and a feel of a mid-range ..."

Reviewed on Aug 21, 2025

Celtic Manor Resort
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
$85 nightly
The price is $101 total per night from Aug 31 to Sep 1
$101 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (379 reviews)
Excellent service
"Reception staff very helpful when my vehicle was to tall to fit in the car park, they came up with a solution straight away without me having to find an alternative."

Reviewed on Aug 21, 2025

Delta Hotels by Marriott Bristol City Centre
See all 3,175 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.

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Frequently asked questions

How much does a Chepstow vacation package cost?
Offering excellent value package deals from $915 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.