Chepstow Vacations from $892

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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.
OYO The Walnut Tree

OYO The Walnut Tree

$892
per person
Sep 29 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Bristol (BRS)
7/10 Good! (38 reviews)
Easy parking. Lovely staff. The room was really clean and comfortable. Check-in and out was very easy. Only thing we were unsure about is opening times for the restaurant were but other than that a really lovely stay and would come again.

Reviewed on Jul 26, 2026

The Lordleaze Hotel And Restaurant

The Lordleaze Hotel And Restaurant

$1,128
per person
Sep 29 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Bristol (BRS)
8.8/10 Excellent! (169 reviews)
Hawk House

Hawk House

$901
per person
Sep 29 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Bristol (BRS)
7.6/10 Good! (67 reviews)
I stayed at Hawk House for one night in Room 2, which had a comfortable double bed. The location was very convenient, particularly for getting on and off the motorway, so it was ideal for a quick stopover while travelling. The room was basic but had everything I needed for one night, including tea and coffee-making facilities, a small TV that worked well, and a small fan, which was very much appreciated in the heat. The shower was good and towels were provided, which was great. The only downside was that the area could be quite noisy, so I couldn’t really have the windows open, and you could hear some footsteps from the room above. However, this didn’t cause me any problems during the night. Overall, I found my stay pleasant. It was reasonably priced and perfectly suited to a one-night stop.

Reviewed on Aug 13, 2026

Derby Manor

Derby Manor

$1,413
per person
Sep 29 - Oct 5
found 3 hours ago
Roundtrip non-stop flight included
New York (JFK) to Bristol (BRS)
9.2/10 Wonderful! (655 reviews)
My husband and I arrived at Brooklyn house on Friday 24the July. We had approx 2.5hrs drive. There was no one on reception to check us in at approx 6pm. After ringing bell twice I finally tracked Maxine down who came to check us in. No eye contact was made between Maxine and my husband just me and she seemed quite 'cold'. She showed us to our room after going through everything and also asked what time we would like breakfast the following morning. We got to breakfast at 9am and again Maxine went through the process, told us to choose a table which was already set up and she would be over to take our breakfast order. We were left to our own devices and 40 mins later after hearing her greet other residents and asking them how their last evenings had been and serving other residents who had come in after us, I decided to get up and give her our breakfast order. No apology received by her. Although the breakfast was delicious, apart from the fact that my husband's scrambled eggs and salmon should have come with toast, we didn't even bother to mention. We both said we would never stay here again because of the unfriendly nature we had received on our check-in and breakfast. However, all was redeemed on our 2nd day this morning. Maxine was not there but we had the fortune of meeting Ana, a wonderful person who took our breakfast order which we received within 10mins of ordering, whilst helping ourselves to tea/coffee etc. Thank you Ana for your friendly warmth

Reviewed on Jul 26, 2026

Bournemouth Carlton Hotel By Sunday

Bournemouth Carlton Hotel By Sunday

Bournemouth City Centre
$1,222
per person
Sep 29 - Oct 5
found 3 hours ago
Roundtrip non-stop flight included
New York (JFK) to Bristol (BRS)
7.6/10 Good! (1,000 reviews)
For a 3 star hotel thought excellent. Room was large. Had comfy bed, very clean, tea and coffee supplied. Had a large bath and shower. Hotel was opposite the beach and had a lovely outside pool. Breakfast was buffet style. Had fresh fruit , yogurts, cereals. Cooked breakfast, toast. All hot and very nice.

Reviewed on Aug 11, 2026

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

Stay near popular Chepstow attractions

A historic stone cathedral with large arches and Gothic windows.

Tintern Abbey

9.6/10 (60 reviews)
Tour the ruins of an ancient monastery where Cistercian monks used to live, pray and study. See the remains of their former dwellings and church.
See properties
A historic stone building on a cliff overlooking a beach.
Photo by Miguel Vasquez

Chepstow Castle

9.0/10 (29 reviews)
Chepstow Castle is the oldest surviving stone fort in Britain and easily one of the most spectacular castles in Wales. The impressive castle dates back to the Norman invasion and perches precariously atop a cliff on the banks of the River Wye. Any visit is sure to invoke plenty of awe and wonder.
See properties

Chepstow Racecourse

9.0/10 (26 reviews)
Chepstow Racecourse is situated in Monmouthshire in south-east Wales, near the southern end of the Wye Valley. The track is a great point of interest in the UK and attracts visitors from all over the world.
See properties

St. Pierre Country Club

7.6/10 (17 reviews)
Enjoy a round of golf in Mathern at St. Pierre Country Club. Check out the shops and top-notch restaurants in this walkable area.
See properties

Symonds Yat Rock

9.6/10 (7 reviews)
Commune with nature and explore the great outdoors at Symonds Yat Rock during your travels in Tidenham. Make time for the spas and golf courses in this relaxing area.
See properties

Parva Farm Vineyard

10.0/10 (2 reviews)
You can enjoy a tasting or tour at Parva Farm Vineyard during your travels to Tintern. Check out the spas and top-notch restaurants in this relaxing area.
See properties

Caerwent Roman Town

6.0/10 (2 reviews)
You can learn about the history of Newport with a trip to Caerwent Roman Town. Make time for the spas and golf courses in this relaxing area.
See properties

Offa's Dyke National Trail - Southern Terminus

9.0/10 (7 reviews)
You can take time to visit Offa's Dyke National Trail - Southern Terminus during your travels to Tidenham.
See properties

What to do in Chepstow

From Barry Island: Gavin and Stacey Tour

From Barry Island: Gavin and Stacey Tour

$60
per adult
From Barry Island: Gavin and Stacey Tour
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day Tour

$113
per adult
Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day Tour
The Wandering Bard's Mythical West Wales Tour

The Wandering Bard's Mythical West Wales Tour

$114
per adult
100% of travellers recommend
The Wandering Bard's Mythical West Wales 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

St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
$111 nightly
$134 total
Aug 24 - Aug 25
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"Room stinks of damp, room was miles away from the restaurant. Food was average at best. Gym was shocking 2 weight benches and 6 people waiting for to use them. Not the worst hotel but certainly not worth the price"

Reviewed on Aug 12, 2026

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

Celtic Manor Resort

Chepstow Road Newport Wales
Fully refundableReserve now, pay when you stay
$122 nightly
$146 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (1,422 reviews)
"Everything was really awesome it's one of my favourite hotels"

Reviewed on Aug 13, 2026

Celtic Manor Resort
Clayton Hotel Bristol City

Clayton Hotel Bristol City

Broad Street Bristol England
Fully refundableReserve now, pay when you stay
$98 nightly
$117 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (1,430 reviews)
"Stylish and modern hotel, clean and tidy during my visit. My greeting by the reception staff was good and explained everything that i needed to know. Room was lovely, clean, comfortable and well maintained. If i was being picky, an extra chair would have been beneficial. Bar and restaurant were fab ..."

Reviewed on Aug 13, 2026

Clayton Hotel Bristol City
See all 3,831 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

Frequently asked questions

How much does a Chepstow vacation package cost?
Offering excellent value package deals from $892 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.