Title: Chepstow Vacation Packages 2026 from $1,288 | Expedia.com

[Chepstow Travel Guide](https://expedia.com/Chepstow.dx5618)[Hotels in Chepstow](https://expedia.com/Chepstow-Hotels.d5618.Travel-Guide-Hotels)[Vacation Rentals in Chepstow](https://expedia.com/Chepstow-Vacation-Rentals.d5618.Travel-Guide-VacationRentals)[Flights to Chepstow](https://expedia.com/Cheap-Flights-To-Chepstow.d5618.Travel-Guide-Flights)[Things to do in Chepstow](https://expedia.com/Things-To-Do-In-Chepstow.d5618.Travel-Guide-Activities)[Car Rentals in Chepstow](https://expedia.com/Car-Rentals-In-Chepstow.d5618.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6086409/fb8b13ac-189c-4b6e-a910-25ac56c540ec.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Chepstow Vacations from $1,288

## Book a Hotel + Flight or Car together to unlock savings

## 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](https://www.expedia.com/Chepstow-Racecourse-Cardiff.d6171652.Vacation-Attraction), [Tintern Abbey](https://www.expedia.com/Tintern-Abbey-Cardiff.d6086409.Vacation-Attraction) and [Chepstow Castle](https://www.expedia.com/Chepstow-Castle-Cardiff.d6086505.Vacation-Attraction). 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 Marriott Royal Hotel](https://images.trvl-media.com/lodging/1000000/540000/536600/536507/13e93bdf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bristol Marriott Royal Hotel

Bristol Floating Harbour

$1,288

per person

Apr 1 - Apr 6

found 7 hours ago

Roundtrip flight included

Philadelphia (PHL) to Bristol (BRS)

9.2/10 Wonderful! (1,190 reviews)

Need to upgrade to USB C in the lights not the old USB

Reviewed on Feb 16, 2026

![Montigo Resorts, Somerset](https://images.trvl-media.com/lodging/1000000/520000/517300/517268/ccaa6300_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Montigo Resorts, Somerset

$1,295

per person

May 9 - May 15

found 16 hours ago

Roundtrip non-stop flight included

Phoenix (PHX) to Bristol (BRS)

8.4/10 Very Good! (325 reviews)

Spa facilities are very small but the treatments are excellent. Food is abysmal, disappointing and overpriced. Bar is limited with few non alcoholic options and appalling non alcoholic cocktails. All the staff are friendly and helpful but have their work cut out for them in a tired hotel past its best. There are signs of half-completed basic renovations and worn, tired carpets. Lovely gardens.

Reviewed on Dec 24, 2025

![The Old Bell Hotel](https://images.trvl-media.com/lodging/23000000/22720000/22711000/22710966/210c50b3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Old Bell Hotel

$1,464

per person

Apr 26 - May 2

found 16 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Bristol (BRS)

9.4/10 Exceptional! (274 reviews)

The town house was lovely, however the staff were dismissive to the point of being rude when we checked in. The guy who took my card and showed us to our townhouse literally couldn’t be bothered to smile or make any effort at all. We paid a lot of money for my partners birthday and he opened the door handed over the key and left. We had no idea how to use anything barely slept because we couldn’t turn the heating off. So disappointed. However when we went for supper in the restaurant we had a lovely young waitress who was engaging, courteous and attentive. When we checked out again the lady on the desk wasn’t interested in our complaint of the heating and barely smiled. Such a shame for such a lovely place to be let down by some of its staff.

Reviewed on Feb 6, 2026

![Rowan Tree Your Apartment](https://images.trvl-media.com/lodging/38000000/37030000/37020300/37020256/5f73a80c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Rowan Tree Your Apartment

Cotham

$1,487

per person

Apr 1 - Apr 6

found 7 hours ago

Roundtrip flight included

Philadelphia (PHL) to Bristol (BRS)

8/10 Very Good! (5 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Chepstow

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-16/2026-03-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BRS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_5618)

### Discover the most popular places to visit in Chepstow

![Millennium Stadium showing modern architecture and a river or creek](https://images.trvl-media.com/place/6084257/e0623f37-090c-417c-b9a3-3ceea290b34c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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.

[](https://expedia.com/Principality-Stadium-Cardiff-City-Centre.d6084257.Vacation-Attraction)

![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.](https://images.trvl-media.com/place/553248621532490507/5dbf41fb-82e5-44f5-94c4-a1963ca618dd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Cardiff Bay

Explore the waterfront in Cardiff with a trip to Cardiff Bay. Discover the lively bars and acclaimed theater scene in this family-friendly area. 

[](https://expedia.com/Cardiff-Bay-Butetown.d553248621532490507.Vacation-Attraction)

![Cardiff Castle showing heritage elements, heritage architecture and a castle](https://images.trvl-media.com/place/6084239/ed41c62f-a193-4860-b2b1-e025766c3f02.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Cardiff Castle

A fortified tower from the 12th century, World War II tunnels and Welsh military history make a fascinating day out at this magnificent castle.

[](https://expedia.com/Cardiff-Castle-Cardiff-City-Centre.d6084239.Vacation-Attraction)

### What to do in Chepstow

![Cardiff: South Wales Cliffs, Bays & Castles Day Tour](https://mediaim.expedia.com/localexpert/49610322/fc887d1b-1935-4547-8fbb-fa2e1453cb38.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

$120

per adult

[](https://expedia.com/things-to-do/cardiff-south-wales-cliffs.a49610322.activity-details)

![Cardiff: Gower Peninsula's Cliffs Scenic Day Tour](https://mediaim.expedia.com/localexpert/49556120/2ed2191f-1f28-407b-b6ce-a614604a299d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

$120

per adult

[](https://expedia.com/things-to-do/cardiff-gower-peninsulas-cliffs-scenic-day-tour.a49556120.activity-details)

![The Royal Mint Experience: Ticket, Guided Tour & Exhibition](https://mediaim.expedia.com/localexpert/44627037/a0dddb0f-0671-4eec-93d3-e6dee1d124bd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### The Royal Mint Experience: Ticket, Guided Tour & Exhibition

$23

per adult

**100%** of travellers recommend

[](https://expedia.com/things-to-do/the-royal-mint-experience-ticket.a44627037.activity-details)

[See all activities in Chepstow](https://expedia.com/things-to-do/search?rid=5618)

## Chepstow Hotel Deals

![Delta Hotels by Marriott St. Pierre Country Club](https://images.trvl-media.com/lodging/1000000/70000/65900/65879/280a23d2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Delta Hotels by Marriott St. Pierre Country Club

St Pierre Park Chepstow Wales

Fully refundableReserve now, pay when you stay

$90 nightly

$108 total

Feb 23 - Feb 24

Total with taxes and fees

8.2/10 Very Good! (1,001 reviews)

Yes all good

Reviewed on Feb 12, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F23%2F2026&endDate=2%2F24%2F2026&selected=65879&PinnedHotelID=65879&HadPinnedHotel=true&regionId=5618)

![Two Rivers, Chepstow by Marston’s Inns](https://images.trvl-media.com/lodging/32000000/31890000/31887100/31887058/bdb658ee_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Two Rivers, Chepstow by Marston’s Inns

Newport Road Chepstow Wales

Fully refundableReserve now, pay when you stay

$61 nightly

$73 total

Mar 1 - Mar 2

Total with taxes and fees

9/10 Wonderful! (408 reviews)

Rooms are clean and spotless

Reviewed on Feb 10, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=31887058&PinnedHotelID=31887058&HadPinnedHotel=true&regionId=5618)

![Clayton Hotel Bristol City](https://images.trvl-media.com/lodging/70000000/69830000/69825700/69825633/95670123_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Clayton Hotel Bristol City

Broad Street Bristol England

Fully refundableReserve now, pay when you stay

$97 nightly

$117 total

Feb 22 - Feb 23

Total with taxes and fees

9/10 Wonderful! (1,208 reviews)

Great location near bus station and Hippodrome. Next to Corn st where there are great pubs and restaurants. Clean and friendly Modern rooms with all you need

Reviewed on Feb 14, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=69825633&PinnedHotelID=69825633&HadPinnedHotel=true&regionId=5618)

[See all 3,221 properties in Chepstow](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F17%2F2026&endDate=2%2F18%2F2026&regionId=5618)

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](https://www.expedia.com/Chepstow-Castle-Cardiff.d6086505.Vacation-Attraction), [Chepstow Castle](https://www.expedia.com/Chepstow-Castle-Cardiff.d553248621563222749.Vacation-Attraction) and [Caldicot Castle](https://www.expedia.com/Caldicot-Castle-Caldicot.d553248621532491483.Vacation-Attraction) |

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## Frequently asked questions

### How much does a Chepstow vacation package cost?

### What are the cheapest months to go to Chepstow?

### How many days is enough for Chepstow?

### Is it worth booking a vacation package to Chepstow?

### How to find the best Chepstow package deals?

### Is it cheaper to book a Chepstow vacation as a package?

### When to book a vacation package to Chepstow?

### 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](https://www.expedia.com/why/trip-planning) 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](https://www.expedia.com/Things-To-Do-In-Chepstow.d5618.Travel-Guide-Activities) with our dedicated travel guide.

### Does Expedia offer Book Now, Pay Later Chepstow vacation packages?

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.