Title: Chepstow Vacation Packages & Trips 2026 from CA $1,159 | Expedia.ca

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

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

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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](https://www.expedia.ca/Chepstow-Racecourse-Cardiff.d6171652.Vacation-Attraction), [Tintern Abbey](https://www.expedia.ca/Tintern-Abbey-Cardiff.d6086409.Vacation-Attraction) and [Chepstow Castle](https://www.expedia.ca/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.

## Top Chepstow Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![The Beaufort Hotel](https://images.trvl-media.com/lodging/1000000/890000/888400/888319/602343fe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Beaufort Hotel

CA $1,159

per person

Jun 9 - Jun 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Bristol (BRS)

7.6/10 Good! (269 reviews)

Parking is first come first served. We had no issue. We did go around twice as we missed the entrance. Room was clean and comfortable. We would have liked a firmer mattress. Loved the wonky bits of the building. Breakfast was lovely. Good choice of everything and we asked if we wanted more. Great atmosphere in the bar, seems popular with locals. All staff were very friendly and chatty.

Reviewed on Mar 6, 2026

![Bristol Grand Hotel By Sunday](https://images.trvl-media.com/lodging/1000000/450000/441100/441054/aef50866_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bristol Grand Hotel By Sunday

Bristol City Centre

CA $1,404

per person

May 14 - May 19

found 18 hours ago

Roundtrip flight included

Toronto (YYZ) to Bristol (BRS)

7.8/10 Good! (1,008 reviews)

Bed was very uncomfortable, springs could be felt

Reviewed on Mar 23, 2026

![The Priory Hotel and Restaurant](https://images.trvl-media.com/lodging/18000000/17830000/17828400/17828361/783ccfdd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Priory Hotel and Restaurant

Caerleon

CA $1,407

per person

Jun 9 - Jun 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Bristol (BRS)

9.2/10 Wonderful! (668 reviews)

Staff were wonderful!

Reviewed on Feb 28, 2026

![Holiday Inn NEWPORT by IHG](https://images.trvl-media.com/lodging/1000000/20000/10300/10273/552fe788_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn NEWPORT by IHG

Ringland

CA $1,371

per person

Jun 9 - Jun 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Bristol (BRS)

8/10 Very Good! (478 reviews)

Booked a premium room for myself, partner and toddler. As always room was clean and up to standard. Unfortunately the wifi was not working, so the receptionist quickly switched rooms for us. Unfortunately again wifi was not working and the AC was stuck on cold setting. Mentioned again at the front desk, to which receptionist explained they are getting new wifi and was very apologetic. Third time lucky, we was placed in a standard room, where the wifi and AC was working fine. Staff did note down and mention because we ended up staying in a standard and not premium like booked, they would give a discount for a future booking and meal vouchers. Overall service and staff was very good- we have stayed at this same hotel 4 times previously, so although this time wasn’t our usual excellent stay, it won’t put us off returning.

Reviewed on Dec 26, 2025

![The Miles Arms Hotel](https://images.trvl-media.com/lodging/124000000/123850000/123849400/123849304/8c1bca59_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Miles Arms Hotel

Avonmouth

CA $1,451

per person

May 15 - May 18

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Bristol (BRS)

No reviews

## Ready to book your vacation to Chepstow?

Choose your dates

## Chepstow Hotel Deals

![Delta Hotels by Marriott St. Pierre Country Club](https://images.trvl-media.com/lodging/1000000/70000/65900/65879/01e1c717_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

CA $134

CA $160 total

Mar 29 - Mar 30

includes taxes & fees

8.2/10 Very Good! (1,004 reviews)

Lovely to be pet friendly and have the ability to use the pool and the grounds. Great place to stay and would come again

Reviewed on Mar 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=65879&PinnedHotelID=65879&HadPinnedHotel=true&regionId=5618)

![Two Rivers, Chepstow by Marston’s Inns](https://images.trvl-media.com/lodging/32000000/31890000/31887100/31887058/4682ce7b_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

CA $116

CA $140 total

Apr 20 - Apr 21

includes taxes & fees

9.2/10 Wonderful! (420 reviews)

Yes it was a good place to stay

Reviewed on Mar 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=31887058&PinnedHotelID=31887058&HadPinnedHotel=true&regionId=5618)

![Delta Hotels by Marriott Bristol City Centre](https://images.trvl-media.com/lodging/1000000/10000/5000/4939/1b7bbd4f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Delta Hotels by Marriott Bristol City Centre

2 Lower Castle Street Bristol England

Fully refundableReserve now, pay when you stay

CA $102

CA $123 total

Apr 12 - Apr 13

includes taxes & fees

8.8/10 Excellent! (611 reviews)

The hotel is well placed for the station and shopping, breakfast was very nice. Staff were knowledgeable and friendly and the room i had was perfect for the weekend. I would certainly stay again. The room was also reasonably priced compared to others ive stayed in. A good choice 👌

Reviewed on Mar 21, 2026

[](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=4939&PinnedHotelID=4939&HadPinnedHotel=true&regionId=5618)

[See all 3,351 properties in Chepstow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

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

![Millennium Stadium which includes 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

4/5(5 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.

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

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

#### Cardiff Castle

4.5/5(29 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.

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

![Aerial panorama of Barry Island, Wales, UK](https://images.trvl-media.com/place/6086531/a86c09df-3b2a-4b70-a87e-f2b8f03961ab.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Barry Island Beach

4/5(1 review)

If you’re looking for a quintessential Welsh seaside experience, look no further than Barry Beach in the picturesque Vale of Glamorgan.

[](https://expedia.ca/Barry-Island-Beach-Cardiff.d6086531.Vacation-Attraction)

### What to do in Chepstow

![Cardiff: Gower Peninsula's Cliffs Scenic Day Tour](https://mediaim.expedia.com/localexpert/49556120/542d07dc-66f3-4374-90a2-ba3455fcd4cd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

CA $163

per adult

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

![A tour arrives at Caerleon.](https://mediaim.expedia.com/localexpert/1015104/ec21001a-734f-4e90-a6c3-b7ad50b39792.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### The Wandering Bard's Valley Tour or the Swansea Bay Tour.

CA $166

per adult

[](https://expedia.ca/things-to-do/the-wandering-bards-valley-tour-or-the-swansea-bay-tour.a1015104.activity-details)

![Cardiff Bay Boat Tour](https://mediaim.expedia.com/localexpert/734480/c26ff1e8-74f6-4a14-a3db-1e448a37f7cd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Cardiff Bay Boat Tour

CA $24

per adult

**76%** of travellers recommend

[](https://expedia.ca/things-to-do/cardiff-bay-boat-tour.a734480.activity-details)

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

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