Chepstow Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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.

Top Chepstow Vacation Deals

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

Langford Executive Apartments

3.5 out of 5
Price was CA $1,868, price is now CA $1,675 per person
CA $1,675
per person
Mar 22 - Mar 28
found 9 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Bristol (BRS)
8/10 Very Good! (1 review)
Lucknam Park, Emblems Collection

Lucknam Park, Emblems Collection

5 out of 5
Price was CA $3,705, price is now CA $3,314 per person
CA $3,314
per person
Mar 22 - Mar 28
found 9 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Bristol (BRS)
9.6/10 Exceptional! (189 reviews)
Lovely room. Superb staff

Reviewed on Dec 16, 2025

Best Western Walton Park Hotel

Best Western Walton Park Hotel

3 out of 5
Price was CA $1,835, price is now CA $1,677 per person
CA $1,677
per person
Mar 22 - Mar 28
found 9 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Bristol (BRS)
8/10 Very Good! (771 reviews)
Fabulous breakfast. Rooms are fine although our shower had poor pressure. Lovely location and grand old building. Recommended but make sure you state you want a good shower at check in and check it when you arrive. Really nice staff and a great stay

Reviewed on Jan 26, 2026

Shepherds Hut Near Exmoor National Park

Shepherds Hut Near Exmoor National Park

2.5 out of 5
Price was CA $2,352, price is now CA $2,160 per person
CA $2,160
per person
Mar 16 - Mar 21
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Bristol (BRS)
6.8/10 (5 reviews)
What a lovely stay! The place was quirky and surrounded by nature, peaceful and a great break from London. Our host was friendly and helpful. Would definitely go back.

Reviewed on Jul 28, 2021

Ready to book your vacation to Chepstow?

 

Choose your dates

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
The price is CA $122 per night from Feb 8 to Feb 9
CA $122
CA $146 total
Feb 8 - Feb 9
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
Value for money

Reviewed on Feb 2, 2026

Delta Hotels by Marriott St. Pierre Country Club
Two Rivers, Chepstow by Marston’s Inns

Two Rivers, Chepstow by Marston’s Inns

4 out of 5
Newport Road Chepstow Wales
Fully refundableReserve now, pay when you stay
The price is CA $82 per night from Feb 22 to Feb 23
CA $82
CA $99 total
Feb 22 - Feb 23
includes taxes & fees
9/10 Wonderful! (404 reviews)
I have a great day rooms are clean and tidied and it’s a peaceful place to rest.

Reviewed on Jan 31, 2026

Two Rivers, Chepstow by Marston’s Inns
Delta Hotels by Marriott Bristol City Centre

Delta Hotels by Marriott Bristol City Centre

4 out of 5
2 Lower Castle Street Bristol England
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Mar 1 to Mar 2
CA $99
CA $119 total
Mar 1 - Mar 2
includes taxes & fees
8.6/10 Excellent! (558 reviews)
Excellent hotel

Reviewed on Feb 1, 2026

Delta Hotels by Marriott Bristol City Centre
See all 3,270 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Chepstow

Millennium Stadium which includes modern architecture and a river or creek

Principality Stadium

4/5(4 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
Cardiff Castle featuring château or palace, heritage architecture and heritage elements

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.

Cardiff Castle
Aerial panorama of Barry Island, Wales, UK

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.

Barry Island Beach

What to do in Chepstow

A tour arrives at Caerleon.

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

CA $168
per adult
The Wandering Bard's Valley Tour or the Swansea Bay Tour.
Cardiff Bay Boat Tour

Cardiff Bay Boat Tour

CA $24
per adult
76% of travellers recommend
Cardiff Bay Boat Tour
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

CA $156
per adult
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour
See all activities in Chepstow

Explore a world of travel with Expedia

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