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  • Free Wifi
  • Breakfast
  • Sleeps up to: 2
  • Double bed
  • Shower only
  • En suite
  • Private bathroom
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We have 2 Economy double en-suites which are smaller than the normal double en-suites but have the same facilities. They have a comfortable double bed, flat screen TV and tea and coffee making facilities, the en-shuite bathrooms are modern with shower facilities. The 2 economy Doubles are situated on the ground floor.



  • Colour television
  • Free WiFi Internet
  • Tea and coffee making facilities


The First Hurdle Guest House

(17 Guest Reviews)

Guest Ratings

  • 8
  • 4
  • 3
  • 1
  • 1

Review Summary

  • Rooms 3.7
  • Value 3.6
  • Friendliness 4.2
  • Cleanliness 4.4
  • Facilities 3.9
  • Service 4.4
  • Location 4.6

Review Overall Rating

  • 5.0
  • 4.0
  • 3.0
  • 2.0
  • 1.0
  • 4.0

The First Hurdle Guest House Information

Accommodation type

Bed and Breakfast


  • Baggage store
  • Bar
  • Free Internet access (wireless) in public areas
  • Lounge
  • Non-smoking (throughout)
  • Restaurant
  • Bike lock-up
  • Off-site parking

Children's Facilities

  • Cots

Business Facilities

  • Wifi internet


  • Check in: 4:00 PM till 8:00 PM
  • Check out: 10:00 AM
  • Late check-out available
  • Child Policy: No preference
  • Smoking Policy: No smoking
  • Pets: No pets


The First Hurdle is a family-run guest house located in the heart of Chepstow at the foot of the main shopping and restaurant street and a short walk from the town’s famous Norman Castle and picturesque River Wye. The First Hurdle Guest House is completely refurbished and updated to the standards of a modern boutique hotel. It has 12 on-suite letting rooms, a breakfast room, a warm and cosy snug/lounge and a lovely communal garden patio. The property is comprised of two former 18th century town houses in Upper Church Street, Chepstow, but has been run as a guest house for more than 30 years. Local resident Jane Cooper has been the house’s custodian for 14 of those years and is now joined by her son Scott, and daughter Charlotte in making the enterprise a truly family affair. Each guest room has it's own coffee and tea making facilities, a 32 inch flat screen tv, Wi-Fi and complementary shampoos, conditioners and moisturisers. If you should need any guidance about things on the local area don't hesitate to ask. Chepstow and it's surrounding areas are a treasure trove of historical buildings and sites, including it's Norman castle, nearby Caldicot Castle, World famous Tintern Abbey and the Roman fortress at Caerleon. Chepstow sits on the edge of the Wye Valley and the Forest of Dean, both are areas of outstanding natural beauty with plenty to do and see. Let's not forget that Chepstow has one of the country's most well known race courses, but this is not however, why the guest house is called The First Hurdle. It is in fact because Chepstow acts as the starting point of the Offa's Dyke Path, an ancient earthworks thought to be created by King Offa of Murcia in the 8th century. The path roughly follows the border between England and Wales from Chepstow up to the Liverpool Bay in the North, so we are often the first place people stay when attempting this trek. We look forward to welcoming you to The First Hurdle and making your stay as pleasant as possible.


Off-site parking,

Booking Terms and Conditions


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