Chepstow Holidays from £923

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Your Chepstow Holiday

The stress-free way to experience this lively city is with a custom-made Chepstow holiday package. Stay in the neighbourhood of East Point, which is great for history, nature and watersports or choose someplace else — our packages are all about you. If seeing the sights is a priority during your trip to Chepstow, make sure you check out leading attractions like Basin Head Provincial Park and Basin Head Fisheries Museum. No matter your travel plans or budget, organising your ultimate tailored Chepstow holiday is simple with Expedia.

Top Chepstow Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Traveller's Inn
Prince County Guest House
Sunflower Guest Suites

Chepstow Essential Information

Language
English
Currency
Canadian dollars
Top Sights
Basin Head Provincial Park, Sallys Beach Provincial Park and Red Point Provincial Park

Top hotels in Chepstow

Wheelhouse Inn: Unit #3

Wheelhouse Inn: Unit #3

Georgetown PE
The price is £137 per night from 24 May to 25 May
£137
24 May - 25 May
includes taxes & fees
Wheelhouse Inn: Unit #3
The Barn at Spry Point

The Barn at Spry Point

2 out of 5
222 Ark Lane Lot B The Barn Little Pond PE
Fully refundableReserve now, pay when you stay
The price is £75 per night from 20 May to 21 May
£75
20 May - 21 May
includes taxes & fees
9/10 Wonderful! (66 reviews)
Lovely stay -- beautiful setting, helpful proprietor, comfortable accomodations.

Reviewed on 23 Nov 2025

The Barn at Spry Point
Johnson Shore Inn

Johnson Shore Inn

3 out of 5
9984 Northside Road, Route 16 Rock Barra PE
The price is £122 per night from 20 May to 21 May
£122
20 May - 21 May
includes taxes & fees
9.8/10 Exceptional! (240 reviews)
This place was among the best boutique bed and breakfast hotels I have been to. The property was beautiful. The corner room has amazing views of the sea and the wide open yard by the cliff - the location was beautiful. Dave & Mellanie were great hosts. Dave made us the breakfast himself while we ...

Reviewed on 14 May 2026

Johnson Shore Inn
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.