Chepstow Holidays from £2,734

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

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.
The Great George

The Great George

5 out of 5
Downtown Charlottetown
per person
18 Oct - 25 Oct
found 11 hours ago
Return direct flight included
London (LON) to Charlottetown (YYG)
9.8/10 Exceptional! (1,010 reviews)
The property is an amalgamation of several heritage building's cover a block of Great George St. The staff was amazing and the room was spacious and comfortable

Reviewed on 11 Aug 2025

Clinton Pond Bed and Breakfast

Clinton Pond Bed and Breakfast

4 out of 5
per person
18 Oct - 25 Oct
found 11 hours ago
Return direct flight included
London (LON) to Charlottetown (YYG)
9.8/10 Exceptional! (8 reviews)
Fox Harb' r Resort

Fox Harb' r Resort

4 out of 5
per person
18 Oct - 25 Oct
found 11 hours ago
Return direct flight included
London (LON) to Charlottetown (YYG)
9.4/10 Exceptional! (97 reviews)
Check in was 3pm. We got there at 2:30 and got into our townhouse at 3:45pm. They did give us a bottle of white wine (which I don’t drink) and breakfast vouchers. Breakfast was delicious and the vouchers were appreciated. Hot tub, cold tub and sauna were out of commission the 3 days we were there. The pool and steam room were great. The golf course is under renovations so there is a lot of dirt and sand flying through the air when it is windy, which it was. Biking around the property is fun but the wind can make it dusty and dirty too. Staff was super friendly but I agree with others who say that if you don’t appear wealthy you seem to be treated differently.

Reviewed on 10 Aug 2025

By The Bay Cottages

By The Bay Cottages

3 out of 5
per person
18 Oct - 25 Oct
found 11 hours ago
Return direct flight included
London (LON) to Charlottetown (YYG)
8.2/10 Very Good! (19 reviews)
Sunny and staff were very nice. Cottage was clean and comfortable. Pool was great. Nice location and very quiet.

Reviewed on 16 Jul 2025

45 Steps - The Culinary Beachside Inn

45 Steps - The Culinary Beachside Inn

5 out of 5
per person
18 Oct - 25 Oct
found 11 hours ago
Return direct flight included
London (LON) to Charlottetown (YYG)
10/10 Exceptional! (48 reviews)
Excellent Inn - very clean and well maintained. Thomas and Barbara are excellent hosts. The dining experience us great with fresh home made food prepared every day. We really enjoyed our stay.

Reviewed on 29 Jul 2025

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

Singing Sands Inn Motel

Singing Sands Inn Motel

2.5 out of 5
2518 East Point Road – RTE 16, Kingsboro, Kingsboro, PE
The price is £76 per night from 17 Aug to 18 Aug
£76
17 Aug - 18 Aug
includes taxes & fees
7.4/10 Good! (131 reviews)
"The staff were very kind and the property was very close to the beautiful beach at Basin Head provincial park."

Reviewed on 6 Aug 2025

Singing Sands Inn Motel
The Barn at Spry Point

The Barn at Spry Point

2 out of 5
222 Ark Lane Lot B The Barn, Little Pond, PE
The price is £71 per night from 24 Aug to 25 Aug
£71
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (46 reviews)
"Very clean, staff were nice and the property was BEAUTIFUL"

Reviewed on 8 Aug 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 £140 per night from 18 Aug to 19 Aug
£140
18 Aug - 19 Aug
includes taxes & fees
9.6/10 Exceptional! (218 reviews)
"We enjoyed our stay, the view is magnificent! Beautiful sunset and sunrise, we enjoyed watching a couple of seals playing in the ocean."

Reviewed on 1 Aug 2025

Johnson Shore Inn
See all 109 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chepstow travel package cost?
From as little as £2,734. Yes, you read that correctly. Our Chepstow packages are the best way to make your budget stretch further. Combine your favourite hotels, flights and rental car and explore this fabulous destination.
If I'm not able to travel, can I cancel my Chepstow travel package?
Your situation can change in a flash, so yes, you can. You may be able to change or cancel your Chepstow travel package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel or make changes, but your airline, hotel or car rental company may impose a fee. Looking for more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Chepstow?
Bundle your hotels and flights with Expedia to save on your next adventure. With more than 550 air carriers and 1,000,000 properties globally, your Chepstow holiday package can be tailored exactly to suit your budget. With all those extra dollars, why not add some awesome experiences and tours? It's an easy way to unlock even more bargains. The holiday you've always dreamed of in Chepstow is much closer than you thought!
Does Expedia offer Book Now, Pay Later Chepstow holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has devised a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a terrific getaway without drying up your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: Like the idea of paying for your holiday in multiple transactions? Consider this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan from Klarna.

Where should I stay in Chepstow?
With interesting attractions like Souris Lighthouse and Souris Ferry Terminal in this neighbourhood, try to find a hotel near either one. Souris Visitor Information Centre is another Chepstow hot spot that lures the crowds.
What are the top hotels in Chepstow?
If it's your first time staying in Chepstow, secure a room at Kindred Spirits Inn & Cottages or Sherwood Inn and Motel. Both have good amenities and are favourites among many travellers.
How far in advance should I book my Chepstow holiday?
Savvy travellers book early. Airlines generally release flights nearly 12 months in advance, and this is a great opportunity to score some of the cheapest prices. Just been told you should take some holiday time next month? No need to worry. Expedia are never short of fantastic deals to help you have the getaway of your dreams, at an affordable price.
What does an Expedia Chepstow travel package include?
Expedia has everything you need to plan your Chepstow trip, but how you structure your package is your call. Pick from any combination of rental cars, flights and hotels. Looking for some activities to keep you on the move? Once you've made your booking, you can add them on too. No matter your budget, there's a travel package to meet your needs.
What should I know before booking a Chepstow travel package?
You can save a tidy sum by bundling your hotels, airfares and rental cars. Once you've made your booking, you can add on activities or sightseeing tours. Your next awesome holiday is only a couple of clicks away.
Can I choose my airline with a Chepstow Expedia travel package?
With a travel package, you're in control. Whether you'd prefer to fly to Chepstow in coach or first class, simply choose from the available airline options. Expedia has access to more than 550 airline partners worldwide.

* 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.