Chepstow Holidays from £960

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    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.
Prince County Guest House

Prince County Guest House

3.5 out of 5
Price was £1,077, price is now £960 per person
£960
per person
15 Sept - 20 Sept
found 9 hours ago
Return flight included
London (LGW) to Charlottetown Alexander B. Campbell Airport (YYG)
9/10 Wonderful! (208 reviews)

Cavendish Bosom Buddies Cottage Resort

Cavendish Bosom Buddies Cottage Resort

3 out of 5
Price was £1,133, price is now £963 per person
£963
per person
15 Sept - 20 Sept
found 9 hours ago
Return flight included
London (LGW) to Charlottetown Alexander B. Campbell Airport (YYG)
9.6/10 Exceptional! (160 reviews)
We had a great stay...the room was very clean and the hot tub was very relaxing.

Reviewed on 28 Jun 2026

Microtel Inn & Suites by Wyndham Summerside

Microtel Inn & Suites by Wyndham Summerside

3 out of 5
Price was £1,113, price is now £977 per person
£977
per person
15 Sept - 20 Sept
found 9 hours ago
Return flight included
London (LGW) to Charlottetown Alexander B. Campbell Airport (YYG)
9.2/10 Wonderful! (619 reviews)
Very clean but waterslide was only operational for less than 30 minutes.

Reviewed on 1 Jul 2026

Pine Cottages

Pine Cottages

2 out of 5
Price was £1,082, price is now £963 per person
£963
per person
15 Sept - 20 Sept
found 9 hours ago
Return flight included
London (LGW) to Charlottetown Alexander B. Campbell Airport (YYG)
8/10 Very good! (18 reviews)
Lovely clean cottage with everything you need right across from the beach. Would definitely stay here again.

Reviewed on 19 Sept 2025

Charlottetown Inn & Conference Centre

Charlottetown Inn & Conference Centre

3.5 out of 5
Downtown Charlottetown
Price was £1,304, price is now £1,161 per person
£1,161
per person
15 Sept - 20 Sept
found 9 hours ago
Return flight included
London (LGW) to Charlottetown Alexander B. Campbell Airport (YYG)
6/10 (1,448 reviews)
No pool . Renovation going on , says pet friendly but only one building and it’s the old one and it costs 25$ a day too

Reviewed on 1 Jul 2026

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

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 £73 per night from 7 Jul to 8 Jul
£73
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (74 reviews)
"The place is near the water so the views are awesome! The staff was accommodating and welcoming, and the room was clean. Also, the kitchen is very well equipped."

Reviewed on 28 Jun 2026

The Barn at Spry Point
Rollo Bay Inn

Rollo Bay Inn

2.5 out of 5
1067 Lower Rollo Bay Rd Rollo Bay PE
Fully refundableReserve now, pay when you stay
The price is £96 per night from 5 Jul to 6 Jul
£96
5 Jul - 6 Jul
includes taxes & fees
8.2/10 Very good! (16 reviews)
"Jay, the owner, really make you feel welcome and appreciated! The place is really cozy and charming! We really enjoyed our stay! Thanks for the amazing service! I recommend this place!"

Reviewed on 22 Jun 2026

Rollo Bay Inn
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 23 Jul to 24 Jul
£140
23 Jul - 24 Jul
includes taxes & fees
9.8/10 Exceptional! (245 reviews)
"Beautiful views, amazing location right on the ocean, friendly staff and great food!"

Reviewed on 28 Jun 2026

Johnson Shore Inn
See all 119 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 £960. 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.

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. Flight-inclusive packages are ATOL protected.