Chester Holidays from £969

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Your Chester Holiday

Take the hassle out of travel planning with a Chester holiday package. A great neighbourhood to base yourself in this captivating city is Garden Lots, which is good for watersports and much more. A trip to Chester is a superb opportunity to sightsee. Be sure to visit well-known attractions like Oak Island, Tancook Island and Chester Golf Club. Stop dreaming and start travelling. Browse the wide range of options on Expedia today and finally put your Chester holiday plans into action!

Top Chester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
South West Mermaid Inn

South West Mermaid Inn

2.5 out of 5
Price was £1,133, price is now £969 per person
£969
per person
16 Aug - 23 Aug
found 1 day ago
Return direct flight included
London (LON) to Halifax (YHZ)
8.2/10 Very good! (770 reviews)
The room was clean and well maintained. The staff was very friendly and helpful. Check in was quick and easy and so was check out.

Reviewed on 13 Jul 2026

Seacliff- Luxury Halifax Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Seacliff- Luxury Halifax Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

4.5 out of 5
Price was £1,980, price is now £1,525 per person
£1,525
per person
5 Oct - 9 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Halifax (YHZ)
10/10 Exceptional! (6 reviews)
Brought the family on a little east coast getaway and couldn't ask for a better location to return to and unwind in the evenings. Spectacular views on a peaceful cove with every accommodation you could ever need. Exceptional, absolutely loved it!

Reviewed on 22 Jun 2026

Riverside Inn

Riverside Inn

3 out of 5
Price was £1,388, price is now £1,174 per person
£1,174
per person
16 Aug - 23 Aug
found 1 day ago
Return direct flight included
London (LON) to Halifax (YHZ)
9.6/10 Exceptional! (211 reviews)
Fantastic little inn with charming touches!

Reviewed on 6 Jul 2026

The Sutton Place Hotel Halifax

The Sutton Place Hotel Halifax

5 out of 5
Downtown Halifax
Price was £1,311, price is now £1,128 per person
£1,128
per person
31 Aug - 4 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Halifax (YHZ)
9.6/10 Exceptional! (2,169 reviews)
.

Reviewed on 12 Jul 2026

Brier Island Lodge

Brier Island Lodge

3 out of 5
Price was £1,333, price is now £1,149 per person
£1,149
per person
16 Aug - 23 Aug
found 1 day ago
Return direct flight included
London (LON) to Halifax (YHZ)
8.4/10 Very good! (471 reviews)
The room was clean, the staff we friendly and helpful. The views were spectacular. Breakfast and dinner were delicious and made with care. Overall it was a great stay and would recommend this place as a stop on your trip.

Reviewed on 12 Jul 2026

Chester Essential Information

Language
English
Currency
Canadian dollars
Population
1,550
Max Temp Winter
2ºC
Max Temp Summer
21ºC
Top Sights
Bayswater Beach Provincial Park, Chester Playhouse and Lordly House Museum

Top hotels in Chester

Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
49 North St Bridgewater NS
Fully refundableReserve now, pay when you stay
The price is £120 per night from 17 Jul to 18 Jul
£120
17 Jul - 18 Jul
includes taxes & fees
8/10 Very good! (988 reviews)
"Joann…mgr…to be commended for out of the way service."

Reviewed on 12 Jul 2026

Travelodge by Wyndham Bridgewater
Atlantic View Motel and Cottages

Atlantic View Motel and Cottages

3 out of 5
230 Mason's Beach Road, RR#2 Lunenburg NS
The price is £154 per night from 17 Jul to 18 Jul
£154
17 Jul - 18 Jul
includes taxes & fees
9/10 Wonderful! (617 reviews)
"Belle déco, bien aménagé et rénové"

Reviewed on 8 Jul 2026

Atlantic View Motel and Cottages
Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

3.5 out of 5
527 Highway 10 Exit 12 Cookville NS
Fully refundableReserve now, pay when you stay
The price is £168 per night from 19 Jul to 20 Jul
£168
19 Jul - 20 Jul
includes taxes & fees
9.2/10 Wonderful! (1,014 reviews)
"stay was comfy and close to nearby resturants boston pizza, breakfast was good"

Reviewed on 12 Jul 2026

Best Western Plus Bridgewater Hotel & Convention Centre
See all 320 properties in Chester
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
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Stay near popular Chester attractions

Tancook Island

Find out about the history of Chester when you take a trip to Tancook Island. While in this family-friendly area, you can savour the top-notch restaurants.
See properties

Frequently asked questions

Why should I book my Chester holiday with Expedia?
Choose Expedia to plan your next big escape simply and all in one convenient place. Our top tip for landing a great deal on a Chester retreat? Bundle your hotel, flights and/or hire car into a package holiday. Then throw in a couple of exciting tours and activities. Most bookings also include flexible cancellation policies, so there's no need to worry if you have to change your travel plans. Round-the-clock assistance with cancelling and changing your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Chester?
Chester is a popular place in March, May and July. If you don't like crowds and prefer a calmer pace, book your getaway for November, December and January. To give you an idea of what type of weather to expect, the average temperature during the day in January, the coolest time of year in Chester, is -2ºC. The warmest period here is August, when temperatures hit an average of 19ºC.
What is the top hotel for my holiday in Chester?
Offering many of the creature comforts of home, Oak Island Resort & Conference Centre will make the ideal base for your Chester trip.
How do I get a cheap holiday to Chester?
Bundle your flight and hotel bookings, throw in extras such as tours, and save with a Chester holiday. You won't just enjoy awesome discounts on your escape — you'll have loads of choice within your reach too. When you book with Expedia, you'll have your pick of over 400 air carriers and 321,000 properties around the globe. Your next grand adventure begins right here, right now! Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Chester holiday?
With must-see tourist attractions such as Oak Island and Chester Golf Club, a holiday in Chester promises lots of exciting things to do and see. Swiss Air Flight 111 Memorial Bayswater and Graves Island Provincial Park are a couple of other sights also worth exploring.
What is the best area to stay in when on holiday in Chester?
There's so much to see in Chester, so stay close to its top attractions and spend more time sightseeing. Chester Golf Club is one place that should be on your itinerary.
Do I need a visa for my Chester holiday?
Visa requirements for Chester vary depending on your nationality and reason for your visit. Remember to check official government websites to determine if you need a visa for your holiday. They'll also give you the most up-to-date information, including details about application procedures and any supporting documentation that might be necessary. Research your visa requirements well ahead of time to ensure a hassle-free travel experience. Also check to see that your passport is valid for at least six months from your date of return.
What should I wear on my Chester holiday?
Though everyone's style varies, it can be helpful to have a few guidelines for what to bring during your holiday in Chester. Think about browsing social media before you leave for inspiration on local fashion trends. Pack with confidence by checking the weather forecast in Chester. August brings the warmest temperatures, with daytime averages of 19ºC, while January days average -2ºC, making it the coolest time of year.
What does an Expedia Chester holiday include?
Flights, hotels and a reliable car for all your road trip adventures. Simply pick and choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on some experiences and tours and watch your savings stack up. When it comes to creating your Chester getaway, you're the one in control! Private holiday homes and cottages are a few popular property types in Chester. No matter your holiday style or size of your group, you can count on Expedia for the freedom to personalise your next escape.
Does Expedia offer Book Now, Pay Later Chester holidays?
Yes. Expedia has partnered with online lender Klarna to help you easily pay for your trip in manageable instalments. Simply click on the payment plan that works for you during checkout and take the stress out of budgeting for your trip. Make sure you bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna offers just that! Paying in several transactions will make your holiday dreams possible.
  • No-deposit holidays: When you want to jump on an amazing deal but your budget doesn't quite cover it yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your getaway.

Can I choose my airline with a Chester Expedia holiday?
Yes, you can. We have more than 400 airline partners across the globe, so select the carrier that's a good fit for your travel preferences.

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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.