Chester Holidays from £601

Book a Hotel + Flight or Car together to unlock savings

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
Lux Exec Home HFX Waterfront Pool Hot Tub
Super 8 by Wyndham Windsor NS
The Barrington Hotel
Chateau Bedford, Trademark Collection by Wyndham

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

Family Home In the Heart of the Village of Chester

Family Home In the Heart of the Village of Chester

Chester, NS
9.4/10 Exceptional! (23 reviews)
Chester Nova Scotia
"This is a great whole home property that offers a lot of easy trip options. There is a super cute small downtown that is a good spot for breakfast / shopping. There is a grocery store super close to the house and the kitchen is well equipped for any meal. The home has no AC but did provide fans. ..."

Reviewed on 6 Jul 2025

Family Home In the Heart of the Village of 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 £122 per night from 4 Aug to 5 Aug
£122
4 Aug - 5 Aug
includes taxes & fees
8/10 Very Good! (744 reviews)
"Outstanding and helpful service staff and front desk help that went out of their way to be helpful."

Reviewed on 30 Jul 2025

Travelodge by Wyndham Bridgewater
Miller House By the Bay

Miller House By the Bay

2 out of 5
624 Main street, mahone bay, NS
The price is £96 per night from 6 Aug to 7 Aug
£96
6 Aug - 7 Aug
includes taxes & fees
9.6/10 Exceptional! (36 reviews)
"We loved EVERYTHING about this place: Margaret, our host, was warm and welcoming. The accommodations were comfortable. Continental breakfast with home-made goodies was a good way to start the day. And Mahone Bay is one of our favourite destinations in Nova Scotia."

Reviewed on 31 Jul 2025

Miller House By the Bay
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.

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.

* 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.