Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

Your Chester Holiday

Book a custom holiday package to Chester and prepare to experience this city how you want. Consider spending time in the neighbourhood of Garden Lots, which is great for watersports and lots more. If your trip to Chester includes a little sightseeing, check out well-known attractions like Oak Island, Chester Golf Club and Graves Island Provincial Park. Whoever you're heading away with and whatever your budget, your ultimate Chester holiday is just a few clicks away with Expedia.

Chester Holiday

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

Our pick of the best Chester Hotel Deals

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 AU$226 per night from 19 July to 20 July
AU$226
19 July - 20 July
includes taxes & fees
8/10 Very good! (983 reviews)
"The room could be cleaner, there was a weird smell."

Reviewed on 9 July 2026

Travelodge by Wyndham Bridgewater
Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
The price is AU$275 per night from 10 Aug to 11 Aug
AU$275
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very good! (515 reviews)
"lots of fun activities to do, Outdoor pool excellent"

Reviewed on 9 July 2026

Oak Island Resort & Conference Centre
Atlantic View Motel and Cottages

Atlantic View Motel and Cottages

3 out of 5
230 Mason's Beach Road, RR#2 Lunenburg NS
Fully refundableReserve now, pay when you stay
The price is AU$284 per night from 19 July to 20 July
AU$284
19 July - 20 July
includes taxes & fees
9/10 Wonderful! (617 reviews)
"Belle déco, bien aménagé et rénové"

Reviewed on 8 July 2026

Atlantic View Motel and Cottages
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
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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

How much does a Chester holiday package cost?
You'll find cheap prices on Expedia for your Chester getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your holiday to Chester costs.
What are the cheapest months to go to Chester?
The off-season is the best time to travel to Chester if you're hoping to keep costs down. Another tip for getting cheap Chester holiday packages? Try to avoid public holidays and any major festivals or events.
How many days is enough for Chester?
Usually, a handful of days is enough for a Chester holiday. With a well-organised schedule, you can see all the best attractions including Chester Golf Club, as well as explore some hidden gems along the way.
Is it worth booking a holiday package to Chester?
Known for its watersports and home to popular attractions like Chester Golf Club, a Chester holiday is sure to leave an impression. Another top sight to check out? Don't miss Tancook Island.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Chester package deal right away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chester escape underway.
Is it cheaper to book a Chester holiday as a package?
You can enjoy significant savings on your Chester getaway by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to see some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Chester?
If you're planning a spur-of-the-moment Chester getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Chester?

  1. Pick your dates: What you plan to do in Chester and your favourite season can help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your hotel will likely be the largest expense during your trip to Chester.
  3. Decide how long to go away for: Now that you're up to speed on Chester, you can work out the right length of your holiday. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  4. Combine your airfare and accommodation: Once you've settled on your trip dates and duration, book the ideal Chester holiday package for you.

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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.