Chester Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Chester

Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

49 North St Bridgewater NS
Fully refundableReserve now, pay when you stay
S$218
6 Sept - 7 Sept
includes taxes & fees
Travelodge by Wyndham Bridgewater
Bridgewater Hotel

Bridgewater Hotel

35 High St. Bridgewater NS
Fully refundableReserve now, pay when you stay
S$149
16 Sept - 17 Sept
includes taxes & fees
6/10 (482 reviews)
"Non entretenu et malpropre"

Reviewed on 23 Aug, 2026

Bridgewater Hotel
Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

527 Highway 10 Exit 12 Cookville NS
Fully refundableReserve now, pay when you stay
S$259
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"Bartender, Evan and all staff were very nice!"

Reviewed on 21 Aug, 2026

Best Western Plus Bridgewater Hotel & Convention Centre
See all 326 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.

Stay near popular Chester attractions

Chester

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

Chester Golf Club

8.4/10 (28 reviews)
Enjoy a round of golf in Chester at Chester Golf Club. Stroll along this family-friendly area's waterfront or simply enjoy its seafood restaurants.
See properties

Chester Playhouse

8.6/10 (12 reviews)
You can enjoy a show at Chester Playhouse on your trip to Chester. Stroll along this family-friendly area's waterfront or simply enjoy its seafood restaurants.
See properties

Chester Art Center

8.8/10 (3 reviews)
You can spend an afternoon studying the exhibits at Chester Art Center during your trip to Chester. Stroll along this family-friendly area's waterfront or simply enjoy its seafood restaurants.
See properties

Lordly House Museum

8.8/10 (3 reviews)
You can spend time browsing the exhibits at Lordly House Museum during your travels in Chester. While in this family-friendly area, you can savour the top-notch restaurants.
See properties

St. Stephen's Church

9.2/10 (11 reviews)
After visiting St. Stephen's Church, make a plan to see the other sights and activities in Chester. Amble around this family-friendly area's waterfront or experience its entertainment venues.
See properties

Valverde Studio Gallery

You can spend time studying the exhibits at Valverde Studio Gallery during your travels in Chester. Stroll along this family-friendly area's waterfront or simply enjoy its seafood 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.