Chester Holidays

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Chester Holiday

Our pick of the best Chester Hotel Deals

Family Home In the Heart of the Village of Chester
Family Home In the Heart of the Village of Chester
Chester
Great stay multiple families
"Spacious, clean, comfortable, and lots of room for people to spread out. We would happily return."

Reviewed on 27 Apr. 2025

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Family Home In the Heart of the Village of Chester
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 NZ$330 per night from 29 June to 30 June
NZ$330
29 June - 30 June
includes taxes & fees
9.2/10 Wonderful! (878 reviews)
"It was a great place to stay the staff w Ere super friendly and the restaurant there had amazing food with good prices, large ground for my little fur baby as well and really nice place to stay"

Reviewed on 18 Jun. 2025

Best Western Plus Bridgewater Hotel & Convention Centre
Smugglers Cove Inn
Smugglers Cove Inn
4 out of 5
139 Montague Street, Lunenburg, NS
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (621 reviews)
"wonderful location and extremely helpful owners and staff."

Reviewed on 17 Jun. 2025

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Smugglers Cove Inn
See all 266 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.

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.