Chester Islands Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Plan, book, and manage your trip all in one place

Top hotels in Chester Islands

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 S$234 per night from 10 Jul to 11 Jul
S$234
10 Jul - 11 Jul
includes taxes & fees
8/10 Very Good! (713 reviews)
"The hotel is quite old and breakfast was very simple. In my opion it’s overpriced."

Reviewed on 6 Jul, 2025

Travelodge by Wyndham Bridgewater
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 S$253 per night from 16 Jul to 17 Jul
S$253
16 Jul - 17 Jul
includes taxes & fees
9.2/10 Wonderful! (892 reviews)
"We had a good time, restaurant is very nice - lots of veg options."

Reviewed on 1 Jul, 2025

Best Western Plus Bridgewater Hotel & Convention Centre
Smugglers Cove Inn
Smugglers Cove Inn
4 out of 5
139 Montague Street, Lunenburg, NS
8.8/10 Excellent! (635 reviews)
"Loved our stay"

Reviewed on 5 Jul, 2025

Get rates
Smugglers Cove Inn
See all 311 properties in Chester Islands
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 Islands holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Chester Islands costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester Islands?
You can usually find reduced prices and greater availability in January, February and November. Browse our cheap Chester Islands holiday packages and you could score some great off-season discounts.
How many days is enough for Chester Islands?
The ideal length for your Chester Islands holiday depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to visit all the top sights and discover some hidden treasures along the way.
How to find the best Chester Islands package deals?
Begin your search for a Chester Islands package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Chester Islands package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester Islands getaway off to a flying start.
Is it cheaper to book a Chester Islands holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking stays and flights individually. Better still, you can personalise your Chester Islands getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Chester Islands?
If you've got your Chester Islands holiday dates confirmed, book as soon as you can to snap up some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Chester Islands?

  1. Pick your travel dates: What you want to do in Chester Islands and your favourite season can help you decide when to go.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your hotel will likely be the biggest expense during your trip to Chester Islands.
  3. Determine how many days away: Start by making a list of all the attractions and activities you'd like to get to in Chester Islands. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Chester Islands holiday package that brings all your bookings together.

* 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.