Chester Islands Holidays from AU$872

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Your Chester Islands Holiday

When you organise a holiday package to Chester Islands, you can relax and enjoy your break knowing that all your travel plans have been made in advance. Discover the many wonders of this lively city while staying in a neighbourhood like Garden Lots, which is great for watersports. Fill your schedule with tours of Oak Island, Chester Golf Club and Graves Island Provincial Park, some of the attractions you should see during your trip to Chester Islands. A couple of clicks is all it takes to craft a tailored Chester Islands holiday on Expedia.

The Latest Chester Islands Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Coastal Inn Halifax

Coastal Inn Halifax

3 out of 5
Price was AU$1,103, price is now AU$872 per person
AU$872
per person
21 Aug - 24 Aug
found 1 day ago
Return flight included
Calgary (YYC) to Halifax (YHZ)
8.6/10 Excellent! (1,007 reviews)
Spacious room and very clean. Helpful staff, plenty of parking. Great place to stay for Halifax. Taxi or uber $20 - 25 into city

Reviewed on 14 July 2026

The Sutton Place Hotel Halifax

The Sutton Place Hotel Halifax

5 out of 5
Downtown Halifax
Price was AU$1,359, price is now AU$1,092 per person
AU$1,092
per person
21 Aug - 24 Aug
found 1 day ago
Return flight included
Calgary (YYC) to Halifax (YHZ)
9.6/10 Exceptional! (2,169 reviews)
Superb service, location, and food!

Reviewed on 15 July 2026

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was AU$1,114, price is now AU$917 per person
AU$917
per person
21 Aug - 24 Aug
found 1 day ago
Return flight included
Calgary (YYC) to Halifax (YHZ)
9.2/10 Wonderful! (2,170 reviews)
Lovely property, very comfortable!

Reviewed on 15 July 2026

Sandman Signature Dartmouth Hotel & Suites

Sandman Signature Dartmouth Hotel & Suites

3 out of 5
Price was AU$1,103, price is now AU$911 per person
AU$911
per person
21 Aug - 24 Aug
found 1 day ago
Return flight included
Calgary (YYC) to Halifax (YHZ)
9.4/10 Exceptional! (2,594 reviews)
It was lovely

Reviewed on 15 July 2026

Atlantica Hotel Halifax

Atlantica Hotel Halifax

4 out of 5
South End
Price was AU$1,181, price is now AU$990 per person
AU$990
per person
21 Aug - 24 Aug
found 1 day ago
Return flight included
Calgary (YYC) to Halifax (YHZ)
8.6/10 Excellent! (1,309 reviews)
Was great place

Reviewed on 15 July 2026

Chester Islands Holiday

Chester Islands Essential Information

Language
English
Currency
Canadian dollars
Top Sights
Bayswater Beach Provincial Park, Chester Playhouse and Lordly House Museum

Our pick of the best Chester Islands 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$227 per night from 19 July to 20 July
AU$227
19 July - 20 July
includes taxes & fees
8/10 Very good! (991 reviews)
"Close to all amenities and the places we wanted to visit"

Reviewed on 15 July 2026

Travelodge by Wyndham Bridgewater
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$285 per night from 3 Aug to 4 Aug
AU$285
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (622 reviews)
"This was the cleanest place we have ever stayed in, everything was well laid out and anything you could want in an accommodation was available. Definitely would stay there again."

Reviewed on 14 July 2026

Atlantic View Motel and Cottages
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 AU$326 per night from 19 July to 20 July
AU$326
19 July - 20 July
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"stay was comfy and close to nearby resturants boston pizza, breakfast was good"

Reviewed on 12 July 2026

Best Western Plus Bridgewater Hotel & Convention Centre
See all 367 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Chester Islands holiday package cost?
Offering great value package deals from AU$872 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.

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.