Chester Islands Vacation Packages
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Your Chester Islands Vacation
Prepare to experience Chester Islands on your own terms with a custom Chester Islands vacation package! Discovering the charms of this interesting city is made simpler with a base in a neighborhood such as Garden Lots, which is great for watersports, among other things. Make your trip to Chester Islands even more fulfilling by going sightseeing. Oak Island, Tancook Island and Chester Golf Club are among the leading attractions worth exploring. Whatever your travel plans or budget, putting together the ultimate tailored Chester Islands vacation is a breeze with Expedia.
Top Chester Islands Vacation Deals
Price found within the past 48 hours. Click for updated prices.
South West Mermaid Inn
Price was CA $685, price is now CA $548 per person
CA $548
per person
Aug 14 - Aug 17
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
8.2/10 Very Good! (763 reviews)
Staff was fantastic and breakfast was really good, will stay again when back in area.
Reviewed on May 18, 2026
Sandman Signature Dartmouth Hotel & Suites
Price was CA $1,146, price is now CA $855 per person
CA $855
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.4/10 Exceptional! (2,523 reviews)
We intentionally booked this hotel for the pool and couldn’t use it because it was so busy. We tried multiple times each day and it was packed.
Reviewed on May 30, 2026
Chateau Bedford, Trademark Collection by Wyndham
Birch Cove
Price was CA $1,056, price is now CA $859 per person
CA $859
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.2/10 Wonderful! (2,129 reviews)
great location & service
Reviewed on May 29, 2026
Chester Islands Hotel Deals
Oak Island Resort & Conference Centre
36 Treasure Drive Western Shore NS
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Jun 1 to Jun 2
CA $205
CA $234 total
Jun 1 - Jun 2
includes taxes & fees
8.2/10 Very Good! (495 reviews)
"Clean rooms . Ground level rooms are noisy due to outside traffic and activities from conferences. Surprised that room didn’t have water bottles. Restaurant was very good but limited menu or items on menu were not available."
Reviewed on May 28, 2026
The Homeport Motel
167 Victoria Road Lunenburg NS
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Jun 4 to Jun 5
CA $157
CA $179 total
Jun 4 - Jun 5
includes taxes & fees
9/10 Wonderful! (603 reviews)
"The Homeport Motel is nothing fancy. A good clean motel. Located about 15 minutes from the main pier and shops and restaurants. Quiet with comfy beds. Tim Hortons and NSLC within walking distance. We would stay again."
Reviewed on May 30, 2026
Best Western Plus Bridgewater Hotel & Convention Centre
527 Highway 10 Exit 12 Cookville NS
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Jun 4 to Jun 5
CA $230
CA $262 total
Jun 4 - Jun 5
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Great place to stay, close to everything, you need"
Reviewed on May 30, 2026
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.
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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.
