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.
Sandman Signature Dartmouth Hotel & Suites
Price was CA $1,110, price is now CA $816 per person
CA $816
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.4/10 Exceptional! (2,523 reviews)
Did a one night stay before we flew out, hotel was super clean, staff were welcoming. It was close to the airport. Would stay again!
Reviewed on May 31, 2026
Chateau Bedford, Trademark Collection by Wyndham
Birch Cove
Price was CA $1,031, price is now CA $825 per person
CA $825
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.2/10 Wonderful! (2,129 reviews)
Central location for Halifax Bedford, good staff, breakfast included.
Reviewed on May 31, 2026
Liscombe Lodge Resort and Conference Centre
Price was CA $1,019, price is now CA $820 per person
CA $820
per person
Aug 19 - Aug 23
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
8.4/10 Very Good! (307 reviews)
Booking through Expedia said “River view”; however given a room “On the River”. Best to call the lodge to book in order to be clear on the room you want. A little extra cleaning can go a long way in the pool and cabins, but they just opened the week we went so I feel it probably will improve throughout the year. The staff (especially Sharon at the front desk), dinner menu and things to do in the area made it a 5/5.
Reviewed on May 17, 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 14 to Jun 15
CA $205
CA $234 total
Jun 14 - Jun 15
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 $148 per night from Jun 4 to Jun 5
CA $148
CA $169 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 $229 per night from Jun 14 to Jun 15
CA $229
CA $261 total
Jun 14 - Jun 15
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"The staff was very very friendly, the breakfast was good the rooms were clean and quiet. Our grandson really enjoyed the pool. The location of the hotel is excellent with shopping and restaurants across the road. Will definitely be staying there again."
Reviewed on May 31, 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.
