Chester

Travel Guide
Chester which includes boating, a bay or harbour and a coastal town
Stay in a beautiful coastal location that delights with its beaches, islands and waterways. Hike, bike and sail through the picturesque area.

Founded in 1759 during the French and Indian War, Chester is one of the oldest communities on the east coast of Nova Scotia. Escape to the scenic shores of this coastal village to relax on its beaches, to sail across its waterways and to explore the neighboring islands.

With cold winters and wet springs, Chester is more of a summer destination. Find a pretty beach in front of the village, just off Peninsular Road. Dip your feet in the cool water and watch as yachts and trawlers make their way to and from the harbor. 

A great way to spend the day is to tour the beautiful islands and waterways of St. Margret’s Bay. Hop aboard the ferry and stop off at Tancook Island. The 50-minute voyage travels to the two parts of the island: Little Tancook and Big Tancook. During your trip you will pass by many of Mahone Bay’s islands and may see porpoises and seals. 

Tancook Island has some interesting beaches, including the “fossil beach” near where the ferry docks on Big Island. Hunt for a precious souvenir of millennia-old life frozen in time. Look for crabs, starfish and other marine creatures in rock pools. Hike or bike across the island landscapes and go bird watching on Big Tancook, where more than 70 species of resident and migratory birds can be seen.

Return to Chester and enjoy an evening performance at the Chester Playhouse. The cultural venue presents live theater and music throughout the year. Bring your day to an end at one of the many restaurants that overlook the bay.

Consider planning your trip to coincide with Chester Race Week. The annual sailing regatta takes place around the middle of August and features teams from across North America. In addition to the spectacle on the water, there is live music and a big party at the end of the week.

You can reach Chester by flying into the international airport at Halifax. From here, it’s about a 1-hour drive south to the scenic coastal spot.

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
The price is CA $167 per night from May 20 to May 21
CA $167
CA $192 total
includes taxes & fees
May 20 - May 21
Stay at this 3.5-star business-friendly hotel in Cookville. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the pool ...
9.2/10 Wonderful! (738 reviews)
"Under construction, so breakfast was lacking."

Reviewed on May 9, 2024

Best Western Plus Bridgewater Hotel & Convention Centre
Smugglers Cove Inn
Smugglers Cove Inn
4 out of 5
139 Montague Street, Lunenburg, NS
The price is CA $188 per night from May 14 to May 15
CA $188
CA $216 total
includes taxes & fees
May 14 - May 15
Stay at this hotel in Lunenburg. Enjoy free WiFi, daily housekeeping, and a hair salon. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (486 reviews)
Very well situated.
"Very well positioned for the waterfront and restaurants. Kind and helpful management and staff."

Reviewed on May 1, 2024

Smugglers Cove Inn
Days Inn & Conference Center by Wyndham Bridgewater
Days Inn & Conference Center by Wyndham Bridgewater
2.5 out of 5
50 North Street, Hwy 103 and North Street, Bridgewater, NS
The price is CA $150 per night from May 17 to May 18
CA $150
CA $173 total
includes taxes & fees
May 17 - May 18
Book a stay at this business-friendly hotel in Bridgewater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (963 reviews)
"It was a great stay."

Reviewed on May 5, 2024

Days Inn & Conference Center by Wyndham Bridgewater
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.
Serenity Tiny House Cottage in Chester
Serenity Tiny House Cottage in Chester
Chester
Stay at this cottage in Robinsons Corner. Enjoy free WiFi, a garden, and tennis courts. Our guests praise the property condition in our reviews. Popular attractions ...
10/10 Exceptional! (49 reviews)
Serenity Cottage is a little corner of Heaven
"Sandra and Bill are fantastic hosts, who have built and outfitted this tiny home with such thoughtfulness and intention, that it was very difficult to bid it goodbye. The Southern Shore of Nova Scotia is one of the most beautiful- and friendliest - places I have ever been. Im counting down the days ..."

Reviewed on Oct. 20, 2023

Serenity Tiny House Cottage in Chester
Idyllic, sparkling clean ocean/beach cottage for your spontaneous getaway.
Idyllic, sparkling clean ocean/beach cottage for your spontaneous getaway.
Black Point
Book a stay at this beach cottage in Black Point. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Cleveland Beach Provincial Park and Queensland ...
9.8/10 Exceptional! (105 reviews)
Wonderful seaside escape
"Lovely property ,lovely hosts.spectacular views ,all amenities provided close to everything 👍"

Reviewed on Oct. 16, 2023

Idyllic, sparkling clean ocean/beach cottage for your spontaneous getaway.
On the Beautiful South Shore Near Chester and Hubbards, Ns
On the Beautiful South Shore Near Chester and Hubbards, Ns
Deep Cove
Book a stay at this family-friendly cottage in Deep Cove. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Blandford Nature Reserve ...
9.8/10 Exceptional! (61 reviews)
Fabulous!
"If you are considering staying on the South Shore this property is highly recommended. Everything from start to finish was perfect. It is in a beautiful cove with lovely views from the terrace. Perfect for morning coffee or late evening drinks. The house was clean , spacious and well maintained. ..."

Reviewed on Sep. 2, 2023

On the Beautiful South Shore Near Chester and Hubbards, Ns
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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