Chester

Travel Guide

Chester featuring a house and a small town or village
Chester which includes boating, a coastal town and a bay or harbor
Chester showing a bay or harbor, a coastal town and general coastal views
Chester showing a house
Chester showing flowers
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
Fully refundableReserve now, pay when you stay
The price is ¥17,601 per night from Jan 4 to Jan 5
¥17,601
¥20,065 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Cookville. Enjoy free breakfast, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,000 reviews)
Clean rooms

Reviewed on Nov 30, 2025

Best Western Plus Bridgewater Hotel & Convention Centre
Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
49 North St Bridgewater NS
The price is ¥14,830 per night from Dec 14 to Dec 15
¥14,830
¥17,935 total
Dec 14 - Dec 15
includes taxes & fees
Stay at this hotel in Bridgewater. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
8/10 Very Good! (909 reviews)
Room was clean

Reviewed on Dec 2, 2025

Travelodge by Wyndham Bridgewater
Smugglers Cove Inn

Smugglers Cove Inn

4 out of 5
139 Montague Street Lunenburg NS
The price is ¥18,012 per night from Dec 29 to Dec 30
¥18,012
¥20,534 total
Dec 29 - Dec 30
includes taxes & fees
Stay at this hotel in Lunenburg. Enjoy free WiFi, daily housekeeping, and premium bedding. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (763 reviews)
Everything was great! Such a cute place. Was nice for a weekend get away.

Reviewed on Nov 25, 2025

Smugglers Cove Inn
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.
Black Forest Cabins

Black Forest Cabins

3 out of 5
15 Longhill Rd Mahone Bay NS
Book a stay at this spa cabin in Mahone Bay. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mahone Bay Swimming Pool and Have A Yarn ...
9.8/10 Exceptional! (18 reviews)
Very clean, calm place but still walk g distance to town amenities. Sauna was fabulous.,

Reviewed on Nov 30, 2025

Black Forest Cabins
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

Indian Harbour NS
Stay at this cottage in Indian Harbour. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Swissair Flight 111 Memorial and Indian Harbour ...
10/10 Exceptional! (84 reviews)
A great place to stay. Very clean and cozy. Decorated very tastefully. Local Acadian restaurant was perfect. Would love to go back again.

Reviewed on Oct 27, 2025

Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove
One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage

Mahone Bay NS
Stay at this cottage in Mahone Bay. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Jubilee Park and Have A Yarn are located ...
10/10 Exceptional! (104 reviews)
Everything was excellent. A bar of soap for the shower would have been nice.

Reviewed on Oct 30, 2025

One bedroom fully equipped Mahone Bay luxury cottage
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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