Chester

Travel Guide

A large, two-story house with a steeply pitched roof and a chimney.
A calm lake with several sailboats and a few motorboats.
A coastal scene with multiple boats anchored in the water, a dock, and a building with a green roof.
A large, two-story house with a white porch and multiple windows.
A storefront with a green sign reading "Kiwi Cafe" and a sign below stating "Reserved Kiwi Too".

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 harbour.

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 theatre 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.

Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
49 North St Bridgewater NS
The price is CA $184 per night from Jul 6 to Jul 7
CA $184
per night
Jul 6 - Jul 7
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! (970 reviews)
"Great stay great staff!"

Reviewed on Jun 29, 2026

Travelodge by Wyndham Bridgewater
Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
The price is CA $316 per night from Jul 13 to Jul 14
CA $316
per night
Jul 13 - Jul 14
Book a stay at this business-friendly hotel in Western Shore. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Oak Island and Tancook ...
8.2/10 Very good! (509 reviews)
"I loved the fact that you could stand out on balcony and overlook the entire area. You can walk all around by the ocean where chairs were placed by the water so you could just sit in them, enjoy the hot sun and listen to the ocean while relaxing, watching the clouds sail by, listening to the birds ..."

Reviewed on Jun 28, 2026

Oak Island Resort & Conference Centre
Atlantic View Motel and Cottages

Atlantic View Motel and Cottages

3 out of 5
230 Mason's Beach Road, RR#2 Lunenburg NS
The price is CA $219 per night from Jul 5 to Jul 6
CA $219
per night
Jul 5 - Jul 6
Book a stay at this beach motel in Lunenburg. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...
Atlantic View Motel and Cottages
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 ...
9.6/10 Exceptional! (49 reviews)
"Fun accomodation and setting! Love the skylight."

Reviewed on Jun 29, 2026

Black Forest Cabins
Floating Cottage on The LaHave River close to beaches, golf, on Lighthouse Route

Floating Cottage on The LaHave River close to beaches, golf, on Lighthouse Route

Pleasantville NS
Stay at this houseboat in Pleasantville. Enjoy free WiFi, a garden, and patios. Popular attractions DesBrisay Museum and Woodland Gardens are located ...
10/10 Exceptional! (89 reviews)
"Everything was above and beyond our expectations, the property is amazing and every single detail was perfect, sharp knives, 100% cotton bedding and towels, the absolute best tasting tap water amazing,surprises to discover on short outings! Picture perfect views and the best stars at night.We hated ..."

Reviewed on Aug 22, 2025

Floating Cottage on The LaHave River close to beaches, golf, on Lighthouse Route
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

Lunenburg NS
Stay at this cottage in Heckmans Island. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Ironworks Distillery and Heckman-Morash House ...
10/10 Exceptional! (125 reviews)
"I travelled to Cozy Cottage with my partner and his 80 year old mother.The cottage is adorable and very well maintained. It is extremely clean and well stocked. The location is drivable to many enjoyable spots. But when the weather was nice, we preferred to stay right there and enjoy the scenery. ..."

Reviewed on Jun 27, 2026

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
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.

Stay near popular Chester attractions

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