Chester

Travel Guide

Chester
Chester
Chester
Chester
Chester
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.

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
The price is ¥20,431 per night from Jun 14 to Jun 15
¥20,431
¥23,291 total
Jun 14 - Jun 15
includes taxes & fees
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! (501 reviews)
"Property was clean and well maintained. We enjoyed our 1 night stay."

Reviewed on Jun 7, 2026

Oak Island Resort & Conference Centre
The Homeport Motel

The Homeport Motel

2 out of 5
167 Victoria Road Lunenburg NS
The price is ¥20,095 per night from Jun 9 to Jun 10
¥20,095
¥22,908 total
Jun 9 - Jun 10
includes taxes & fees
Stay at this motel in Lunenburg. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9/10 Wonderful! (612 reviews)
"Quick arrival. They sent code and room number by email Had all the basic kitchen things you needed Tha chairs in the kitchen area aren’t very comfortable The beds were very comfortable Good value"

Reviewed on Jun 8, 2026

The Homeport Motel
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 ¥23,921 per night from Jun 14 to Jun 15
¥23,921
¥27,270 total
Jun 14 - Jun 15
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! (1,015 reviews)
"We love coming here for some family fun. The staff are great, kids love the pool and breakfast is well managed. It’s a great spot to break up your winter."

Reviewed on Jun 8, 2026

Best Western Plus Bridgewater Hotel & Convention Centre
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! (39 reviews)
"I loved this little cabin in the woods as well as the area it's in. The is a quaint little village about 3 minutes away. I would definitely come back ☺️"

Reviewed on Jun 7, 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
Luxury lakefront dome with private beach, close to nature and town!

Luxury lakefront dome with private beach, close to nature and town!

Lunenburg NS
Book a stay at this golf apartment in Pine Grove. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Osprey Ridge Golf Course and Bridgewater ...
10/10 Exceptional! (16 reviews)
"This property exceeded our expectations! We were a tad apprehensive about staying in a dome, but it was amazing! It was right next to the lake, which was beautiful. We were so very impressed with the detail that was put into making this property perfect! Loved it!!"

Reviewed on May 29, 2026

Luxury lakefront dome with private beach, close to nature and town!
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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