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 S$202 per night from 12 Jul to 13 Jul
S$202
12 Jul - 13 Jul
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 their ...
8/10 Very good! (977 reviews)
"The staff at the reception helped us very much and was very kind! The bathroom was one of the cleanest ones we've seen even though the hotel isn't new."

Reviewed on 5 Jul, 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 S$245 per night from 4 Aug to 5 Aug
S$245
4 Aug - 5 Aug
includes taxes & fees
Stay at this business-friendly hotel in Western Shore. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Oak Island and Tancook Island ...
8.2/10 Very good! (512 reviews)
"Beautiful location and facility. Restaurant hours inconvenient for our purpose. A used facecloth was left behind on bathroom floor."

Reviewed on 2 Jul, 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
Fully refundableReserve now, pay when you stay
The price is S$237 per night from 9 Jul to 10 Jul
S$237
9 Jul - 10 Jul
includes taxes & fees
Stay at this beach motel in Lunenburg. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the helpful staff in their reviews. Popular attractions ...
9/10 Wonderful! (609 reviews)
"Really enjoyed our stay."

Reviewed on 5 Jul, 2026

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
Stay at this spa cabin in Mahone Bay. Enjoy free Wi-Fi, free parking and a full-service spa. Popular attractions Mahone Bay Swimming Pool and Have A Yarn are ...
9.6/10 Exceptional! (52 reviews)
"The room was gorgeous in every detail, the owners have a great sense of style and they know how to create a comfortable experience. The location was great for convenience, shops and food in a nice little town, especially if you’re driving from Peggy’s Cove, stopping in Mahone Bay, then on to Lunenburg ..."

Reviewed on 3 Jul, 2026

Black Forest Cabins
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