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 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.

Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
49 North St Bridgewater NS
The price is ¥20,779 per night from Oct 4 to Oct 5
¥20,779
¥25,130 total
Oct 4 - Oct 5
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! (1,013 reviews)
"Nice clean hotel with friendly staff."

Reviewed on Sep 7, 2026

Travelodge by Wyndham Bridgewater
Bridgewater Hotel

Bridgewater Hotel

2.5 out of 5
35 High St. Bridgewater NS
The price is ¥14,568 per night from Sep 8 to Sep 9
¥14,568
¥17,106 total
Sep 8 - Sep 9
includes taxes & fees
Stay at this hotel in Bridgewater. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
6/10 (502 reviews)
"Room was clean. Staff was friendly. Would go again."

Reviewed on Sep 7, 2026

Bridgewater Hotel
Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
Fully refundableReserve now, pay when you stay
The price is ¥30,008 per night from Sep 20 to Sep 21
¥30,008
¥34,210 total
Sep 20 - Sep 21
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 Valverde ...
8.2/10 Very Good! (580 reviews)
"rooms are clean and modern updates. restaurant could be better as the food was just below average."

Reviewed on Sep 7, 2026

Oak Island Resort & Conference 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.
Oakhill Pines Campground

Oakhill Pines Campground

3 out of 5
388 Oakhill Rd Oak Hill NS
Stay at this cabin in Oakhill. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Osprey Ridge Golf Course and Bridgewater Mall are located ...
8.8/10 Excellent! (33 reviews)
"We booked one of the cabins due to rain. The cabin was very clean and comfortable and very close to the bathrooms, showers and swimming pool. The bed was very cozy, not cheap plastic and foam but an actual memory foam mattress!"

Reviewed on Sep 7, 2026

Oakhill Pines Campground
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 Suttles ...
9.6/10 Exceptional! (75 reviews)
"Nice staff with prompt response. However, garbage bin in the cabin was not emptied before our stay."

Reviewed on Sep 2, 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! (96 reviews)
"The floating cottage was thoughtfully designed, beautifully decorated, well provisioned, and has everything one would need for a private and cozy stay. We loved the many windows that we kept open to hear the sound of the water and nature. The host provided many extra amenities for the guests including ..."

Reviewed on Sep 4, 2026

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