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
$134 nightly
The price is $157 total per night from Jul 14 to Jul 15
$157 total
Jul 14 - Jul 15
Total with taxes and 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! (987 reviews)
"Enjoyed our stay here."

Reviewed on Jul 11, 2026

Travelodge by Wyndham Bridgewater
Atlantic View Motel and Cottages

Atlantic View Motel and Cottages

3 out of 5
230 Mason's Beach Road, RR#2 Lunenburg NS
$173 nightly
The price is $198 total per night from Jul 15 to Jul 16
$198 total
Jul 15 - Jul 16
Total with taxes and fees
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 ...
9/10 Wonderful! (617 reviews)
"Belle déco, bien aménagé et rénové"

Reviewed on Jul 8, 2026

Atlantic View Motel and Cottages
Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
$164 nightly
The price is $187 total per night from Aug 10 to Aug 11
$187 total
Aug 10 - Aug 11
Total with taxes and 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! (517 reviews)
"Beautiful views. Very private with lots to do on site."

Reviewed on Jul 11, 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.
Chester Back Harbour Exclusive providing direct access to water via private dock

Chester Back Harbour Exclusive providing direct access to water via private dock

Chester Basin NS
Stay at this vacation home in Chester. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Tancook Island and Lordly House Museum are located ...
Chester Back Harbour Exclusive providing direct access to water via private dock
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! (53 reviews)
"Spacious, quiet cabin getaway minutes from Mahone Bay and close to Lunenburg! We enjoyed our stay at the Black Forest Cabins—we had everything we needed and thoroughly enjoyed the spa-like bathroom in our cabin. Wish we would have had time to check out the sauna, but we were only there for one night ..."

Reviewed on Jul 8, 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! (90 reviews)
"What a beautiful stay this was. The place is idyllic and one of the best places we’ve ever had. Everything you could need is provided. Everything is clean, comfortable and so well thought through. We really didn’t want to leave. Gordan, the host is great with communications and information. He’s ..."

Reviewed on Jul 9, 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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