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
$136 nightly
The price is $160 total per night from Aug 30 to Aug 31
$160 total
Aug 30 - Aug 31
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! (1,020 reviews)
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Reviewed on Aug 8, 2026

Travelodge by Wyndham Bridgewater
Bridgewater Hotel

Bridgewater Hotel

2.5 out of 5
35 High St. Bridgewater NS
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $116 total per night from Aug 25 to Aug 26
$116 total
Aug 25 - Aug 26
Total with taxes and 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 (462 reviews)
"The bathroom and the tub were not clean. The bath towels were smelling… not sure if they were fresh."

Reviewed on Aug 10, 2026

Bridgewater Hotel
Atlantic View Motel and Cottages

Atlantic View Motel and Cottages

3 out of 5
230 Mason's Beach Road, RR#2 Lunenburg NS
$186 nightly
The price is $212 total per night from Aug 13 to Aug 14
$212 total
Aug 13 - Aug 14
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! (651 reviews)
"Everything was excellent!"

Reviewed on Aug 8, 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
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! (66 reviews)
"Beautiful architecture. Cute stylish cabins in a great location. Very walkable. Was told we would get check in instructions 24 hours in advance. We didn’t receive them till that morning. Later I wanted to report an issue we were having. I sent two text messages through their website link and QR code. ..."

Reviewed on Aug 9, 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! (91 reviews)
"This property is even nicer in real life. The cottage is very clean and neat, the setting is absolutely gorgeous, and the host has thought of every amenity. An ideal place to unplug and reconnect with nature."

Reviewed on Jul 16, 2026

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! (130 reviews)
"Great family orientated vacation spot. Our kids enjoyed the dvd collection on the rainy evenings and the kayaks on the sunny days. We all loved the deck and stocked fire pit. Close to Lunenburg’s restaurants and shopping but far enough away to escape the crowds. Great communication from the property ..."

Reviewed on Aug 9, 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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