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.

Bridgewater Hotel

Bridgewater Hotel

2.5 out of 5
35 High St. Bridgewater NS
$84 nightly
The price is $99 total per night from Oct 17 to Oct 18
$99 total
Oct 17 - Oct 18
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 (527 reviews)
"Nothing really special but great if you need a place to stay"

Reviewed on Sep 24, 2026

Bridgewater Hotel
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 Oct 13 to Oct 14
$157 total
Oct 13 - Oct 14
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! (1,003 reviews)
"Had a great laugh (happy) cry with front desk staff. Welcomed our dogs with open arms."

Reviewed on Sep 24, 2026

Travelodge by Wyndham Bridgewater
Days Inn & Conference Center by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater

2.5 out of 5
50 North Street Bridgewater NS
$123 nightly
The price is $144 total per night from Oct 21 to Oct 22
$144 total
Oct 21 - Oct 22
Total with taxes and fees
Book a stay at this business-friendly hotel in Bridgewater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,004 reviews)
"Exactly as expected. Pay attention to the breakfast times as they are different (a bit later) on the weekends. We were a few minutes late on Monday and we had to settle for a muffin and a banana."

Reviewed on Sep 24, 2026

Days Inn & Conference Center by Wyndham Bridgewater
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 Lordly House Museum and Valverde Studio Gallery are ...
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 Suttles ...
Black Forest Cabins
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! (37 reviews)
"What can I say, we were EXTREMELY late because of the CAT and the host was very kind and gracious by waiting for us to arrive after hours. It meant a lot since we had been traveling all day and the thought of sleeping in our car wasn’t something I wanted."

Reviewed on Sep 20, 2026

Oakhill Pines Campground
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

Frequently asked questions

Is Chester worth visiting?
Chester is worth visiting for its standout attractions, including the scenic Tancook Island and the recreational opportunities at Chester Golf Club. Travelers also have access to local grocers, making self-catering convenient for their stay.
When is the best time to visit Chester?
The best time to visit Chester is from July through September, when the weather is typically mild and enjoyable for exploring. For travelers seeking fewer crowds and better value, the quieter months of October through December offer a more relaxed experience.
What is Chester known for?
Chester is known for Tancook Island. Travelers can also enjoy a round at the Chester Golf Club and catch performances at the Chester Playhouse. These institutions offer travelers a variety of experiences in Chester.
What is a good itinerary length for Chester?
A good itinerary length for Chester is one to two days to enjoy the Chester Golf Club or catch a show at the Chester Playhouse. For a longer trip of three to four days, travelers can also explore Tancook Island and savor local seafood, Italian, or Middle Eastern cuisine.
What are the top things to do in and around Chester?
Chester offers a mix of island exploration, cultural venues, and outdoor recreation for travelers:


How do I plan a trip to Chester?
To plan your trip to Chester, book flights, hotels, and a rental car in advance, especially during popular times. Consider activities like visiting Tancook Island, playing at Chester Golf Club, or seeing a show at Chester Playhouse. When planning outdoor excursions, always have indoor alternatives ready for weather flexibility.
Can I book a refundable hotel in Chester?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chester by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chester with Expedia?
Expedia makes it easier to plan your Chester trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chester?
The best choice depends on your travel style. Hotels in Chester can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chester trip on Expedia?
Once you've booked your Chester trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chester trip?
Expedia offers customer support before, during, and after your Chester trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chester?
If it's your first trip to Chester, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chester hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chester hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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