Chester Vacation Packages

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Your Chester Vacation

Take the hassle out of travel planning with a Chester vacation package. A great neighborhood to base yourself in this captivating city is Garden Lots, which is good for watersports and much more. A trip to Chester is a superb opportunity to sightsee. Be sure to visit well-known attractions like Oak Island, Tancook Island and Chester Golf Club. Stop dreaming and start traveling. Browse the wide range of options on Expedia today and finally put your Chester vacation plans into action!

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hearthstone Inn Boutique Hotel Halifax - Dartmouth
Sandman Signature Dartmouth Hotel & Suites
Coastal Inn Halifax
Red George Inn and Suites
Chateau Bedford, Trademark Collection by Wyndham

Things to do in and around Chester

Chester, Nova Scotia, is perfect for outdoor family vacations, featuring a scenic boardwalk and excellent golf courses. Visitors can enjoy memorable golf vacations, explore nearby attractions, and indulge in beach activities. The charming shops provide a delightful browsing experience, making Chester a wonderful destination for those seeking relaxation and adventure in a picturesque coastal setting.

Shopping

In Chester, you can visit Northern Sun Gallery & Gifts for unique items. If you're up for a drive, the Hubbards Farmer's Market offers local produce and crafts, while the Bridgewater Mall features a variety of shops and entertainment, located 29.0km away. Enjoy your shopping adventure.

Recreation

At Graves Island Provincial Park, immerse yourself in nature's tranquility, enjoying serene walks and beautiful views. Meanwhile, the Chester Playhouse offers a delightful cultural experience with engaging performances, perfect for a family night out. For sports enthusiasts, the Chester Golf Club provides an invigorating outdoor atmosphere with stunning landscapes.

Adventure

Experience the thrills of Ski Martock, a ski field 43.5km from Chester, where you can enjoy skiing and embrace the sporty atmosphere. For an exhilarating adventure, head to Ontree Fun and Adventure Park, also 43.5km away, offering a fantastic zipline and ropes course surrounded by nature.

Nightlife

Chester offers a charming nightlife with cozy spots like the Chester Playhouse for local performances and the Kiwi Café for a laid-back meal. For a lively evening, enjoy a drink at the nearby Oceanstone Seaside Resort, where you can soak in the coastal ambiance under the stars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Chester

Chester, Nova Scotia, is an ideal destination for families seeking outdoor and beach vacations. With its picturesque lakes, charming islands, and beautiful beaches, visitors can enjoy a variety of scenic experiences. Explore top attractions that highlight the area's natural beauty, perfect for those looking to relax by the water or engage in outdoor activities. Whether you're with family or friends, Chester offers a delightful getaway filled with adventure and tranquility.

  • Oak Island: A short 4.8km journey from Chester, Oak Island offers stunning beaches and an inviting outdoor atmosphere. Explore the intriguing legends surrounding the island, including the famous treasure hunt that has captivated adventurers for centuries.
  • Lordly House Museum: Located in the heart of Chester, this museum showcases the rich cultural history of the area. Wander through its exhibits to gain insight into the local heritage and enjoy the charming architecture of this historic site.
  • Bayswater Beach Provincial Park: Situated 14.5km from Chester, this picturesque beach park provides a serene escape with beautiful sandy shores and tranquil waters, perfect for a relaxing day by the sea.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in August, when visitor numbers are high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in February, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.4°F (-2.0°C)Light RainMostly CloudyAverageSlightly Low
February27.5°F (-2.5°C)Light RainMostly CloudyAverageAverage
March32.0°F (0.0°C)Light RainMostly CloudyAverageSlightly Low
April40.3°F (4.6°C)Light RainMostly CloudyAverageAverage
May48.4°F (9.1°C)Light RainMostly CloudyAverageAverage
June56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
July64.8°F (18.2°C)Light RainMostly SunnyHighSlightly High
August66.4°F (19.1°C)Light RainMostly SunnyHighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyHighSlightly High
October52.5°F (11.4°C)Light RainMostly SunnyLowAverage
November43.0°F (6.1°C)Light RainMostly CloudyLowAverage
December34.9°F (1.6°C)Light RainMostly CloudyLowSlightly Low

Tips to save on your trip to Chester

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically March and December to January) for more affordable package holidays to Chester.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Ready to book your vacation to Chester?

 

Choose your dates

Chester Hotel Deals

Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
49 North St Bridgewater NS
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Jul 28 to Jul 29
CA $184
CA $223 total
Jul 28 - Jul 29
includes taxes & fees
8/10 Very good! (995 reviews)
"Very dissapointed. Could not stay. The staff were very friendly. However the whole place is very dated and our room smelled very strongly with an unpleasant odour."

Reviewed on Jul 16, 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
The price is CA $235 per night from Jul 19 to Jul 20
CA $235
CA $268 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (625 reviews)
"Look, great location for us but it is what it is, nice clean place to spend the night with access to the ocean Room are very clean and well put together, the extras were a great surprise and the bed was comfortable I do recommend"

Reviewed on Jul 18, 2026

Atlantic View Motel and Cottages
Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

3.5 out of 5
527 Highway 10 Exit 12 Cookville NS
Fully refundableReserve now, pay when you stay
The price is CA $280 per night from Jul 19 to Jul 20
CA $280
CA $319 total
Jul 19 - Jul 20
includes taxes & fees
Best Western Plus Bridgewater Hotel & Convention 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.

Stay near popular Chester attractions

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this destination from CA $547 on Expedia. But how much your vacation to Chester costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chester?
The off-season is the best time to head to Chester if you're trying to save. Another tip for getting cheap Chester vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Chester?
For your Chester vacation, a handful of days will be enough to see the top spots. Be sure to stop by Tancook Island — it's one of the most popular sights in this destination. If you want more adventure, think about basing yourself here and setting off on some trips from Chester.
Is it worth booking a vacation package to Chester?
Boasting a host of highlights starting with its amazing watersports, Chester is a good vacation destination. Whether you'd like to visit attractions such as Chester Golf Club and Tancook Island or venture off the beaten track, you'll have loads to keep you busy during your Chester vacation.
How to find the best Chester package deals?
Begin your search for a Chester package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Chester package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester getaway off to a flying start.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your next Chester getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chester?
Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Chester escape.
How to plan a trip to Chester?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite season and the available activities will also help you decide when to escape to Chester.
  2. Set your budget: Consider expenses like flights, transportation and food when calculating how much to set aside for your trip to Chester. Then, pick a property that works with your budget, whether that's an economical stay or a swankier retreat.
  3. Decide how long to go away for: Now that you're up to speed on Chester, you can figure out the right length of your break. Create a rough plan and give yourself enough time for all the things you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Chester vacation package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.