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.
South West Mermaid Inn
The Barrington Hotel
Lux Exec Home HFX Waterfront Pool Hot Tub
Surfside Inn
Holiday Inn Express & Suites Halifax Airport by IHG

Things to do in and around Chester

Chester, Nova Scotia, offers a delightful mix of outdoor adventures and family-friendly activities. Visitors can enjoy golf vacations, explore nearby attractions, and relax on beautiful beaches. The town also features shopping centres and malls for those looking to browse local shops. With its charming city vibe, Chester is perfect for a memorable getaway filled with leisure and exploration.

Shopping

In Chester, you can shop at Have A Yarn and Northern Sun Gallery & Gifts, both offering unique gifts and souvenirs. If you're up for a drive, visit Bridgewater Mall, located 29.0km away, where you'll find a variety of shops and entertainment options for the whole family.

Recreation

Graves Island Provincial Park offers tranquil nature trails and scenic views, perfect for relaxation and rejuvenation. For a cultural experience, visit Chester Playhouse, where you can enjoy captivating performances in a charming atmosphere. Additionally, the Chester Golf Club invites you to unwind with a round of golf amidst beautiful outdoor settings.

Adventure

Hit the slopes at Ski Martock, located 43.5km from Chester, where you can enjoy thrilling skiing experiences amidst stunning winter landscapes. For a different kind of excitement, visit Ontree Fun and Adventure Park, also 43.5km away, where you can zipline through the trees and conquer ropes courses in a beautiful outdoor setting.

Nightlife

Chester offers a charming nightlife with venues like the Chester Playhouse for live performances and the Kiwi Café for a relaxed bite and drink. For a lively atmosphere, enjoy the local music scene at the Rope Loft, where you can unwind by the water.

*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 the perfect destination for outdoor enthusiasts and families alike, offering a blend of beautiful lakes, scenic islands, and inviting beaches. With a focus on beach and nature experiences, visitors can explore various attractions that highlight the area's stunning scenery. Whether you're seeking relaxation or adventure, Chester provides an array of activities to ensure a memorable vacation in this charming coastal town.

  • Oak Island: Just 4.8km from Chester, Oak Island offers stunning beaches and a relaxed outdoor atmosphere. Explore the island's intriguing history and the legends that surround it, making it a perfect spot for nature lovers and adventure seekers alike.
  • Amicus Gallery: Located in the heart of Chester, Amicus Gallery showcases local art and culture, providing a glimpse into the vibrant artistic community. Enjoy the diverse exhibitions and perhaps meet some of the artists behind the works.
  • St. Stephen's Church: This historic church in Chester is known for its beautiful architecture and serene atmosphere. Take a moment to appreciate the stunning stained glass windows and the rich history that this cherished community landmark represents.

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 with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.4°F (-2.0°C)Light RainMostlyAverageSlightly Low
February27.5°F (-2.5°C)Light RainMostlyAverageAverage
March32.0°F (0.0°C)Light RainMostlyAverageSlightly Low
April40.3°F (4.6°C)Light RainMostlyAverageAverage
May48.4°F (9.1°C)Light RainMostlyAverageAverage
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 RainMostlyLowAverage
December34.9°F (1.6°C)Light RainMostlyLowSlightly Low

Tips to save on your trip to Chester

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chester.
  • 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?

 

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Chester Hotel Deals

Family Home In the Heart of the Village of Chester

Family Home In the Heart of the Village of Chester

Chester
9.4/10 Exceptional! (23 reviews)
Chester Nova Scotia
"This is a great whole home property that offers a lot of easy trip options. There is a super cute small downtown that is a good spot for breakfast / shopping. There is a grocery store super close to the house and the kitchen is well equipped for any meal. The home has no AC but did provide fans. ..."

Reviewed on Jul. 6, 2025

Family Home In the Heart of the Village of Chester
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 $185 per night from Aug 13 to Aug 14
CA $185
CA $224 total
Aug 13 - Aug 14
includes taxes & fees
8/10 Very Good! (740 reviews)
"Always welcoming….."

Reviewed on Jul. 27, 2025

Travelodge by Wyndham Bridgewater
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
The price is CA $238 per night from Aug 24 to Aug 25
CA $238
CA $271 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (920 reviews)
"Josh at front desk was awesome! Super helpful and polite!"

Reviewed on Jul. 29, 2025

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.

Discover the most popular places to visit in Chester

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this destination from CA $546 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.

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