Chester Vacations from $621

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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!

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Sandman Signature Dartmouth Hotel & Suites
Nalu Retreat & Nordic Spa
Hearthstone Inn Boutique Hotel Halifax - Dartmouth
The Sutton Place Hotel Halifax
Brewery Park Hotel
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Discover the most popular places to visit in Chester

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
$107 nightly
The price is $125 total per night from Jan 14 to Jan 15
$125 total
Jan 14 - Jan 15
Total with taxes and fees
8/10 Very Good! (917 reviews)
Room had all the necessities and was fresh and clean. Staff was very courteous and helpful. Enjoyed the breakfast. We plan to stay again.

Reviewed on Dec 15, 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
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $130 total per night from Jan 18 to Jan 19
$130 total
Jan 18 - Jan 19
Total with taxes and fees
9.2/10 Wonderful! (1,006 reviews)
Cleanliness

Reviewed on Dec 30, 2025

Best Western Plus Bridgewater Hotel & Convention Centre
Brigantine Inn & Suites

Brigantine Inn & Suites

3 out of 5
82 Montague Street Lunenburg NS
8/10 Very Good! (579 reviews)
Adorable rooms

Reviewed on Nov 23, 2025

Brigantine Inn & Suites
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.

Find the Best Chester Vacation Packages

Things to do in and around Chester

Chester, Nova Scotia, is perfect for outdoor family vacations, offering a variety of activities like scenic boardwalk strolls, golfing, and enjoying the beautiful beaches. Visitors can explore nature trails and embark on outdoor adventures, making it an ideal destination for those seeking fun in the sun and memorable tours. Whether you're looking for relaxation or excitement, Chester provides a delightful blend of experiences for everyone.

Shopping

For a delightful shopping experience in Chester, visit For The Birds Nature Shop, located 9 miles away, for unique gifts. If you're up for a drive, check out Have A Yarn and Northern Sun Gallery & Gifts, both 10 miles away, offering charming items perfect for souvenirs.

Recreation

Explore Graves Island Provincial Park, just 2 miles from Chester, where you can unwind in nature's embrace and enjoy serene walks. For entertainment, visit the Chester Playhouse, a charming theater offering cultural performances perfect for a romantic evening. Don’t forget to hit the Chester Golf Club for an invigorating round of golf.

Adventure

Hit the slopes at Ski Martock, a thrilling ski field located 27 miles from Chester, where you can enjoy exhilarating skiing and snowboarding. For a different adventure, zipline through the trees at Ontree Fun and Adventure Park, also 27 miles away, offering an exciting outdoor experience.

Nightlife

Chester's nightlife features cozy pubs and vibrant music venues. Visit The Kiwi Cafe for great food and local brews, or enjoy live performances at the Chester Playhouse. The friendly atmosphere and beautiful waterfront views make for an unforgettable evening in this charming coastal town.

*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 outdoor and family beach vacations. Visitors can enjoy a variety of attractions including beautiful lakes, scenic islands, and pristine beaches, making it perfect for those seeking outdoor adventures and picturesque views. When exploring Chester, you'll find plenty of opportunities for relaxation and recreation by the water, ensuring a memorable getaway for travelers of all ages.

  • Oak Island: Located 3 miles from Chester, Oak Island is famous for its intriguing history and legends of buried treasure. Visitors can enjoy beautiful beaches and outdoor activities, making it a perfect spot for exploration and relaxation amidst stunning natural scenery.
  • Chester Art Center: Situated in the heart of Chester, this vibrant gallery showcases local art and culture. It offers a variety of exhibitions and workshops, allowing visitors to immerse themselves in the creative spirit of the community.
  • Bayswater Beach Provincial Park: About 9 miles away from Chester, this picturesque beach features soft sands and scenic views. Ideal for swimming, picnicking, or simply soaking up the sun, it provides a tranquil escape for nature lovers.

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

  • 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 to Chester during the low season (March and December to January) for more affordable options.
  • 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.

Chester Essential Information

Language
English
Currency
Canadian dollars
Population
1,550
Max Temp Winter
35ºF
Max Temp Summer
70ºF
Top Sights
Bayswater Beach Provincial Park, Chester Playhouse and Lordly House Museum

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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from $621 on Expedia for your Chester getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
November, December and January are great times to look for cheap Chester vacation packages. Traveling in less busy periods means you'll typically find better prices on accommodations and flights.
How many days is enough for Chester?
When planning your Chester vacation, a few days will be enough to explore all the highlights. Be sure to stop by Chester Golf Club — it's one of the top sights in this destination. If you want more adventure, consider basing yourself here and going on some trips from Chester.
Is it worth booking a vacation package to Chester?
From cool attractions such as Chester Golf Club and Graves Island Provincial Park to its epic watersports, a Chester vacation is sure to exceed your expectations. With so much to see and do, find out for yourself why Chester is such a good vacation destination.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Chester package deal right away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chester escape underway.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester getaway by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to see some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chester?
If you're planning a spur-of-the-moment Chester getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Chester trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.

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