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
Sandman Signature Dartmouth Hotel & Suites
Four Points by Sheraton Halifax
Hearthstone Inn Boutique Hotel Halifax - Dartmouth
HFX Airport Hotel

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.

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Chester Hotel Deals

Large, modern Cape Cod style cottage in oceanside charming town

Large, modern Cape Cod style cottage in oceanside charming town

Chester NS
Large, modern Cape Cod style cottage in oceanside charming town
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 $158 per night from Apr 20 to Apr 21
CA $158
CA $181 total
Apr 20 - Apr 21
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
Good

Reviewed on Apr 10, 2026

Best Western Plus Bridgewater Hotel & Convention Centre
Smugglers Cove Inn

Smugglers Cove Inn

4 out of 5
139 Montague Street Lunenburg NS
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Apr 26 to Apr 27
CA $159
CA $182 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (780 reviews)
The owners were very kind and helpful when it came to parking and also recommending things to do in the area. The room was clean and had everything I needed and it was quiet. Great location- there’s a delicious sushi shop and a cafe with great coffee and pastries that you can access in the hotel. ...

Reviewed on Apr 11, 2026

Smugglers Cove Inn
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.

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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.