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.
Mamas by the sea B&B
South West Mermaid Inn
Brier Island Lodge
Liscombe Lodge Resort and Conference Centre
Claymore inn & Suites

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?

 

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Chester Hotel Deals

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Jun 14 to Jun 15
CA $209
CA $238 total
Jun 14 - Jun 15
includes taxes & fees
8.2/10 Very Good! (497 reviews)
"The hotel was excellent. The dinner and breakfast we had was exceptional. Best dinner we had in a long time. Overall a great place and highly recommend."

Reviewed on Jun 3, 2026

Oak Island Resort & Conference Centre
The Homeport Motel

The Homeport Motel

2 out of 5
167 Victoria Road Lunenburg NS
The price is CA $164 per night from Jun 8 to Jun 9
CA $164
CA $187 total
Jun 8 - Jun 9
includes taxes & fees
9.2/10 Wonderful! (605 reviews)
"Great place to stay when you’re in Nova Scotia"

Reviewed on Jun 3, 2026

The Homeport Motel
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 $208 per night from Jun 7 to Jun 8
CA $208
CA $237 total
Jun 7 - Jun 8
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Wonderful with 3 kids under 3 . Great pool and breakfast! Very clean"

Reviewed on Jun 2, 2026

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.

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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.