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

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

CA $751
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
7.2/10 Good! (1,285 reviews)
Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Save 100% on your flight
CA $1,897
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9.8/10 Exceptional! (8 reviews)
Everything was unique especially the automated system. Enjoyed the spa. We had some difficulty using the living room tv. Could not find local channels. Everything was LG channels. Otherwise the location, decor and amenities was extraordinary. We will tell our friends about this wonderful place.

Reviewed on Oct 5, 2026

Brewery Park Hotel

Brewery Park Hotel

North End
CA $1,209
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9/10 Wonderful! (286 reviews)
Seasons Inn Halifax

Seasons Inn Halifax

Fairview
CA $828
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
6.8/10 (1,022 reviews)
Couldn’t pay me to stay here again

Reviewed on Oct 6, 2026

The Lord Nelson Hotel & Suites

The Lord Nelson Hotel & Suites

Downtown Halifax
CA $895
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9.2/10 Wonderful! (2,676 reviews)
This is very nice hotel in the old building. It was another experience to stay in this hotel.

Reviewed on Oct 7, 2026

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

Bridgewater Hotel

Bridgewater Hotel

35 High St. Bridgewater NS
Fully refundableReserve now, pay when you stay
CA $109
CA $128 total
Nov 1 - Nov 2
includes taxes & fees
Bridgewater Hotel
Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

527 Highway 10 Exit 12 Cookville NS
Fully refundableReserve now, pay when you stay
CA $167
CA $191 total
Nov 1 - Nov 2
includes taxes & fees
Best Western Plus Bridgewater Hotel & Convention Centre
Days Inn & Conference Center by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater

50 North Street Bridgewater NS
Fully refundableReserve now, pay when you stay
CA $149
CA $175 total
Nov 1 - Nov 2
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Unfortunately the room we stayed was not worth the $270 (including fees) ... The room was out of the 80's ...needs a lot of updating for that price ... Especially since it was a small town and not a metropolis ... Will not be returning there ..."

Reviewed on Oct 7, 2026

Days Inn & Conference Center by Wyndham Bridgewater
See all 323 properties in Chester
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

Chester Golf Club

8.4/10 (28 reviews)
Enjoy a round of golf in Chester at Chester Golf Club. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants.
See properties

Chester Playhouse

8.6/10 (12 reviews)
You can enjoy a show at Chester Playhouse during your trip to Chester. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants.
See properties

Chester Art Center

8.8/10 (3 reviews)
You can spend an afternoon browsing the exhibits at Chester Art Center during your trip to Chester. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants.
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St. Stephen's Church

9.2/10 (11 reviews)
After visiting St. Stephen's Church, make a plan to see the other sights and activities in Chester. Amble around this family-friendly area's waterfront or experience its entertainment venues.
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Lordly House Museum

8.8/10 (3 reviews)
You can spend time studying the exhibits at Lordly House Museum during your trip to Chester. While in this family-friendly area, you can savor the top-notch restaurants.
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Valverde Studio Gallery

You can spend time exploring the galleries in Valverde Studio Gallery during your trip to Chester. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants.
See properties

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this destination from CA $751 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.

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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.