Chester Vacations from $443

Book a Hotel + Flight or Car together to unlock savings

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.
Tru By Hilton Yarmouth
The Sutton Place Hotel Halifax
Lux Exec Home HFX Waterfront Pool Hot Tub
Cambridge Suites Hotel
Brewery Park Hotel
Don't see what you're looking for?
See all available trips from Columbus to Chester
View all trips

Discover the most popular places to visit in Chester

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
$138 nightly
The price is $162 total per night from Aug 24 to Aug 25
$162 total
Aug 24 - Aug 25
Total includes taxes and fees
8/10 Very Good! (781 reviews)
"Most everything was in walking distance of the property."

Reviewed on Aug 16, 2025

Travelodge by Wyndham Bridgewater
Miller House By the Bay

Miller House By the Bay

2 out of 5
624 Main street, mahone bay, NS
$111 nightly
The price is $127 total per night from Sep 6 to Sep 7
$127 total
Sep 6 - Sep 7
Total includes taxes and fees
9.4/10 Exceptional! (53 reviews)
"Excellent breakfast and friendly atmosphere"

Reviewed on Aug 16, 2025

Miller House By the Bay
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.

Things to do in and around Chester

Chester, Nova Scotia, is perfect for outdoor and family vacations, featuring a variety of activities such as shopping at local centers and enjoying golf. Visitors can indulge in beach vacations, guided tours, and a range of outdoor adventures. Nature trails offer opportunities for exploration and outdoor fun, making Chester an ideal destination for those seeking a blend of relaxation and adventure.

Shopping

In Chester, you can visit Have A Yarn, a charming store located 10 miles away, and For The Birds Nature Shop, just 9 miles from town. If you're up for a drive, the Bridgewater Mall, 18 miles away, offers a vibrant shopping experience with entertainment and dining options.

Recreation

Experience tranquility at Graves Island Provincial Park, just 2 miles from Chester, where nature invites relaxation. Enjoy cultural performances at the Chester Playhouse, perfect for family entertainment and romance. For sports enthusiasts, the Chester Golf Club offers a scenic outdoor setting to enjoy a round of golf.

Adventure

Hit the slopes at Ski Martock, located 27 miles from Chester, where you can enjoy skiing and snowboarding amidst thrilling sports vibes. For a different kind of excitement, head to Ontree Fun and Adventure Park, also 27 miles away, to tackle zip lines and rope courses in a vibrant outdoor setting.

Nightlife

Chester's nightlife features a charming atmosphere with cozy pubs and vibrant live music. Visit The Rope Loft for fresh seafood and cocktails, or check out the local talent at the Chester Playhouse. Enjoy captivating waterfront views while unwinding with friends in this picturesque 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 perfect for outdoor and family vacations, offering a blend of scenic lakes, charming islands, and beautiful beaches. Visitors can explore the picturesque surroundings and enjoy various recreational activities that cater to beach lovers and nature enthusiasts alike. Don't miss the chance to discover the unique charm of Chester and its stunning landscapes, making it an ideal destination for a memorable getaway.

  • Oak Island: Located 3 miles from Chester, Oak Island offers a stunning beach and outdoor setting. Known for its intriguing treasure hunt history, visitors can enjoy sunbathing, hiking, and exploring the island's natural beauty while soaking in the fresh ocean air.
  • Amicus Gallery: Nestled in the heart of Chester, Amicus Gallery showcases local art and culture. The gallery features a rotating collection of works from regional artists, providing a unique opportunity to immerse yourself in the creative spirit of the area.
  • St. Stephen's Church: This historic church, situated in Chester, is a beautiful example of local architecture. Visitors can appreciate its serene atmosphere and rich cultural significance, making it a perfect spot for reflection and appreciation of the community's heritage.

Best time to go to Chester

The best time to visit Chester is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. February is its coolest month on average. At this time, 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

  • 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.

More vacations you might like

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from $443 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.