Chester Holidays

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Chester Holiday

Things to do in and around Chester

Shopping

In Chester, you can enjoy shopping at Wolff's Apple House, just 9.7km away, and Rosie's Farm Market, 14.5km away, both offering vibrant local flavours. If you're up for a drive, Reading Terminal Market is 20.9km away, featuring a lively atmosphere and diverse selections.

Recreation

Experience the vibrant atmosphere at Subaru Park, where you can catch a thrilling sports event. For relaxation, head to Buckley Recreational Field, perfect for unwinding in nature. For some fun and adventure, visit Ice Works Skating Complex, offering ice skating and entertainment just a short distance away.

Adventure

Experience thrilling motor racing at Bridgeport Speedway, located 4.8km from Chester, where the adrenaline rush is palpable. Alternatively, explore the scenic John Heinz Refuge Trails, a hiking trail 4.8km away, offering stunning outdoor views and a true sense of adventure amidst nature.

Nightlife

Chester boasts a vibrant nightlife with a mix of bars and entertainment. Visit the iconic Blue Moon Tavern for a friendly atmosphere and local brews. For dancing, check out The Vault, where you can enjoy live DJs and a lively crowd. Experience Chester's unique charm as the night unfolds.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chester

Chester, Pennsylvania, is perfect for families and those keen on city-themed and outdoor adventures. Explore attractions like the Chester Town Hall, Chester Racecourse, and the picturesque Roman city of Chester. The city's urban parks and neighbourhoods offer a blend of culture and leisure, making it an ideal spot for a memorable holiday. Don't forget to visit Chester Garden for a touch of natural beauty during your stay.

  • Xfinity Mobile Arena: This vibrant arena is located 16.1km from Chester and offers a thrilling atmosphere for live entertainment, from concerts to sports events. With a family-friendly vibe, it’s a perfect spot for enjoying a night out with loved ones.
  • Swarthmore College: Situated 6.4km from Chester, this modern college boasts beautiful grounds and a lively city atmosphere. It's an ideal place to explore art, history, and the academic spirit of a prestigious institution.
  • Please Touch Museum: Located 19.3km away, this engaging children’s museum is filled with interactive exhibits that promote learning through play, making it a delightful experience for families and a great way to immerse in cultural activities.

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 July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January33.3°F (0.7°C)Light RainMostly SunnySlightly LowSlightly Low
February35.6°F (2.0°C)Light RainMostly SunnyAverageSlightly Low
March43.0°F (6.1°C)Light RainMostly SunnyAverageSlightly Low
April53.8°F (12.1°C)Light RainMostly SunnySlightly HighAverage
May63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly High
June72.1°F (22.3°C)Light RainMostly SunnySlightly HighSlightly High
July78.1°F (25.6°C)Light RainMostly SunnySlightly HighAverage
August76.1°F (24.5°C)Light RainMostly SunnyAverageAverage
September69.6°F (20.9°C)Light RainMostly SunnyAverageAverage
October58.6°F (14.8°C)Light RainMostly SunnyAverageSlightly High
November46.8°F (8.2°C)Light RainMostly SunnySlightly LowAverage
December39.2°F (4.0°C)Light RainMostly SunnySlightly LowAverage

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 during the off-peak season (typically January to March) 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.

Our pick of the best Chester Hotel Deals

Comfort Inn Philadelphia International Airport West

Comfort Inn Philadelphia International Airport West

3 out of 5
1300 Providence Ave Chester PA
Fully refundable
The price is NZ$166 per night from 9 Nov to 10 Nov
NZ$166
9 Nov - 10 Nov
includes taxes & fees
7/10 Good! (1,239 reviews)
"This place is a dump not very clean. It’s dated ladybugs were in the room. The bed was uncomfortable. The plaster was old and cracking. The caulking was moldy, not very well kept."

Reviewed on 1 Nov 2026

Comfort Inn Philadelphia International Airport West
Club Quarters Hotel Rittenhouse Square, Philadelphia

Club Quarters Hotel Rittenhouse Square, Philadelphia

4 out of 5
1628 Chestnut St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is NZ$275 per night from 3 Nov to 4 Nov
NZ$275
3 Nov - 4 Nov
includes taxes & fees
9/10 Wonderful! (4,868 reviews)
"Coffee was great, clean"

Reviewed on 1 Nov 2026

Club Quarters Hotel Rittenhouse Square, Philadelphia
Doubletree by Hilton Philadelphia Airport

Doubletree by Hilton Philadelphia Airport

4 out of 5
4509 Island Ave Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 23 Nov to 24 Nov
NZ$202
23 Nov - 24 Nov
includes taxes & fees
8.2/10 Very good! (241 reviews)
"My room wasn’t clean. Very dusty. Coffee stains on dresser, socket coming from the wall, hair and crumbs on bed, lamp was filthy and greasy as if it hadn’t been clean in awhile. Very disappointed"

Reviewed on 1 Nov 2026

Doubletree by Hilton Philadelphia Airport
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

What to do in Chester

Frequently asked questions

How much does a Chester holiday package cost?
You'll find cheap prices on Expedia for your Chester break. However, factors like your choice of hotel, the season and length of stay will influence how much your holiday to Chester costs.
What are the cheapest months to go to Chester?
You can typically find lower rates and better availability in January, February and March. Check out our cheap Chester holiday packages and you could land some excellent off-season deals.
How many days is enough for Chester?
Chester holidays can be short or long, but to get a real feel for this place, we think 2 days is about right. In this timeframe, you can fit in major attractions like Harrah's Casino and Racetrack and Harrah's Casino and Racetrack and seek out some lesser-known gems. Don't miss out on cool neighbourhoods such as Springfield and Collingdale either. If you plan wisely, you may even be able to take a day trip outside of Chester too.
Is it worth booking a holiday package to Chester?
Chester offers everything you need for an unforgettable trip. Begin your Chester holiday on a high note by exploring major attractions like Chester City Hall.
How to find the best Chester package deals?
Landing a cheap Chester package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can personalise your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most affordable Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chester holiday as a package?
You can enjoy significant savings on your next Chester break by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. 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 holiday package to Chester?
Secure incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Chester break.
How to plan a trip to Chester?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Chester.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and food to airfares and activities. Your hotel will likely be the biggest expense during your trip to Chester.
  3. Work out your trip length: Think about how long you want to spend discovering Chester. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chester holiday package that brings all your bookings together.

Explore a world of travel with Expedia

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