Chester Holidays from AU$552
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Your Chester Holiday
Select a Chester holiday package and concentrate on what's important — having fun. There's no more planning nightmares, just a lot more time to uncover the best of this awesome city, such as its rich history and cultural experiences. Swarthmore College, Harrahs Casino and Racetrack and Widener University are just a few of the many attractions you'll want to check out during your trip to Chester. Whoever you're travelling with and whatever your bank balance, your ultimate Chester holiday is just a few clicks away with Expedia.
The Latest Chester Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Rittenhouse Philadelphia
Center City
AU$1,406
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
Boston (BOS) to Philadelphia (PHL)
9.6/10 Exceptional! (1,010 reviews)
The front entrance smelled like a porta potty. I raised this to the staff but they didn’t seem to smell it.
Reviewed on 3 Sept 2026
Hyatt Centric Rittenhouse Square Philadelphia
Center City
AU$873
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
Boston (BOS) to Philadelphia (PHL)
9.4/10 Exceptional! (1,742 reviews)
I enjoyed my two-night stay at the Hyatt Centric. My room was ready upon check-in and was in pristine condition. Staff was friendly and professional, the hotel was quiet, and I had a lovely view from my room. The hotel is centrally located and close to restaurants, stores, and public transportation; it is also one mile from attractions like Reading Terminal Market.
One thing to note: the entrance to the hotel is on a side street, which I almost missed because I was not expecting it. This has nothing to do with the service of the hotel, but is something to be aware of (I walked to the hotel at nearly midnight and felt perfectly safe).
Overall, I would recommend this hotel for a getaway to (or staycation in!) Philly.
Reviewed on 4 Sept 2026
One Sky Loft
Center City
AU$763
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
Boston (BOS) to Philadelphia (PHL)
9.4/10 Exceptional! (129 reviews)
Check in was very difficult, did not receive code to get in the room until trying to call the number for over half an hour. Once connected, got disconnected and couldn’t reach again until another 20 minutes. However, once in the room it was very nice.
Right before check out, noticed a huge amount of mold and fungus growing out of the main AC air vent. Alerted the owner of this as my wife was pregnant and it was very concerning to have been breathing that, but did not receive a waiver of any kind as a result.
Very nice place outside the significant amount of mold and disappointing communication/service.
Reviewed on 4 Sept 2026
Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City
Center City
AU$858
per person
12 Nov - 15 Nov
found 1 day ago
Return flight included
Boston (BOS) to Philadelphia (PHL)
8.8/10 Excellent! (1,451 reviews)
Perfect place to stay. Staff was great, walking distance to everything. Only complaint was breakfast wasn’t very good.
Reviewed on 4 Sept 2026
Chester Holiday
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Philadelphia Intl. Airport (PHL) |
Population | 34,100 |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Philadelphia Museum of Art, Philadelphia Zoo and Mann Centre for the Performing Arts |
Our pick of the best Chester Hotel Deals
Comfort Inn Philadelphia International Airport West
1300 Providence Ave Chester PA
Fully refundable
AU$130
14 Sept - 15 Sept
includes taxes & fees
Club Quarters Hotel Rittenhouse Square, Philadelphia
1628 Chestnut St Philadelphia PA
Fully refundableReserve now, pay when you stay
AU$225
10 Sept - 11 Sept
includes taxes & fees
The Windsor Suites
1700 Ben Franklin Pkwy Philadelphia PA
Fully refundableReserve now, pay when you stay
AU$156
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (3,203 reviews)
"Large rooms, large bathrooms, bath tub was SUPER Slippery. Very outdated infrastructure inside, ac couldn’t cool the room below 75 degrees"
Reviewed on 4 Sept 2026
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 City Hall
7.8/10 (23 reviews)
Chester City Hall stands as the administrative heart of one of Pennsylvania's oldest cities. Visitors can explore its architecture and learn about local governance during regular business hours.
Subaru Park
7.0/10 (40 reviews)
Subaru Park nestles along the Delaware River, providing intimate views of Union matches beneath the Commodore Barry Bridge. Evening games showcase stunning sunsets while passionate supporters create an electric atmosphere.
Harrah's Casino and Racetrack
7.6/10 (114 reviews)
Why not roll the dice with a visit to Harrah's Casino and Racetrack during your travels in Chester? Experience the acclaimed art galleries or attend a sporting event in this family-friendly area.
WSFS Bank Sportsplex
Catch an event at WSFS Bank Sportsplex during your trip to Chester. Visit the casinos in this family-friendly area or simply enjoy its restaurants.
The Block Event Center at Harrahs Philadelphia
After visiting The Block Event Center at Harrahs Philadelphia, make a plan to see the other sights and activities in Chester. Visit the casinos in this family-friendly area or simply enjoy its restaurants.
South Chester Market Place
This community marketplace offers a welcoming atmosphere with unique local vendors selling everything from clothing to housewares. Browse artisan goods and savour generous portions of soul food in the vibrant food court.
Crozier Park
Crozer Park offers a tranquil urban retreat with lush greenery and well-maintained walking paths. Visitors can escape city life with a peaceful morning stroll or invigorating run through its scenic surroundings.
Ethel Waters Park
This waterfront park honours Chester native Ethel Waters, a legendary jazz and blues vocalist. Enjoy peaceful river views while community events like Tuesday evening dance sessions bring the space to life.
What to do in Chester
LEGOLAND® Discovery Center Philadelphia
AU$35
per adult
80% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
AU$82
per adult
82% of travellers recommend
Double Decker Hop-On Hop-Off City Sightseeing Philadelphia (1, 2, or 3-Day)
AU$68
per adult
90% of travellers recommend
Frequently asked questions
How much does a Chester holiday package cost?
You'll find cheap prices from AU$552 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?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
