Chester Vacation Packages
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Your Chester Vacation
With one of our vacation packages to Chester, you'll find countless opportunities for relaxation and adventure. There's loads to experience, including its rich history and cultural experiences. Make your trip to Chester even more fun by including some sightseeing. Swarthmore College, Harrahs Casino and Racetrack and Widener University are among the big attractions you'll want to explore. Whatever your travel plans or budget, putting together a tailored Chester vacation is a cinch with Expedia.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Westampton
CA $507
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
6.6/10 (1,000 reviews)
Had misters in the hallways- affected our asthma. Only had toast, bagels, waffles and muffins for breakfast (no eggs/meat). No carpet on floors, making it slippery.
Reviewed on Oct 22, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
Comfort Inn Philadelphia International Airport West
1300 Providence Ave Chester PA
Fully refundable
CA $118
CA $131 total
Nov 15 - Nov 16
includes taxes & fees
Club Quarters Hotel Rittenhouse Square, Philadelphia
1628 Chestnut St Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $156
CA $182 total
Nov 1 - Nov 2
includes taxes & fees
Doubletree by Hilton Philadelphia Airport
4509 Island Ave Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $148
CA $172 total
Nov 23 - Nov 24
includes taxes & fees
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)
After visiting Chester City Hall, 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.
Subaru Park
7.0/10 (40 reviews)
Catch an event at Subaru Park during your trip to Chester. Amble around this family-friendly area's riverfront or attend a sporting event.
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 time in Chester? Experience the acclaimed art scene or attend a sporting event in this walkable 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
You can search for that perfect souvenir at South Chester Market Place during your stay in Chester. Visit the casinos in this family-friendly area, or simply enjoy its restaurants.
Crozier Park
Explore the great outdoors at Crozier Park, a lovely green space in Chester. Visit the casinos in this family-friendly area, or simply enjoy its restaurants.
Ethel Waters Park
Ethel Waters Park is just one of the places to see in Chester, so why not enjoy the other things to explore during your travels? Visit the casinos in this family-friendly area, or simply enjoy its restaurants.
What to do in Chester
LEGOLAND® Discovery Center Philadelphia
CA $35
per adult
80% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
CA $83
per adult
82% of travellers recommend
BYOB Historically Hilarious Trolley Tour of Philadelphia
CA $69
per adult
94% of travellers recommend
Frequently asked questions
How much does a Chester vacation package cost?
You'll find cheap prices from CA $456 on Expedia for your Chester escape. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
January, February and March are the best times to look for cheap Chester vacation packages. Choosing to travel in quieter months means you can usually find lower prices on accommodations and flights.
How many days is enough for Chester?
Chester vacations come in various shapes and sizes, but to really get a feel for this destination, we reckon 2 days is a good ballpark. With this timeframe, you can fit in major attractions like John Heinz National Wildlife Refuge at Tinicum and Morton Morton House along with hidden gems. Don't skip neighbourhoods such as Springfield and Collingdale either. If you're clever with your time, you may even be able to take a day trip outside of Chester too.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like Chester City Hall among the many things to keep you busy. Whether you're travelling with the family or planning a trip with friends, a Chester vacation promises a good time for everyone.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect 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 escape off to a flying start.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester break by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chester?
If you have your Chester vacation dates locked in, book as soon as you can to bag some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Chester?
- Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the available activities will also help you decide when to visit Chester.
- Work out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodations will likely be the largest expense during your trip to Chester.
- Decide how long to go for: Now that you're up to speed on Chester, you can work out the right length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Chester vacation 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.
