Chester Vacations

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Find the Best Chester Vacation Packages

Chester Hotel Deals

Philadelphia Marriott Downtown

Philadelphia Marriott Downtown

4 out of 5
1201 Market St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is ￥32,357 per night from Jul 5 to Jul 6
￥32,357
￥37,653 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (2,099 reviews)
"Great"

Reviewed on Jul 1, 2026

Philadelphia Marriott Downtown
Sofitel Philadelphia at Rittenhouse Square

Sofitel Philadelphia at Rittenhouse Square

4.5 out of 5
120 S 17th St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is ￥26,016 per night from Jul 23 to Jul 24
￥26,016
￥35,574 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (2,429 reviews)
"Excellent location and property very clean"

Reviewed on Jul 1, 2026

Sofitel Philadelphia at Rittenhouse Square
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 ￥20,682 per night from Jul 6 to Jul 7
￥20,682
￥24,068 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,684 reviews)
"Great location We enjoyed our visit in this hotel"

Reviewed on Jul 1, 2026

Club Quarters Hotel Rittenhouse Square, Philadelphia
See all 3,203 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 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.
See properties

What to do in Chester

LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

￥3,997
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
BYOB Historically Hilarious Trolley Tour of Philadelphia

BYOB Historically Hilarious Trolley Tour of Philadelphia

￥7,758
per adult
100% of travellers recommend
BYOB Historically Hilarious Trolley Tour of Philadelphia
Dark Philly Adult Night Tour

Dark Philly Adult Night Tour

￥6,078
per adult
96% of travellers recommend
Dark Philly Adult Night Tour
See all activities in Chester

Frequently asked questions

How much does a Chester vacation 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 vacation 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 vacation packages and you could land some excellent off-season deals.
How many days is enough for Chester?
Chester vacations 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 neighborhoods 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 vacation package to Chester?
Chester offers everything you need for an unforgettable trip. Begin your Chester vacation 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 personalize 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 vacation as a package?
You can enjoy significant savings on your next Chester break by booking a personalized vacation 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 vacation 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 vacation 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.