Chester Holidays

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Top hotels in Chester

Comfort Inn Philadelphia International Airport West

Comfort Inn Philadelphia International Airport West

3 out of 5
1300 Providence Ave, Chester, PA
Fully refundableReserve now, pay when you stay
The price is €82 per night from 21 Aug to 22 Aug
€82
21 Aug - 22 Aug
includes taxes & fees
7.4/10 Good! (574 reviews)
"The bus drivers were friendly and very helpful. The night agent wasn't as helpful as he could have been. I heard him give more information to another guest that could have been useful to me."

Reviewed on 15 Aug 2025

Comfort Inn Philadelphia International Airport West
Hilton Philadelphia at Penn's Landing

Hilton Philadelphia at Penn's Landing

4 out of 5
201 S. Christopher Columbus Blvd, Philadelphia, PA
Fully refundableReserve now, pay when you stay
The price is €143 per night from 31 Aug to 1 Sept
€143
31 Aug - 1 Sept
includes taxes & fees
8/10 Very Good! (1,335 reviews)
"I love the location. It’s directly on the water. You can see the bridge and the aquarium. There are also plenty of seating options and relaxation areas as well as food choices right on the other side of the driveway."

Reviewed on 17 Aug 2025

Hilton Philadelphia at Penn's Landing
Sonesta Philadelphia Rittenhouse Square

Sonesta Philadelphia Rittenhouse Square

4 out of 5
1800 Market St, Philadelphia, PA
Fully refundableReserve now, pay when you stay
The price is €118 per night from 31 Aug to 1 Sept
€118
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (1,912 reviews)
"Very beautiful place would be coming back for sure for sure 10/5 stars."

Reviewed on 17 Aug 2025

Sonesta Philadelphia Rittenhouse Square
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.

Popular places to visit

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.

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