Chester Vacations from ￥280,439

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The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Towneplace Suites Cranbury South Brunswick

Towneplace Suites Cranbury South Brunswick

3 out of 5
per person
Aug 11 - Aug 17
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Trenton (TTN)
9.2/10 Wonderful! (456 reviews)
Solid stay. Rooms were spacious and clean. Hotel staff was very accommodating as well!

Reviewed on Jun 11, 2025

Find the Best Chester Vacation Packages

Chester Hotel Deals

Sheraton Suites Philadelphia Airport
Sheraton Suites Philadelphia Airport
3.5 out of 5
4101b Island Ave, Philadelphia, PA
Fully refundableReserve now, pay when you stay
The price is ￥20,618 per night from Jul 13 to Jul 14
￥20,618
￥23,994 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very Good! (1,409 reviews)
"Great room. Very nice, helpful staff. Convenient to airport and Philly."

Reviewed on Jun 24, 2025

Sheraton Suites Philadelphia Airport
Hilton Garden Inn Philadelphia Center City
Hilton Garden Inn Philadelphia Center City
3 out of 5
1100 Arch St, Philadelphia, PA
Fully refundableReserve now, pay when you stay
The price is ￥18,390 per night from Jul 6 to Jul 7
￥18,390
￥21,400 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very Good! (1,626 reviews)
"The staff was friendly and accommodating"

Reviewed on Jun 25, 2025

Hilton Garden Inn Philadelphia Center City
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 ￥17,521 per night from Jul 20 to Jul 21
￥17,521
￥20,390 total
Jul 20 - Jul 21
includes taxes & fees
7.2/10 Good! (3,148 reviews)
"Nice hotel, convenient to airport. Needs some sprucing up, carpet on our floor was all torn and frayed. Not particularly attractive as we made our way to our room"

Reviewed on Jun 24, 2025

Doubletree by Hilton Philadelphia Airport
See all 2,996 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.

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from ￥280,439 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.

Discover the most popular places to visit in Chester

Rittenhouse Square which includes street scenes and a park

Rittenhouse Square

4.5/5(1,315 reviews)

Rittenhouse Square is just one of the places to see in Philadelphia, so why not enjoy the other things to explore during your travels? Experience the acclaimed art scene and entertainment choices in this vibrant area.

Rittenhouse Square
A church that is part of the U Penn landscape

University of Pennsylvania

4.5/5(948 reviews)

Walk around the campus of University of Pennsylvania, a top college in Philadelphia. Experience the acclaimed art scene and fascinating museums in this vibrant area.

University of Pennsylvania
Pennsylvania Convention Center

Pennsylvania Convention Center

4.5/5(875 reviews)

During your trip, find out what's happening at Pennsylvania Convention Center, a top convention center in Philadelphia. Experience the great live music or attend a sporting event in this vibrant area.

Pennsylvania Convention Center

What to do in Chester

Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

￥3,686
per traveler
Liberty, Freedom, and Revolution: American History Tours Bundle
Center City Philadelphia Food Tour with Reading Market

Center City Philadelphia Food Tour with Reading Market

￥8,531
per adult
Center City Philadelphia Food Tour with Reading Market
Polaris Slingshot Rental-Philadelphia, PA

Polaris Slingshot Rental-Philadelphia, PA

￥36,150
per traveler
Polaris Slingshot Rental-Philadelphia, PA
See all activities in Chester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.