Chester Vacations from ￥158,392

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The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area

2 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Philadelphia (PHL)
6.6/10 (936 reviews)
Kumar, the manager allowed me and my family to be on adjacent rooms even though we booked seperately. That made a huge difference with our stay. Plus the hotel is near everything. Thank you!

Reviewed on Aug 9, 2025

Find the Best Chester Vacation Packages

Chester Hotel Deals

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 ￥13,693 per night from Aug 17 to Aug 18
￥13,693
￥14,925 total
Aug 17 - Aug 18
includes taxes & fees
7.4/10 Good! (568 reviews)
"We get offer free breakfast, staff gave us information good food places in Philadelphia, and there we available catalogs and maps in the lobby."

Reviewed on Aug 10, 2025

Comfort Inn Philadelphia International Airport West
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 ￥13,967 per night from Aug 31 to Sep 1
￥13,967
￥16,253 total
Aug 31 - Sep 1
includes taxes & fees
8.8/10 Excellent! (4,049 reviews)
"I booked by mistake for the 25.08 25 to 26.08.25 Itinerary # 73204530703699 please could arrange the refund View full itinerary Traveller details Adults, 2 Club Quarters Hotel Rittenhouse Square, Philadelphia   1628"

Reviewed on Aug 12, 2025

Club Quarters Hotel Rittenhouse Square, Philadelphia
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 ￥17,461 per night from Aug 31 to Sep 1
￥17,461
￥20,318 total
Aug 31 - Sep 1
includes taxes & fees
7.2/10 Good! (3,454 reviews)
"Excellent"

Reviewed on Aug 11, 2025

Doubletree by Hilton Philadelphia Airport
See all 2,918 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.

Discover the most popular places to visit in Chester

Rittenhouse Square which includes street scenes and a park

Rittenhouse Square

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 fascinating museums and acclaimed theater scene in this vibrant area.

Rittenhouse Square
Pennsylvania Convention Center

Pennsylvania Convention Center

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

Pennsylvania Convention Center
If you can, get club box seats at the Flyers game for a great view and intimate bar and private restrooms, away from the crowds.

Wells Fargo Center

Catch an event at Wells Fargo Center during your trip to Philadelphia. Experience the fascinating museums and great live music in this vibrant area.

Wells Fargo Center

What to do in Chester

Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

￥4,429
per traveler
Liberty, Freedom, and Revolution: American History Tours Bundle
Polaris Slingshot Rental-Philadelphia, PA

Polaris Slingshot Rental-Philadelphia, PA

￥36,923
per traveler
Polaris Slingshot Rental-Philadelphia, PA
Center City Philadelphia Food Tour with Reading Market

Center City Philadelphia Food Tour with Reading Market

￥8,714
per adult
80% of travellers recommend
Center City Philadelphia Food Tour with Reading Market
See all activities in Chester

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from ￥158,392 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.

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