Chester Vacations from $309

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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.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

2.5 out of 5
Center City
Save 100% on your flight
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
8.6/10 Excellent! (1,000 reviews)
This property was centrally located. We were impressed with the quality of the complimentary breakfast. Our room had hard floors (no carpet) which I appreciate!

Reviewed on Jun 25, 2025

Canopy by Hilton Philadelphia Center City

Canopy by Hilton Philadelphia Center City

4 out of 5
Center City
Save 100% on your flight
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
9.2/10 Wonderful! (1,718 reviews)
Loved the location, amenities, cleanliness.

Reviewed on Jun 27, 2025

Surrey Beach House

Surrey Beach House

2 out of 5
Save 100% on your flight
per person
Aug 13 - Aug 20
found 23 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Philadelphia (PHL)
9.8/10 Exceptional! (37 reviews)
The property was perfect for a beach weekend! Right on the beach block, clean, plenty of amenities, etc. Check in and check out was easy.

Reviewed on May 25, 2025

Sonesta Philadelphia Rittenhouse Square

Sonesta Philadelphia Rittenhouse Square

4 out of 5
Center City
Save 100% on your flight
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
8.4/10 Very Good! (1,744 reviews)
The hotel is the center of the town and easy access to the city.

Reviewed on Jul 2, 2025

Philadelphia Marriott Old City

Philadelphia Marriott Old City

4 out of 5
Center City
Save 100% on your flight
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
8.4/10 Very Good! (1,007 reviews)
The room was beautiful. However, shower leaked (enough to bother during the night), room phone did not work and air conditioner was very loud and difficult to keep stabilized temperature wise. Otherwise, the hotel is amazing! The room service was fast and the food delicious!!

Reviewed on Jul 2, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chester
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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)

Relax on grassy lawns, browse interesting sculptures and attend vibrant festivals at this historic square and popular city gathering point.

Rittenhouse Square
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
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

4.5/5(824 reviews)

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

$25
per traveler
Liberty, Freedom, and Revolution: American History Tours Bundle
Polaris Slingshot Rental-Philadelphia, PA

Polaris Slingshot Rental-Philadelphia, PA

$250
per traveler
Polaris Slingshot Rental-Philadelphia, PA
Philadelphia: The Franklin Institute Entry Ticket

Philadelphia: The Franklin Institute Entry Ticket

$29
per adult
Philadelphia: The Franklin Institute Entry Ticket
See all activities in Chester

Chester Hotel Deals

Sonesta Philadelphia Rittenhouse Square
Sonesta Philadelphia Rittenhouse Square
4 out of 5
1800 Market St, Philadelphia, PA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $162 total per night from Jul 10 to Jul 11
$162 total
Jul 10 - Jul 11
Total includes taxes and fees
8.2/10 Very Good! (1,759 reviews)
"The hotel is the center of the town and easy access to the city."

Reviewed on Jul 2, 2025

Sonesta Philadelphia Rittenhouse Square
Motto by Hilton Philadelphia Rittenhouse Square
Motto by Hilton Philadelphia Rittenhouse Square
3.5 out of 5
31 S 19th St, Philadelphia, PA
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $117 total per night from Aug 3 to Aug 4
$117 total
Aug 3 - Aug 4
Total includes taxes and fees
8.8/10 Excellent! (1,463 reviews)
"Great experience."

Reviewed on Jun 30, 2025

Motto by Hilton Philadelphia Rittenhouse Square
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
$123 nightly
The price is $143 total per night from Jul 27 to Jul 28
$143 total
Jul 27 - Jul 28
Total includes taxes and fees
7.2/10 Good! (3,203 reviews)
"Great place! I totally recommend"

Reviewed on Jul 2, 2025

Doubletree by Hilton Philadelphia Airport
See all 3,014 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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Philadelphia Intl. Airport (PHL)
Population
34,100
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Philadelphia Museum of Art, Philadelphia Zoo and Mann Center for the Performing Arts

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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from $309 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?
November, December and January are great times to look for cheap Chester vacation packages. Choosing to travel in quieter periods means you can generally find lower prices on flights and hotels.
How many days is enough for Chester?
Chester vacations come in various shapes and sizes, but to really sink your teeth into this place, we reckon 2 days is a good ballpark. In this timeframe, you can fit in top attractions like Chester City Hall and Widener University and track down some lesser-known spots. Don't forget to visit cool neighborhoods such as Springfield and Upland either. If you're smart with your time, you may even be able to take a day trip from Chester too.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like Subaru Park among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Chester vacation promises a good time for everyone.
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.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Jet off on your dream escape to Chester with our Book Now, Pay Later vacations. No need to save like crazy or hold off until the next payday --- we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.