Chester Vacations from $284

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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.
Doubletree by Hilton Philadelphia Airport

Doubletree by Hilton Philadelphia Airport

4 out of 5
Southwest Philadelphia
Save 100% on your flight
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
7.4/10 Good! (3,102 reviews)
Rooms were dirty, stains everywhere, even on bedding. Door handle to the bathroom was broken. Don’t let the lobby’s looks fool you!

Reviewed on Jun 20, 2025

Hilton Garden Inn Philadelphia Center City

Hilton Garden Inn Philadelphia Center City

3 out of 5
Center City
Save 100% on your flight
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
8.6/10 Excellent! (1,592 reviews)
Being right next to reading terminal market makes it the best location ever. Outlets didn’t work for one of the beds so that was annoying.

Reviewed on Jun 20, 2025

Valley Forge Casino Resort

Valley Forge Casino Resort

4 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
8.2/10 Very Good! (1,003 reviews)
Comfortable and quiet room. Pleasant stay and fun in Casino.

Reviewed on Jun 20, 2025

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
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
8.6/10 Excellent! (1,000 reviews)
Great staff and experience

Reviewed on Jun 19, 2025

Sonesta Philadelphia Rittenhouse Square

Sonesta Philadelphia Rittenhouse Square

4 out of 5
Center City
Save 100% on your flight
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
8.4/10 Very Good! (1,712 reviews)
The room was okay. But the pillows were dirty. I have pictures, 3 of the pillows were stained prior to us sleeping.

Reviewed on Jun 19, 2025

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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
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

$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

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
$127 nightly
The price is $147 total per night from Jul 6 to Jul 7
$147 total
Jul 6 - Jul 7
Total includes taxes and fees
8.4/10 Very Good! (1,592 reviews)
"This facility was very clean, updated, and had very friendly and helpful staff!"

Reviewed on Jun 19, 2025

Hilton Garden Inn Philadelphia Center City
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
$122 nightly
The price is $141 total per night from Jul 20 to Jul 21
$141 total
Jul 20 - Jul 21
Total includes taxes and fees
8.6/10 Excellent! (4,023 reviews)
"Good coffee, very friendly front desk, good location"

Reviewed on Jun 18, 2025

Club Quarters Hotel Rittenhouse Square, Philadelphia
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
$143 nightly
The price is $167 total per night from Jul 20 to Jul 21
$167 total
Jul 20 - Jul 21
Total includes taxes and fees
8.4/10 Very Good! (1,394 reviews)
"Sheraton Suites exceeded my expectations. The check in process was quick and the person at the front desk was friendly and made sure that we were comfortable. The room was spacious and clean. The shuttle to the airport ran every 20 minutes, on time."

Reviewed on Jun 17, 2025

Sheraton Suites Philadelphia Airport
See all 2,949 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 $284 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.