Chester Vacation Packages

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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.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Chateau Renault

Chateau Renault

4 out of 5
per person
Aug 11 - Aug 13
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
8.8/10 Excellent! (319 reviews)
Really nice rooms and very friendly staff. Especially, Jocelyn and Keaton.

Reviewed on Jun. 23, 2025

Surrey Beach House

Surrey Beach House

2 out of 5
per person
Sep 12 - Sep 15
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) 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

Anna & Bel

Anna & Bel

4 out of 5
North Philadelphia
per person
Aug 18 - Aug 21
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9.6/10 Exceptional! (37 reviews)
Exactly what I expected at the price, lovely stay, wonderful bar and restaurant.

Reviewed on Jun. 21, 2025

Home2 Suites by Hilton Philadelphia - Convention Center, PA

Home2 Suites by Hilton Philadelphia - Convention Center, PA

3 out of 5
Center City
per person
Aug 18 - Aug 21
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.2/10 Very Good! (1,008 reviews)
Clean excellent staff they went above & beyond very happy with our stay will definitely stay again

Reviewed on Jun. 26, 2025

The Maj Hotel

The Maj Hotel

3 out of 5
North Philadelphia
per person
Aug 18 - Aug 21
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9.4/10 Exceptional! (308 reviews)
Great hotel all around!

Reviewed on Jun. 30, 2025

Ready to book your vacation to Chester?

 

Choose your dates

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
The price is CA $196 per night from Jul 7 to Jul 8
CA $196
CA $260 total
Jul 7 - Jul 8
includes taxes & fees
8.2/10 Very Good! (1,753 reviews)
Great staff, questionable room, busy time
"Reception staff were all lovely, and the check-in and check-out processes were both smooth. The general state of the room left a bit to be desired: the couch/bench had several chips taken out of the base, there were weird pieces of gunk stuck to the ceiling and visible water damage on the ceiling ..."

Reviewed on Jun. 28, 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
The price is CA $138 per night from Jul 2 to Jul 3
CA $138
CA $161 total
Jul 2 - Jul 3
includes taxes & fees
8.8/10 Excellent! (1,467 reviews)
"Une bonne idée pour un cours séjour"

Reviewed on Jun. 27, 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
The price is CA $165 per night from Jul 20 to Jul 21
CA $165
CA $192 total
Jul 20 - Jul 21
includes taxes & fees
7.2/10 Good! (3,166 reviews)
"The roots festival was trash but our stay was worth it"

Reviewed on Jun. 27, 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $519 on Expedia for your Chester escape. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
January, February and March are the best times to look for cheap Chester vacation packages. Choosing to travel in quieter months means you can usually find lower prices on accommodations and flights.
How many days is enough for Chester?
Chester vacations come in various shapes and sizes, but to really get a feel for this destination, we reckon 2 days is a good ballpark. With this timeframe, you can fit in major attractions like John Heinz National Wildlife Refuge at Tinicum and Morton Morton House along with hidden gems. Don't skip neighbourhoods such as Springfield and Collingdale either. If you're clever with your time, you may even be able to take a day trip outside of Chester too.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like Chester City Hall among the many things to keep you busy. Whether you're travelling with the family or planning a trip with friends, a Chester vacation promises a good time for everyone.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Chester package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester escape off to a flying start.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester break by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chester?
If you have your Chester vacation dates locked in, book as soon as you can to bag some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Chester?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the available activities will also help you decide when to visit Chester.
  2. Work out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodations will likely be the largest expense during your trip to Chester.
  3. Decide how long to go for: Now that you're up to speed on Chester, you can work out the right length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Chester vacation package that brings all your bookings together.

Discover the most popular places to visit in Chester

Rittenhouse Square

Rittenhouse Square

4.5/5(41 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
Philadelphia Museum of Art which includes art

Philadelphia Museum of Art

4.5/5(102 reviews)

One of the country’s largest museums, with hundreds of thousands of objects, a Rodin Museum, renowned impressionist art and a sculpture garden.

Philadelphia Museum of Art
Liberty Bell Center showing a city, a monument and heritage architecture

Liberty Bell Center

4.5/5(119 reviews)

Set in the historical heart of the city, this glass pavilion that houses America’s symbol of independence is one of the most visited sights in Philadelphia.

Liberty Bell Center

What to do in Chester

Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

CA $41
per traveller
Liberty, Freedom, and Revolution: American History Tours Bundle
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions

Go City: Philadelphia All-Inclusive Pass with 30+ Attractions

CA $81
per adult
80% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
Center City Philadelphia Food Tour with Reading Market

Center City Philadelphia Food Tour with Reading Market

CA $81
per adult
Center City Philadelphia Food Tour with Reading Market
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.