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.
Valley Forge Casino Resort

Valley Forge Casino Resort

4 out of 5
Save 100% on your flight
per person
Sep 11 - Sep 16
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Philadelphia (PHL)
8.2/10 Very Good! (1,010 reviews)
Everything you need is in the hotel. Plus close to the mall and topgolf is literally across the street!

Reviewed on Jul. 6, 2025

Sheraton Philadelphia Downtown

Sheraton Philadelphia Downtown

4 out of 5
Center City
Save 100% on your flight
per person
Sep 11 - Sep 16
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Philadelphia (PHL)
8.2/10 Very Good! (1,019 reviews)
It was clean and staff was friendly.

Reviewed on Jun. 27, 2025

Hyatt Centric Center City Philadelphia

Hyatt Centric Center City Philadelphia

4 out of 5
Center City
Save 100% on your flight
per person
Sep 11 - Sep 16
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Philadelphia (PHL)
9.4/10 Exceptional! (1,380 reviews)
The beds and pillows are the softest I’ve ever laid in . The location is perfect . You can walk and feel safe . The staff is very nice and attentive.

Reviewed on Jul. 10, 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
Sep 11 - Sep 16
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Philadelphia (PHL)
8.6/10 Excellent! (1,000 reviews)
Liked the fact that I was able to check in a little earlier. The only thing that I didn’t like was the shades in the room. I felt closed in as closing shades made it very dark and gloomy. Something more welcoming that allows you to see out / while light shines in / while still feeling secure and having privacy is more inviting! Thank you; I was satisfied with the friendly staff on July 5 and just overall thru July 7.

Reviewed on Jul. 7, 2025

The Warwick Hotel Rittenhouse Square Philadelphia

The Warwick Hotel Rittenhouse Square Philadelphia

4 out of 5
Center City
Save 100% on your flight
per person
Sep 11 - Sep 16
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Philadelphia (PHL)
7.8/10 Good! (1,569 reviews)
Great location. Rooms are outdated for the cost. Old wall AC units which are very noisy. Lots of wear and tear. Lobby is updated. Rooms are apparently in process or at least planned.

Reviewed on Jun. 22, 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 $174 per night from Jul 20 to Jul 21
CA $174
CA $234 total
Jul 20 - Jul 21
includes taxes & fees
8.2/10 Very Good! (1,783 reviews)
"The rooms were clean. Excellent location close to everything. The staff was amazing to me and my kids. Very patient and attentive. Loved that there was an outside pool as well. First time here and now is my favorite place to stay in Center City."

Reviewed on Jul. 8, 2025

Sonesta Philadelphia Rittenhouse Square
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 CA $128 per night from Jul 20 to Jul 21
CA $128
CA $149 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (4,032 reviews)
We lucked out. Great corner room.
"We got a corner room on the 11th floor with a super high ceiling. It was difficult to get around the bed but the high ceilings and the corner room (both views looked out onto the city) was such a bonus!!!! Thank you Club Quarters! And free nespresso in the room! And in the lobby, free flat and sparkling ..."

Reviewed on Jul. 8, 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 CA $164 per night from Jul 20 to Jul 21
CA $164
CA $191 total
Jul 20 - Jul 21
includes taxes & fees
7.2/10 Good! (3,237 reviews)
"Property was ok, bed was very very soft, bathtub was stained black and was not very clean. Encased window was peeling and cracking. Positive side- Staff as awesome and amazing and very helpful."

Reviewed on Jul. 8, 2025

Doubletree by Hilton Philadelphia Airport
See all 3,009 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

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 fascinating museums and acclaimed theater scene 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

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $589 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.

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