Chester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Philadelphia (PHL)
8.2/10 Very Good! (1,006 reviews)
The customer service is by far the best we have EVER received at any stay at any hotel the we have been too!!!! The staff is amazing and super friendly!! Always had smiles on their faces:) We would definitely book here again!!!

Reviewed on Aug. 3, 2025

The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Center City
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Philadelphia (PHL)
9.6/10 Exceptional! (864 reviews)
We celebrated our 21st wedding anniversary at the Rittenhouse and they made it extremely special for us. We felt like royalty staying there in a really spacious room overlooking the park. I enjoyed the soaking tub. It was spacious enough that we felt we could live there. The staff was amazing and went above and beyond to help make our anniversary feel special, which we deeply appreciated. This hotel offers a nice indoor pool as well as fitness center, which we got to use, but if we had had more days we would have used more. I did enjoy a Rolfing massage before leaving this hotel, which was a new experience for me and a great relief. My Massage Therapist 💆‍♀️ was extremely skilled and successful at relieving my pain. The only thing that would keep us from returning to the Rittenhouse is the pungent odors from the park where a lot of people smoke weed openly and other smells coming from the vents underground.

Reviewed on Aug. 2, 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
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Philadelphia (PHL)
8.8/10 Excellent! (1,001 reviews)
Very clean, staff members were all very nice, valet parking was easy to use and complimentary breakfast!

Reviewed on Aug. 8, 2025

Renaissance Philadelphia Downtown Hotel

Renaissance Philadelphia Downtown Hotel

4 out of 5
Center City
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Philadelphia (PHL)
8.4/10 Very Good! (1,003 reviews)
This is a great location that’s convenient to museums and the Liberty Bell and Independence Hall and the hop on hop off bus pickup locations. The staff is professional and courteous. We will be back!

Reviewed on Aug. 4, 2025

The Warwick Hotel Rittenhouse Square Philadelphia

The Warwick Hotel Rittenhouse Square Philadelphia

4 out of 5
Center City
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Philadelphia (PHL)
7.8/10 Good! (1,527 reviews)
Rooms were pretty dated, shower in not great condition. Staff super nice and helpful.

Reviewed on Jul. 20, 2025

Ready to book your vacation to Chester?

 

Choose your dates

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 CA $131 per night from Sep 7 to Sep 8
CA $131
CA $143 total
Sep 7 - Sep 8
includes taxes & fees
7.4/10 Good! (563 reviews)
"Decent"

Reviewed on Aug. 8, 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 CA $126 per night from Aug 17 to Aug 18
CA $126
CA $146 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (4,023 reviews)
"Definitely one of the best hotels I’ve stayed at. All around convenient and cleanliness!"

Reviewed on Aug. 6, 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 $150 per night from Aug 17 to Aug 18
CA $150
CA $175 total
Aug 17 - Aug 18
includes taxes & fees
7.2/10 Good! (3,427 reviews)
Great Personalities
"The staff was friendly especially Jermaine and Tyrah at the front desk! It was clean and inviting! Everyone had a smile and greeted me with kindness!"

Reviewed on Aug. 8, 2025

Doubletree by Hilton Philadelphia Airport
See all 2,899 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
Polaris Slingshot Rental-Philadelphia, PA

Polaris Slingshot Rental-Philadelphia, PA

CA $343
per traveller
Polaris Slingshot Rental-Philadelphia, PA
See all activities in Chester

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $694 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.