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.
Kimpton Hotel Monaco Philadelphia by IHG
Center City
Price was CA $1,311, price is now CA $1,074 per person
CA $1,074
per person
Aug 22 - Aug 26
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9/10 Wonderful! (1,330 reviews)
We particularly liked the breakfast every morning and the happy hour from 5-6. The staff was extremely responsive. We would definitely stay here again particularly for the proximity to the Philly sites. The Visitor's Center, Independence Hall and Liberty Bell are within a block or two. Thanks for a great stay.
Reviewed on May 28, 2026
The Logan Philadelphia, Curio Collection by Hilton
Center City
Price was CA $1,538, price is now CA $1,132 per person
CA $1,132
per person
Aug 22 - Aug 26
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.8/10 Excellent! (1,535 reviews)
Lobby bar is a scene. The drinks are decent. The pool room is fun. The Urban Room bartenders make good drinks, but the food / menu is a bit overrated and overpriced. Rooms are standard no complaints.
Reviewed on May 28, 2026
Valley Forge Casino Resort
Price was CA $1,473, price is now CA $1,151 per person
CA $1,151
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Philadelphia (PHL)
8.4/10 Very Good! (1,134 reviews)
The casino was fun and the service desk was nice. They didn't have promotions for new members. We did valet parking which was affordable. The beds are a little too firm for my liking but the AC was nice and cold. I didn't get breakfast because it wasn't made to order and a little pricey. That's expected for a casino restaurant. I was able to order Uber eats and the wait wasn't long. Plus the driver was easy to find. Overall, it was worth the stay and a nice get away. Also, it's not too far from the mall and a great location.
Reviewed on May 27, 2026
Kimpton Hotel Palomar Philadelphia by IHG
Center City
Price was CA $1,315, price is now CA $1,079 per person
CA $1,079
per person
Aug 22 - Aug 26
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9/10 Wonderful! (1,155 reviews)
Great location and staff.
Room/Carpet & bed could use an update.
Happy Hour was great
Reviewed on May 26, 2026
Loews Philadelphia Hotel
Center City
Price was CA $1,402, price is now CA $1,163 per person
CA $1,163
per person
Aug 22 - Aug 26
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9.2/10 Wonderful! (1,825 reviews)
One of my favorite hotels in Philadelphia
Reviewed on May 29, 2026
Chester Hotel Deals
Club Quarters Hotel Rittenhouse Square, Philadelphia
1628 Chestnut St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Jun 7 to Jun 8
CA $164
CA $191 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (4,589 reviews)
"Nice compact hotel but no amenities like breakfast at minimum. Rained my entire stay so bummer I had to leave hotel to get food"
Reviewed on May 29, 2026
Philadelphia Marriott Downtown
1201 Market St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $259 per night from Jun 12 to Jun 13
CA $259
CA $302 total
Jun 12 - Jun 13
includes taxes & fees
8.6/10 Excellent! (2,009 reviews)
"Hotel was amazing. Only downfall is that the $250 hold they added to my account for incidentals. That was too high in my opinion considering I had to wait 3-5 days to get it back after I checked out."
Reviewed on May 29, 2026
Sheraton Suites Philadelphia Airport
4101b Island Ave Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Jun 7 to Jun 8
CA $233
CA $271 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (2,150 reviews)
"The building is nice looking from both the outside and inside with plenty of parking. Parking is quite expensive at $25/night"
Reviewed on May 29, 2026
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.
Discover the most popular places to visit in Chester
Sesame Place
4/5(13 reviews)
Enjoy the rides and games at Sesame Place and find out why this is a popular theme park in Oxford Valley. Attend a sporting event in this family-friendly area.
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.
Philadelphia Museum of Art
4.5/5(104 reviews)
One of the country’s largest museums, with hundreds of thousands of objects, a Rodin Museum, renowned impressionist art and a sculpture garden.
What to do in Chester
Center City Philadelphia Food Tour with Reading Market
CA $81
per adult
88% of travellers recommend
BYOB Historically Hilarious Trolley Tour of Philadelphia
CA $66
per adult
100% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
CA $34
per adult
80% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
