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.
Holiday Inn Express Bordentown - Trenton South by IHG

Holiday Inn Express Bordentown - Trenton South by IHG

2.5 out of 5
Price was CA $962, price is now CA $764 per person
CA $764
per person
Jul 12 - Jul 17
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
8.4/10 Very Good! (1,009 reviews)
Staff was helpful and attentive. Wi-Fi in the hotel is very poor.

Reviewed on May 28, 2026

The Logan Philadelphia, Curio Collection by Hilton

The Logan Philadelphia, Curio Collection by Hilton

4.5 out of 5
Center City
Price was CA $1,313, price is now CA $1,001 per person
CA $1,001
per person
Aug 14 - Aug 17
found 10 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

Valley Forge Casino Resort

4 out of 5
Price was CA $1,119, price is now CA $872 per person
CA $872
per person
Aug 14 - Aug 17
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.4/10 Very Good! (1,145 reviews)
Request Room Service after second day stay, no service was provided, had to go to reception and get fresh towels and reminded them that room service was not performed.

Reviewed on Jun 2, 2026

Surrey Beach House

Surrey Beach House

2 out of 5
Price was CA $2,138, price is now CA $1,685 per person
CA $1,685
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9.8/10 Exceptional! (51 reviews)
Perfect place to stay for a beach vacation . Clean rooms and great location . Would stay there again !

Reviewed on May 29, 2026

The Windsor Suites

The Windsor Suites

4 out of 5
Center City
Price was CA $1,220, price is now CA $963 per person
CA $963
per person
Aug 14 - Aug 17
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.6/10 Excellent! (2,864 reviews)
Parking was very taxing. The staff parking were not pleasant and not helpful. Shower temperature was hard to adjust water temperature. Hard to get new towels. Needing to wait. The towels didn’t look clean and fresh. Front desk staff was awesome and most helpful!

Reviewed on Jun 2, 2026

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Chester Hotel Deals

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 $176 per night from Jun 7 to Jun 8
CA $176
CA $205 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (4,611 reviews)
"Nice"

Reviewed on Jun 1, 2026

Club Quarters Hotel Rittenhouse Square, Philadelphia
Philadelphia Marriott Downtown

Philadelphia Marriott Downtown

4 out of 5
1201 Market St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from Jun 7 to Jun 8
CA $289
CA $337 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (2,011 reviews)
"Great central location. Staff was excellent in answering questions about amenities. The room was also clean and quiet. Looking forward to staying again next time I visit Philadelphia"

Reviewed on Jun 1, 2026

Philadelphia Marriott Downtown
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
The price is CA $234 per night from Jun 7 to Jun 8
CA $234
CA $272 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (2,162 reviews)
"Great service at the front desk"

Reviewed on Jun 1, 2026

Sheraton Suites Philadelphia Airport
See all 3,201 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

Aerial of Theme Park

Sesame Place

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.

Sesame Place
Rittenhouse Square

Rittenhouse Square

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

Philadelphia Museum of Art

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

What to do in Chester

Center City Philadelphia Food Tour with Reading Market

Center City Philadelphia Food Tour with Reading Market

CA $81
per adult
88% of travellers recommend
Center City Philadelphia Food Tour with Reading Market
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions

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

CA $81
per adult
82% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
BYOB Historically Hilarious Trolley Tour of Philadelphia

BYOB Historically Hilarious Trolley Tour of Philadelphia

CA $66
per adult
100% of travellers recommend
BYOB Historically Hilarious Trolley Tour of Philadelphia
See all activities in Chester

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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.