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.
One Sky Loft

One Sky Loft

2 out of 5
Center City
Price was CA $3,754, price is now CA $2,593 per person
CA $2,593
per person
Jun 21 - Jun 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
9.4/10 Exceptional! (76 reviews)
We loved our stay. Clean, comfortable, quiet. Excellent location. Safe area. Absolutely fantastic and we will be back.

Reviewed on Apr 8, 2026

Cozy Home near City Center with Hot tub

Cozy Home near City Center with Hot tub

3 out of 5
South Philadelphia
Price was CA $12,228, price is now CA $6,208 per person
CA $6,208
per person
Jun 18 - Jun 21
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
10/10 Exceptional! (3 reviews)
This was the perfect place for my group and our needs. Enough beds with options; a dark, quiet room in the basement, a shared room with a two full beds, the top floor king size suite, even a pull out sofa! All useful accommodations for a party of 5 or more. To top it off, the roof top hot tub with a city skyline view was incredible! It was a great location too, in walking distance to our venue in South Philly. Everything worked out perfectly, and I'm grateful that this option was available. Thank you!

Reviewed on Mar 2, 2026

Orchard Way

Orchard Way

2 out of 5
Price was CA $4,152, price is now CA $2,631 per person
CA $2,631
per person
Jun 18 - Jun 21
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
No reviews
Casa De Miliki

Casa De Miliki

2 out of 5
South Philadelphia
Price was CA $7,861, price is now CA $5,475 per person
CA $5,475
per person
Jun 18 - Jun 21
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
No reviews
The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Center City
Price was CA $3,782, price is now CA $2,739 per person
CA $2,739
per person
Jun 21 - Jun 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
9.6/10 Exceptional! (981 reviews)
Great hotel in rittenhouse square.

Reviewed on Apr 1, 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 $153 per night from Apr 26 to Apr 27
CA $153
CA $178 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,462 reviews)
Perfect hotel! Highly Recommend!

Reviewed on Apr 16, 2026

Club Quarters Hotel Rittenhouse Square, Philadelphia
The Windsor Suites

The Windsor Suites

4 out of 5
1700 Ben Franklin Pkwy Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Apr 29 to Apr 30
CA $207
CA $240 total
Apr 29 - Apr 30
includes taxes & fees
8.6/10 Excellent! (2,721 reviews)
One of my favorite places to stay. So convenient and clean and very staff friendly. They cater to you and your needs and are quick to take care of you.

Reviewed on Apr 16, 2026

The Windsor Suites
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 $195 per night from Apr 26 to Apr 27
CA $195
CA $259 total
Apr 26 - Apr 27
includes taxes & fees
8.4/10 Very Good! (2,267 reviews)
Our room was huge and the beds so comfortable. Everything was spotless. The only breakfast option was the coffee shop which wasn't very exciting, best to find a local diner.

Reviewed on Apr 13, 2026

Sonesta Philadelphia Rittenhouse Square
See all 3,192 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.
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Discover the most popular places to visit in Chester

Aerial of Theme Park

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.

Sesame Place
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 theater scene and great live music in this vibrant area.

Rittenhouse Square
Philadelphia Museum of Art

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.

Philadelphia Museum of Art

What to do in Chester

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
LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

CA $34
per adult
LEGOLAND® Discovery Center Philadelphia
Go City: Philadelphia Explorer Pass - Choose 3 to 7 Attractions

Go City: Philadelphia Explorer Pass - Choose 3 to 7 Attractions

CA $81
per adult
76% of travellers recommend
Go City: Philadelphia Explorer Pass - Choose 3 to 7 Attractions
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.