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.
West Philadelphia Modern Hotel & Suites

West Philadelphia Modern Hotel & Suites

2 out of 5
West Philadelphia
Price was CA $1,381, price is now CA $1,140 per person
CA $1,140
per person
Jun 21 - Jun 23
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
8.6/10 Excellent! (121 reviews)
Plenty of stores around they would not give us access to the dryer just the washer, which is very irritating. They suggested you don’t use the oven but obviously we just cleaned all the oil out of the bottom of the oven so we could use them because people don’t take care of things out there, but we did so it was a good experience. However, you want to look at it.

Reviewed on Mar 14, 2026

Orchard Way

Orchard Way

2 out of 5
Price was CA $3,056, price is now CA $1,977 per person
CA $1,977
per person
Jun 21 - Jun 23
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
No reviews
Casa De Miliki

Casa De Miliki

2 out of 5
South Philadelphia
Price was CA $5,548, price is now CA $3,857 per person
CA $3,857
per person
Jun 21 - Jun 23
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
No reviews
Surrey Beach House

Surrey Beach House

2 out of 5
Price was CA $3,982, price is now CA $2,843 per person
CA $2,843
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Philadelphia (PHL)
9.8/10 Exceptional! (49 reviews)
It was adorable and modern and right near the beach. They also mailed me back the phone and watch chargers I left in the room, which was so great of them!

Reviewed on Feb 15, 2026

Tudor Lux

Tudor Lux

2 out of 5
Price was CA $6,906, price is now CA $5,284 per person
CA $5,284
per person
May 19 - May 22
just found
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
No reviews

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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 $154 per night from Apr 19 to Apr 20
CA $154
CA $179 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (4,466 reviews)
Great hotel and always love staying here. Everyone is friendly and polite. The hotel is very convenient, clean, and accessible. :)

Reviewed on Apr 12, 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 $208 per night from Apr 29 to Apr 30
CA $208
CA $242 total
Apr 29 - Apr 30
includes taxes & fees
8.6/10 Excellent! (2,724 reviews)
Nice hotel in a great location! A bit dated, and rooms could use some minor updates. Super nice to have restaurant options available connected to the hotel.

Reviewed on Apr 11, 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 $182 per night from Apr 16 to Apr 17
CA $182
CA $245 total
Apr 16 - Apr 17
includes taxes & fees
8.4/10 Very Good! (2,278 reviews)
been coming to Philly every year since 2018 and this is the only hotel I’ve stayed at. Clean, safe and staff are incredible!!!! If you’re a woman & solo traveling, I feel super safe here!

Reviewed on Apr 12, 2026

Sonesta Philadelphia Rittenhouse Square
See all 3,183 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)

Bring the kids to Sesame Place and enjoy the excitement of this 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
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
Sphinx Gallery

Penn Museum Admission Ticket

CA $31
per adult
100% of travellers recommend
Penn Museum Admission Ticket
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.