Chester County Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top vacation destinations in Chester County

A street lined with historic buildings, a sign for Kildogge's Pub, and a banner for West Chester Restaurant Week.
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West Chester

West Chester
A pond with lily pads and purple water lilies.
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Kennett Square

Kennett Square

Top Chester County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Kimpton Hotel Monaco Philadelphia by IHG

Kimpton Hotel Monaco Philadelphia by IHG

4.5 out of 5
Center City
Price was CA $1,339, price is now CA $975 per person
CA $975
per person
Aug 28 - Aug 31
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9/10 Wonderful! (1,365 reviews)
The staff was amazing and the room was great. Clean. Would definitely recommend.

Reviewed on Jul 9, 2026

The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Center City
Price was CA $1,622, price is now CA $1,227 per person
CA $1,227
per person
Aug 28 - Aug 31
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9.6/10 Exceptional! (1,002 reviews)
Staff were friendly and helpful.

Reviewed on Jul 6, 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 $1,344, price is now CA $1,024 per person
CA $1,024
per person
Aug 28 - Aug 31
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.8/10 Excellent! (1,560 reviews)
Wonderful hotel to stay for any trip. Excellent hotel management, great stuffs, clean environment, nice rooms with nice view, great restaurants in the hotel, and absolutely a great convenient location in Philly. Highly recommended!!!!

Reviewed on Jul 5, 2026

Hotel Du Pont

Hotel Du Pont

4.5 out of 5
Downtown Wilmington
Price was CA $1,492, price is now CA $1,165 per person
CA $1,165
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
8.8/10 Excellent! (660 reviews)
First class hotel and awesome restaurant . Never disappoints. Having the Playhouse and world class Broadway dhows makes it a very special night !!

Reviewed on Jun 6, 2026

The Bellevue Hotel - The Unbound Collection by Hyatt

The Bellevue Hotel - The Unbound Collection by Hyatt

4.5 out of 5
Center City
Price was CA $1,619, price is now CA $1,268 per person
CA $1,268
per person
Aug 28 - Aug 31
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.6/10 Excellent! (1,001 reviews)
IRA is the best part of this hotel!! The WiFi was spotty but the place is beautiful and well located. The new supper club is insanely gorgeous!! And the gym!!!!!

Reviewed on Jul 2, 2026

Chester County Hotel Deals

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 $282 per night from Jul 18 to Jul 19
CA $282
CA $328 total
Jul 18 - Jul 19
includes taxes & fees
8.6/10 Excellent! (2,140 reviews)
"I loved 90% of it. Other than ( for me ) the pillows were way to soft. It took almost all the pillows just to prop my head up... and the 2nd thing was, I wish I would have had a menu in my room so I could order room service. I just wanted to relax and not be around a lot of people when trying to ..."

Reviewed on Jul 9, 2026

Philadelphia Marriott Downtown
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 $180 per night from Jul 16 to Jul 17
CA $180
CA $210 total
Jul 16 - Jul 17
includes taxes & fees
9/10 Wonderful! (4,716 reviews)
"The room was a bit small but overall we were fine. Location was nice."

Reviewed on Jul 9, 2026

Club Quarters Hotel Rittenhouse Square, Philadelphia
Sofitel Philadelphia at Rittenhouse Square

Sofitel Philadelphia at Rittenhouse Square

4.5 out of 5
120 S 17th St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Jul 27 to Jul 28
CA $227
CA $310 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (2,460 reviews)
"Amazing hotel in the Rittenhouse / Center City Area. We spent a fabulous 4 days at this hotel during the amazing 250th Independence Day celebrations. We were able to walk EVERYWHERE from going to the Art Museum for the fireworks (35 minutes) to the Old City Liberty Bell / Independence Hall (25 minutes) ..."

Reviewed on Jul 9, 2026

Sofitel Philadelphia at Rittenhouse Square
See all 4,612 properties in Chester County
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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Frequently asked questions

How much does a Chester County vacation package cost?
Get set to book, because a trip to Chester County starts from an affordable CA $975. When you bundle your hotels, flights and car rentals into a package, you'll pick up great deals.
How do I get a cheap travel package to Chester County?
You'll save loads of cash if you bundle your flights, car rentals and hotels into a Chester County vacation package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer over 550 partner airlines and 1,000,000 properties across the globe, so you'll always have plenty of options to choose from. Eager to save even more? Add some interesting activities to your package deal and unlock even bigger discounts! After all, travel is about more than just getting to your destination.
How far in advance should I book my Chester County vacation?
Reserving your flight early with Expedia means one less thing to have to worry about. Most air carriers display prices up to 12 months in advance. This is generally the cheapest time to book. If circumstances have left you booking late, low prices to Chester County occasionally appear in the weeks leading up to departure.
What does an Expedia Chester County travel package include?
With Expedia, you can select any combination of hotels, flights and car rentals to create your perfect Chester County travel package. Once you've made your booking, you can add on fun stuff like activities and tours. Don't forget, the more you bundle, the more you stand to save!
What should I know before booking a Chester County travel package?
You can save a tidy sum by combining your flights, hotels and rental cars. Once you've created your package, you can add on things like activities or tours. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Chester County Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Chester County vacation package?
You can. We understand that things don't always go to plan, so we're here to help if you have to make changes to your Chester County vacation package. It may be possible to cancel or amend your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Head to our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Stay near popular Chester County attractions

Longwood Gardens

9.2/10 (1,103 reviews)
Explore the great outdoors at Longwood Gardens, a lovely green space in Kennett Square. Stroll along the riverfront or visit the shops in this family-friendly area.
See properties

What to do in Chester County

LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

CA $35
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
The Escape Game: Epic 60-Minute Adventure at King of Prussia

The Escape Game: Epic 60-Minute Adventure at King of Prussia

CA $57
per adult
The Escape Game: Epic 60-Minute Adventure at King of Prussia
Valley Forge National Historical Park Self Driving Tour

Valley Forge Tour: Self-Guided Drive

CA $24
per traveller
Valley Forge Tour: Self-Guided Drive
See all activities in Chester County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.