Chester County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Jeff White
  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top vacation destinations in Chester County

A pond with lily pads and purple water lilies.

Kennett Square

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

West Chester

West Chester

Top Chester County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Chic & Cozy Philly Stay in City Center

Chic & Cozy Philly Stay in City Center

South Philadelphia
CA $1,149
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Philadelphia (PHL)
8.4/10 Very good! (7 reviews)
Little trouble getting in but host was responsive despite the late hour. I would have appreciated a more accurate description of the parking situation. Not only is there no parking on site, there is no parking anywhere close. The place is nice and roomy.

Reviewed on Aug 2, 2026

Orchard Way

Orchard Way

CA $1,803
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
No reviews
Surrey Beach House

Surrey Beach House

CA $1,312
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Philadelphia (PHL)
9.6/10 Exceptional! (58 reviews)
You have to know that you’re getting into a situation that is unlike most. There is no actual person on site and everything is done by Texting on the other hand. They are super responsive and handle every question we had quickly and appropriately. Personally, I wouldn’t want to stay more than two nights because there is no room refreshing and I’m glad that we only brought one car because that is among the greatest challenges. We were lucky and we found a space on the street that was free, but we were afraid to move it so we simply used Ubers everywhere we needed to go.

Reviewed on Aug 21, 2026

New Season Royals

New Season Royals

CA $1,552
per person
Oct 10 - Oct 15
found 23 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philadelphia (PHL)
9.2/10 Wonderful! (150 reviews)
AKA University City

AKA University City

West Philadelphia
CA $1,316
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
9.2/10 Wonderful! (840 reviews)

Chester County Hotel Deals

Loews Philadelphia Hotel

Loews Philadelphia Hotel

1200 Market St Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $246
CA $287 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (1,991 reviews)
"Great staff on site. Check in, check out, lounge, room cleanliness all excellent."

Reviewed on Aug 23, 2026

Loews Philadelphia Hotel
Motto by Hilton Philadelphia Rittenhouse Square

Motto by Hilton Philadelphia Rittenhouse Square

31 S 19th St Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $123
CA $143 total
Aug 30 - Aug 31
includes taxes & fees
Motto by Hilton Philadelphia Rittenhouse Square
W Philadelphia

W Philadelphia

1439 CHESTNUT ST Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $291
CA $339 total
Aug 31 - Sep 1
includes taxes & fees
W Philadelphia
See all 4,516 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.

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 $1,149. 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

A pond with lily pads and water lilies.
Photo by Jeff White

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
Shelves stocked with various bottles of alcohol, including wine and spirits, with some bottles having red bows.
Photo by Michael Kercsmar

Chaddsford Winery

9.0/10 (13 reviews)
You can enjoy a tasting or tour at Chaddsford Winery during your travels to Chadds Ford. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

QVC Studio Park

7.4/10 (24 reviews)
Enjoy an outing to QVC Studio Park during your stay in West Chester. Discover the area's fascinating museums and shops.
See properties

Pennhurst Asylum Haunted House

10.0/10 (1 review)
You can spend an afternoon browsing the exhibits at Pennhurst Asylum Haunted House during your travels in Spring City. Discover the area's desert landscape and cathedral.
See properties

Exton Square Mall

7.4/10 (150 reviews)
You can find the perfect gifts to bring home at Exton Square Mall during your trip to Exton. While you're in the area, wander around picturesque gardens.
See properties

Dowington Country Club

6.6/10 (4 reviews)
Enjoy a round of golf in Downingtown at Dowington Country Club. While you're in the area, wander around the forests.
See properties

What to do in Chester County

LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

CA $39
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
Valley Forge National Historical Park Self Driving Tour

Valley Forge Tour: Self-Guided Drive

CA $24
per traveller
Valley Forge Tour: Self-Guided Drive
Playground

The Escape Game: 60-Minute Adventures at King of Prussia Mall

CA $61
per adult
The Escape Game: 60-Minute Adventures at King of Prussia Mall
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.