Chester County Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top vacation destinations in Chester County
Kennett Square
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
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
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
Chester County Hotel Deals
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
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
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
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
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.
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.
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.
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.
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.
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.
What to do in Chester County
LEGOLAND® Discovery Center Philadelphia
CA $39
per adult
80% of travellers recommend
The Escape Game: 60-Minute Adventures at King of Prussia Mall
CA $61
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
