Chester County Vacation Packages
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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.
Cozy Home near City Center with Hot tub
South Philadelphia
CA $4,138
per person
Oct 2 - Oct 5
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) 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
Hyatt Centric Rittenhouse Square Philadelphia
Center City
CA $1,307
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Philadelphia (PHL)
9.4/10 Exceptional! (1,730 reviews)
Awesome hotel! Clean, updated room. Staff was exceptional with all of our requests. Would stay here again!
Reviewed on Aug 23, 2026
Chester County Hotel Deals
Loews Philadelphia Hotel
1200 Market St Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $248
CA $288 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (1,993 reviews)
"Great hotel. All staff members were extremely friendly and helpful."
Reviewed on Aug 25, 2026
Motto by Hilton Philadelphia Rittenhouse Square
31 S 19th St Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $135
CA $157 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (2,416 reviews)
"Nice hotel, nice staff, the restaurants and bar amazing. The room is okay some accessories were broken in the bathroom but in general it was good. I would've appreciate coffee in the room"
Reviewed on Aug 25, 2026
W Philadelphia
1439 CHESTNUT ST Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $293
CA $341 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (1,314 reviews)
"I absolutely adore the W hotel. The aesthetics is on point. Love the pool. I wish they would bring back the $20 Sunday funday that they had back during the pandemic times. The only thing that sucked was a fire alarm went off at like 5/6am . When you’re drunk as a skunk tryna get some shut eye in, ..."
Reviewed on Aug 25, 2026
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 $1,018. 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.
