Chester County Vacation Packages
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Top vacation destinations in Chester County
West Chester
Kennett Square
Top Chester County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Windsor Suites
Center City
CA $1,217
per person
Dec 23 - Dec 27
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.8/10 Excellent! (3,295 reviews)
I had a really good time at this hotel. It was clean. Staff was friendly. The floors were amazing. The walls were amazing. The bathroom was nice like I can’t keep Raving about it!!! I will definitely be going back.
Reviewed on Oct 8, 2026
Chic & Cozy Philly Stay in City Center
South Philadelphia
CA $1,693
per person
Nov 19 - Nov 22
found 15 hours ago
Roundtrip flight included
Montreal (YMQ) 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
Chester County Hotel Deals
Club Quarters Hotel Rittenhouse Square, Philadelphia
1628 Chestnut St Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $198
CA $230 total
Oct 13 - Oct 14
includes taxes & fees
9/10 Wonderful! (4,836 reviews)
"Great area, coffee and water bar was a nice perk. Room was very clean. Bathroom could be updated but was clean and everything worked!"
Reviewed on Oct 9, 2026
The Windsor Suites
1700 Ben Franklin Pkwy Philadelphia PA
CA $202
CA $235 total
Oct 28 - Oct 29
includes taxes & fees
8.8/10 Excellent! (3,311 reviews)
"I had a really good time at this hotel. It was clean. Staff was friendly. The floors were amazing. The walls were amazing. The bathroom was nice like I can’t keep Raving about it!!! I will definitely be going back."
Reviewed on Oct 8, 2026
Motto by Hilton Philadelphia Rittenhouse Square
31 S 19th St Philadelphia PA
Fully refundableReserve now, pay when you stay
CA $143
CA $166 total
Nov 1 - Nov 2
includes taxes & fees
9/10 Wonderful! (2,527 reviews)
"The bathroom was super clean by any means and I had a sewer smell coming from the shower for almost all my stay. While not a game changer, the hair dryer only worked on one speed setting, not two. All and all it was fine, just not really clean with a stinky shower."
Reviewed on Oct 8, 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 $1,217. 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.
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.
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.
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.
Wyncote Golf Club
Enjoy a round of golf in Oxford at Wyncote Golf Club. Discover the area's waterfalls and spas.
Eagleview Town Center
7.6/10 (7 reviews)
You can browse for the perfect souvenirs at Eagleview Town Center during your trip to Exton. Check out the shops and top-notch restaurants in this family-friendly area.
What to do in Chester County
LEGOLAND® Discovery Center Philadelphia
CA $35
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
