Chester County Vacation Packages

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Top vacation destinations in Chester County

West Chester which includes a small town or village and café scenes
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West Chester

West Chester
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Kennett Square

Kennett Square

Top Chester County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Shawnee Village Resort

Shawnee Village Resort

2.5 out of 5
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Allentown (ABE)
8.2/10 Very Good! (982 reviews)
Our unit wasn't updated but it was clean and comfortable. It had an old fashioned kind of rustic look. We had an issue with ants upon arrival but maintenance was sent out immediately to fix the problem. The water wasn't always hot but maybe it was because there were 5 of us! We made use of the pools, hot tub and game rooms during our stay. The restaurants and supermarkets were all 15 minutes drive away. Overall i would rate our visit a 6 out of 10.

Reviewed on Aug. 4, 2025

Countryside Cottages

Countryside Cottages

3 out of 5
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Allentown (ABE)
9.4/10 Exceptional! (30 reviews)
Very peaceful environment. The creek was behind our cabin and the sound of sleeping was soothing. Firewood was available to purchase for an indoor or outdoor fire in which we did. Beautiful get away to regroup from the hustle of the city. Very friendly and perfect for families. Will definitely come back.

Reviewed on May 28, 2025

Slopeside Escape by Avantstay Walk to Ski Lifts Arcade Games + Shuffleboard

Slopeside Escape by Avantstay Walk to Ski Lifts Arcade Games + Shuffleboard

3 out of 5
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Allentown (ABE)
10/10 Exceptional! (3 reviews)
Our family enjoy a great time sharing fun, games, good food and a fantastic place to every night a good surprise. The home was spotless, organized, and had plenty of surprises. From a heated bathroom, to old time acrade games, to an adjustable bed. The children did not want to leave their Mario theme room. I am looking forward to a return trip.

Reviewed on Jul. 22, 2025

Camelback Lodge & Aquatopia Indoor Waterpark

Camelback Lodge & Aquatopia Indoor Waterpark

3.5 out of 5
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Allentown (ABE)
8.2/10 Very Good! (2,123 reviews)
Overall experience was great. Nice place for the kids to burn engery anf have fun while doing so. Only issue is our bands didnt work to get into room at first. Had to go back to the front desk to reactivate each handband.

Reviewed on Aug. 7, 2025

Chateau Resort & Conference Center

Chateau Resort & Conference Center

3 out of 5
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Allentown (ABE)
7.2/10 Good! (1,008 reviews)
Resort clean and stay enjoyable. Pool, decks, grounds and at night so picturesq, calming and beautiful.

Reviewed on Aug. 8, 2025

Chester County Hotel Deals

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 $126 per night from Aug 17 to Aug 18
CA $126
CA $146 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (4,023 reviews)
"Definitely one of the best hotels I’ve stayed at. All around convenient and cleanliness!"

Reviewed on Aug. 6, 2025

Club Quarters Hotel Rittenhouse Square, Philadelphia
Hilton Philadelphia at Penn's Landing

Hilton Philadelphia at Penn's Landing

4 out of 5
201 S. Christopher Columbus Blvd, Philadelphia, PA
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Aug 31 to Sep 1
CA $197
CA $230 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very Good! (1,306 reviews)
"Great job!"

Reviewed on Aug. 7, 2025

Hilton Philadelphia at Penn's Landing
Sonesta Philadelphia Rittenhouse Square

Sonesta Philadelphia Rittenhouse Square

4 out of 5
1800 Market St, Philadelphia, PA
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Aug 31 to Sep 1
CA $136
CA $190 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (1,872 reviews)
"Solid place all around. Nice rooftop as well."

Reviewed on Aug. 6, 2025

Sonesta Philadelphia Rittenhouse Square
See all 4,236 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.
All Inclusive Vacations
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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 $706. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.