Chester County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • 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

FlightsFlightsHotelsHotels

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.
Chateau Resort & Conference Center

Chateau Resort & Conference Center

3 out of 5
Price was CA $806, price is now CA $691 per person
CA $691
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Allentown (ABE)
7.4/10 Good! (1,017 reviews)
Nice Mountain View from the balcony Love it

Reviewed on May 18, 2026

Prime Location on Camelback Mtn, Renovated w/ Movie & Game Room The Bear's Den

Prime Location on Camelback Mtn, Renovated w/ Movie & Game Room The Bear's Den

3 out of 5
Price was CA $1,260, price is now CA $1,070 per person
CA $1,070
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Allentown (ABE)
8.4/10 Very Good! (5 reviews)
The place was very close to camelback activities and the outlets. Please was great.

Reviewed on Apr 5, 2026

Sunbird Lodge by Avantstay Gated Community + Indoor Pool Access + Fitness Center + Tennis Court

Sunbird Lodge by Avantstay Gated Community + Indoor Pool Access + Fitness Center + Tennis Court

3 out of 5
Price was CA $1,306, price is now CA $1,119 per person
CA $1,119
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Allentown (ABE)
No reviews
Timberline Retreat by Avantstay Forest Views & Minutes to Camelback Resort

Timberline Retreat by Avantstay Forest Views & Minutes to Camelback Resort

3 out of 5
Price was CA $1,120, price is now CA $964 per person
CA $964
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Allentown (ABE)
9/10 Wonderful! (4 reviews)
Nice place to stay. Recommended and good attention.

Reviewed on Jan 12, 2026

Baymont by Wyndham Bartonsville Poconos

Baymont by Wyndham Bartonsville Poconos

2.5 out of 5
Price was CA $830, price is now CA $734 per person
CA $734
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Allentown (ABE)
8.2/10 Very Good! (1,537 reviews)
I have stayed there multiple times and never disappointed.

Reviewed on May 25, 2026

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 $165 per night from Jun 7 to Jun 8
CA $165
CA $192 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (4,586 reviews)
"The room was quite small. We had to pay extra to check in early even though there was an available room. Mostly, the property was run down (there was a hole in the curtain that looked like a cigarette burn), the bathroom smelled like sewage, the cleaners weren’t very thorough (left several pieces ..."

Reviewed on May 25, 2026

Club Quarters Hotel Rittenhouse Square, Philadelphia
Philadelphia Marriott Downtown

Philadelphia Marriott Downtown

4 out of 5
1201 Market St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from May 28 to May 29
CA $289
CA $336 total
May 28 - May 29
includes taxes & fees
8.6/10 Excellent! (1,991 reviews)
"Great hot water and nice comfy bed."

Reviewed on May 25, 2026

Philadelphia Marriott Downtown
The Windsor Suites

The Windsor Suites

4 out of 5
1700 Ben Franklin Pkwy Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from May 26 to May 27
CA $208
CA $242 total
May 26 - May 27
includes taxes & fees
8.6/10 Excellent! (2,861 reviews)
"Pros: staff was pleasant, the security staff took their job seriously, the bed was comfortable Cons: insulation in between rooms was horrible, hallways smelt musty and like food, bathroom (shower) was dirty"

Reviewed on May 25, 2026

The Windsor Suites
See all 4,555 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.
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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 $691. 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.