Chesterbrook Vacations from $326

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Your Chesterbrook Vacation

Get ready to experience Chesterbrook on your terms with a custom Chesterbrook vacation package! Discovering the treasures of this interesting city is made simpler with a base in a neighborhood such as Gladwyne, which is good for golfing, among lots of other things. Eager to explore your new surroundings? Chanticleer Garden, Wayne Art Center and Chester Valley Trail Trailhead are just three of the most popular places to visit during a trip to Chesterbrook. Browse Expedia's extensive range of travel options and begin planning your dream vacation to Chesterbrook now.

The Latest Chesterbrook vacation packages

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel Rittenhouse Square, Philadelphia

Club Quarters Hotel Rittenhouse Square, Philadelphia

4 out of 5
Center City
Save 100% on your flight
Price was $501, price is now $326 per person
$326
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
8.8/10 Excellent! (4,159 reviews)
Excellent hotel. Great staff and super clean rooms. Great location.

Reviewed on Nov 13, 2025

Canopy by Hilton Philadelphia Center City

Canopy by Hilton Philadelphia Center City

4 out of 5
Center City
Save 100% on your flight
Price was $827, price is now $504 per person
$504
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
9.2/10 Wonderful! (1,868 reviews)
The room was actually missing the steamer, bathroom garbage can and jad a completely empty bottle of body wash in the shower on the day of my arrival. A call to the front desk did remedy that after awhile. Otherwise, the room was clean and the floor was very quiet. Front desk staff were friendly.

Reviewed on Nov 9, 2025

Sheraton Philadelphia Downtown

Sheraton Philadelphia Downtown

4 out of 5
Center City
Save 100% on your flight
Price was $603, price is now $380 per person
$380
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
8.4/10 Very Good! (1,010 reviews)
Staff at hotel was really nice. They helped us find places to visit. Great experience!!

Reviewed on Nov 11, 2025

The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Center City
Save 100% on your flight
Price was $1,319, price is now $840 per person
$840
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
9.6/10 Exceptional! (905 reviews)
Nice room and staffs are helpful.

Reviewed on Nov 9, 2025

Doubletree by Hilton Philadelphia Airport

Doubletree by Hilton Philadelphia Airport

4 out of 5
Southwest Philadelphia
Save 100% on your flight
Price was $538, price is now $349 per person
$349
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
7.4/10 Good! (3,785 reviews)
Front desk ladies are not very pleasant at first you have to speak first and warm them up Not pleasantly or welcoming. At first.after u get pass that its all good...

Reviewed on Nov 13, 2025

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Discover the most popular places to visit in Chesterbrook

Rittenhouse Square which includes street scenes and a park

Rittenhouse Square

Relax on grassy lawns, browse interesting sculptures and attend vibrant festivals at this historic square and popular city gathering point.

Rittenhouse Square
If you can, get club box seats at the Flyers game for a great view and intimate bar and private restrooms, away from the crowds.

Xfinity Mobile Arena

Catch an event at Xfinity Mobile Arena during your trip to Philadelphia. Experience the great live music and fascinating museums in this vibrant area.

Xfinity Mobile Arena
Pennsylvania Convention Center

Pennsylvania Convention Center

During your trip, find out what's happening at Pennsylvania Convention Center, a top convention center in Philadelphia. Experience the great live music or attend a sporting event in this vibrant area.

Pennsylvania Convention Center

What to do in Chesterbrook

Philadelphia: Museum of Illusions Timed Entrance Ticket

Philadelphia: Museum of Illusions Timed Entrance Ticket

$31
per adult
98% of travellers recommend
Philadelphia: Museum of Illusions Timed Entrance Ticket
LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

$25
per adult
82% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
Sphinx Gallery

Penn Museum Admission Ticket

$18
per adult
100% of travellers recommend
Penn Museum Admission Ticket
See all activities in Chesterbrook

Chesterbrook 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
$108 nightly
The price is $126 total per night from Dec 3 to Dec 4
$126 total
Dec 3 - Dec 4
Total with taxes and fees
8.8/10 Excellent! (4,171 reviews)
Location is perfect

Reviewed on Nov 12, 2025

Club Quarters Hotel Rittenhouse Square, Philadelphia
Doubletree by Hilton Philadelphia Airport

Doubletree by Hilton Philadelphia Airport

4 out of 5
4509 Island Ave, Philadelphia, PA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $129 total per night from Dec 7 to Dec 8
$129 total
Dec 7 - Dec 8
Total with taxes and fees
7.4/10 Good! (3,921 reviews)
Staff was very nice, older hotel needs updating. First room was filthy but they changed me to a cleaner one. Beds extremely comfortable which was a huge plus. Never heard any planes which was a plus as well. They should write parking fees on the site and not just parking available. Wasn’t expecting ...

Reviewed on Nov 12, 2025

Doubletree by Hilton Philadelphia Airport
Sheraton Suites Philadelphia Airport

Sheraton Suites Philadelphia Airport

3.5 out of 5
4101b Island Ave, Philadelphia, PA
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $150 total per night from Nov 24 to Nov 25
$150 total
Nov 24 - Nov 25
Total with taxes and fees
8.4/10 Very Good! (1,762 reviews)
Yes

Reviewed on Nov 11, 2025

Sheraton Suites Philadelphia Airport
See all 2,968 properties in Chesterbrook
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.

Find the Best Chesterbrook Vacation Packages

Chesterbrook Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Philadelphia Intl. Airport (PHL)
Population
4,600
Top Sights
Villanova University, Chanticleer Garden and Chester Valley Trail Trailhead

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Frequently asked questions

How much does a Chesterbrook vacation package cost?
Offering great value package deals from $326 on Expedia, you'll be surprised at how little a vacation to Chesterbrook costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chesterbrook?
January, February and March are great times to search for cheap Chesterbrook vacation packages. Traveling in less busy months means you can typically find lower prices on flights and hotels.
How many days is enough for Chesterbrook?
With a well-organized schedule, you can easily hit the most popular Chesterbrook sights in a handful of days. But if you prefer to discover hidden gems or go on day trips, think about booking your Chesterbrook vacation for longer.
How to find the best Chesterbrook package deals?
Start your search for a Chesterbrook package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Chesterbrook package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chesterbrook adventure off to a flying start.
Is it cheaper to book a Chesterbrook vacation as a package?
You can enjoy significant savings on your Chesterbrook getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chesterbrook?
Score incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Chesterbrook escape.
Does Expedia offer Book Now, Pay Later Chesterbrook vacation packages?
If you're like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Chesterbrook trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.