Chesterbrook Vacations from $354

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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.
Hyatt Centric Center City Philadelphia

Hyatt Centric Center City Philadelphia

4 out of 5
Center City
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
9.4/10 Exceptional! (1,404 reviews)
My daughter & I came into town for the Chris. Town concert and stayed at this hotel. Reception was phenomenal. Very informative & kind. The hotel room itself was very clean and modern. I highly recommend!

Reviewed on Aug 13, 2025

Oceanside Lodge

Oceanside Lodge

2.5 out of 5
Save 100% on your flight
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philadelphia (PHL)
6.2/10 (1,001 reviews)
Easy check in, very quiet, clean pool, clean area, and reasonable price.

Reviewed on Aug 13, 2025

Chateau Renault

Chateau Renault

4 out of 5
Save 100% on your flight
per person
Oct 18 - Oct 22
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philadelphia (PHL)
8.8/10 Excellent! (326 reviews)
The property was very nice but for the price i paid I was expecting a better and bigger pool.the water was cloudy and the pool very small, i did not find the bar or maybe it didnt have none and reception is really bad on everyones phone, i felt like i was back 20 yrs ago

Reviewed on Aug 4, 2025

Surrey Beach House

Surrey Beach House

2 out of 5
Save 100% on your flight
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philadelphia (PHL)
9.8/10 Exceptional! (38 reviews)
Our room was clean and comfortable. Good A/C, fan a bit loud. Enjoyed the code for entrance into property and room. Very efficient.

Reviewed on Jul 24, 2025

AVIA Residences on Lincoln- Extended Stay

AVIA Residences on Lincoln- Extended Stay

3 out of 5
per person
Oct 28 - Nov 1
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Philadelphia (PHL)
8.6/10 Excellent! (1,002 reviews)
Pool was great and made us happy with our decision to stay here. Full kitchen was perfect for our needs. Landscaping was done very well and had pretty flowers. The room was about 80% clean- there were details missed like a few hairs/dirty qtip in drawer and dusty bedframe. With limited office hours, later swims meant no swim towels available. Overall, property needs TLC.

Reviewed on Jul 6, 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

4.5/5(1,315 reviews)

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

Rittenhouse Square
Pennsylvania Convention Center

Pennsylvania Convention Center

4.5/5(875 reviews)

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

Pennsylvania Convention Center
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.

Wells Fargo Center

4.5/5(824 reviews)

Catch an event at Wells Fargo Center during your trip to Philadelphia. Experience the fascinating museums and great live music in this vibrant area.

Wells Fargo Center

What to do in Chesterbrook

Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

$30
per traveler
Liberty, Freedom, and Revolution: American History Tours Bundle
Polaris Slingshot Rental-Philadelphia, PA

Polaris Slingshot Rental-Philadelphia, PA

$250
per traveler
Polaris Slingshot Rental-Philadelphia, PA
Philadelphia: The Franklin Institute Entry Ticket

Philadelphia: The Franklin Institute Entry Ticket

$29
per adult
Philadelphia: The Franklin Institute Entry 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
$104 nightly
The price is $121 total per night from Aug 17 to Aug 18
$121 total
Aug 17 - Aug 18
Total includes taxes and fees
8.8/10 Excellent! (4,049 reviews)
"I booked by mistake for the 25.08 25 to 26.08.25 Itinerary # 73204530703699 please could arrange the refund View full itinerary Traveller details Adults, 2 Club Quarters Hotel Rittenhouse Square, Philadelphia   1628"

Reviewed on Aug 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
$118 nightly
The price is $137 total per night from Aug 31 to Sep 1
$137 total
Aug 31 - Sep 1
Total includes taxes and fees
7.2/10 Good! (3,454 reviews)
"Excellent"

Reviewed on Aug 11, 2025

Doubletree by Hilton Philadelphia Airport
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
$144 nightly
The price is $167 total per night from Aug 31 to Sep 1
$167 total
Aug 31 - Sep 1
Total includes taxes and fees
8/10 Very Good! (1,331 reviews)
"The fooms are old rhe carpet needs replacing. Everything else was great. The 20 buffet was sad...it dhiuld be free for the food the s er ve you"

Reviewed on Aug 11, 2025

Hilton Philadelphia at Penn's Landing
See all 2,736 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.

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Frequently asked questions

How much does a Chesterbrook vacation package cost?
Offering great value package deals from $354 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.