Chesterbrook Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.

Top Chesterbrook Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Valley Forge Casino Resort

Valley Forge Casino Resort

4 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.2/10 Very Good! (1,006 reviews)
beautiful casino but not much choice on food on a tuesday should have said restaurants only open on weekend - had to leave the property for dinner

Reviewed on Aug. 15, 2025

Guild House Hotel

Guild House Hotel

3 out of 5
Center City
per person
Nov 6 - Nov 9
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9.8/10 Exceptional! (43 reviews)
Gorgeous room. Wonderful amenities. Even the water pressure in the shower was fantastic. I felt like I was staying in an art gallery.

Reviewed on Jul. 20, 2025

The Bellevue Hotel, in The Unbound Collection by Hyatt

The Bellevue Hotel, in The Unbound Collection by Hyatt

4.5 out of 5
Center City
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.4/10 Very Good! (1,008 reviews)
Luxurious, vintage, classy. We were given drink vouchers.

Reviewed on Aug. 1, 2025

Hilton Philadelphia at Penn's Landing

Hilton Philadelphia at Penn's Landing

4 out of 5
Center City
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.2/10 Very Good! (1,309 reviews)
The riverfront will eventually be a better place to stay, but it’s currently under construction

Reviewed on Aug. 14, 2025

The Warwick Hotel Rittenhouse Square Philadelphia

The Warwick Hotel Rittenhouse Square Philadelphia

4 out of 5
Center City
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
7.8/10 Good! (1,528 reviews)
Rooms were pretty dated, shower in not great condition. Staff super nice and helpful.

Reviewed on Jul. 20, 2025

Ready to book your vacation to Chesterbrook?

 

Choose your dates

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
The price is CA $126 per night from Aug 17 to Aug 18
CA $126
CA $147 total
Aug 17 - Aug 18
includes taxes & 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
The price is CA $162 per night from Sep 14 to Sep 15
CA $162
CA $188 total
Sep 14 - Sep 15
includes taxes & fees
7.2/10 Good! (3,455 reviews)
"The bed was very comfortable. The grounds were very comfortable and relaxing. The lobby was very elegant."

Reviewed on Aug. 13, 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
The price is CA $198 per night from Aug 31 to Sep 1
CA $198
CA $231 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very Good! (1,333 reviews)
"N/a"

Reviewed on Aug. 13, 2025

Hilton Philadelphia at Penn's Landing
See all 2,734 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Chesterbrook

Rittenhouse Square

Rittenhouse Square

Rittenhouse Square is just one of the places to see in Philadelphia, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed theater scene in this vibrant area.

Rittenhouse Square
Philadelphia Museum of Art which includes art

Philadelphia Museum of Art

One of the country’s largest museums, with hundreds of thousands of objects, a Rodin Museum, renowned impressionist art and a sculpture garden.

Philadelphia Museum of Art
Liberty Bell Center showing a city, a monument and heritage architecture

Liberty Bell Center

Set in the historical heart of the city, this glass pavilion that houses America’s symbol of independence is one of the most visited sights in Philadelphia.

Liberty Bell Center

What to do in Chesterbrook

Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

CA $41
per traveller
Liberty, Freedom, and Revolution: American History Tours Bundle
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions

Go City: Philadelphia All-Inclusive Pass with 30+ Attractions

CA $81
per adult
80% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
Polaris Slingshot Rental-Philadelphia, PA

Polaris Slingshot Rental-Philadelphia, PA

CA $343
per traveller
Polaris Slingshot Rental-Philadelphia, PA
See all activities in Chesterbrook

Frequently asked questions

How much does a Chesterbrook vacation package cost?
You'll find cheap prices from CA $893 on Expedia for your Chesterbrook getaway. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Chesterbrook costs.
What are the cheapest months to go to Chesterbrook?
You can typically find lower rates and better availability in December, January and February. Check out our cheap Chesterbrook vacation packages and you could land some great off-season deals.
How many days is enough for Chesterbrook?
For your Chesterbrook vacation, a few days will be enough to tour the top spots. Make sure to check out Historic Sugartown — it's one of the main attractions in this destination. If you're looking for more adventure, think about basing yourself here and going on some trips from Chesterbrook.
How to find the best Chesterbrook package deals?
Bagging a cheap Chesterbrook package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a few filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Chesterbrook package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chesterbrook vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging accommodations and flights individually. Better still, you can customize your Chesterbrook escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
How to plan a trip to Chesterbrook?

  1. Pick your dates: What you want to do in Chesterbrook and your favourite season will help you decide when to get away.
  2. Set your budget: Factor in costs like flights, food and transportation when calculating how much to save for your trip to Chesterbrook. Then, choose a property that matches your budget, whether that's an economical stay or a lavish getaway.
  3. Set the duration of your trip: Start by compiling a list of the attractions and activities you want to experience in Chesterbrook. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your airfare and accommodations: Once you've settled on your dates and duration, lock in the ideal Chesterbrook vacation package for you.

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