Chesterbrook Vacation Packages

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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.

Top Chesterbrook Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

3 out of 5
Center City
Price was CA $2,217, price is now CA $1,662 per person
CA $1,662
per person
May 14 - May 18
found 22 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Philadelphia (PHL)
8.8/10 Excellent! (1,092 reviews)
I only stayed at this hotel for one night, the staff was friendly and the location was great in downtown Philly. I did valet parking for my car but there are two parking lots very close by. The rooms are small, but we managed ok.

Reviewed on Mar 31, 2026

Orchard Way

Orchard Way

2 out of 5
Price was CA $4,092, price is now CA $2,474 per person
CA $2,474
per person
Jun 20 - Jun 23
found 1 hour ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philadelphia (PHL)
No reviews
Valley Forge Casino Resort

Valley Forge Casino Resort

4 out of 5
Price was CA $3,099, price is now CA $1,938 per person
CA $1,938
per person
May 14 - May 18
found 22 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Philadelphia (PHL)
8.4/10 Very Good! (1,096 reviews)
No hot water. The hotel seemed understaffed. They were not available.

Reviewed on Mar 29, 2026

1BR Passyunk AveStunner-Perfect Location

1BR Passyunk AveStunner-Perfect Location

3.5 out of 5
South Philadelphia
Price was CA $5,905, price is now CA $4,080 per person
CA $4,080
per person
Jun 20 - Jun 23
found 1 hour ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philadelphia (PHL)
9.8/10 Exceptional! (9 reviews)
It was in a local neighborhood rather than a tourist area.

Reviewed on Jul 5, 2025

E Passyunk Ave 1BR Gem Prime Location

E Passyunk Ave 1BR Gem Prime Location

2.5 out of 5
South Philadelphia
Price was CA $4,426, price is now CA $3,346 per person
CA $3,346
per person
Jun 20 - Jun 23
found 1 hour ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philadelphia (PHL)
9.8/10 Exceptional! (6 reviews)
This property is a Philly gem. It is so cute and cozy. It is updated and has the convenience of home. The washer and dryer were a plus as well. Gabe and Jon are great hosts and communication with them was easy, as they got back to me in a timely manner. We will definitely stay there on our next visit.

Reviewed on Feb 15, 2025

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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 $155 per night from Apr 5 to Apr 6
CA $155
CA $180 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (4,428 reviews)
Air conditioning was great! The construction in the front was unpleasant. Overall clean room

Reviewed on Apr 1, 2026

Club Quarters Hotel Rittenhouse Square, Philadelphia
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 $148 per night from Apr 5 to Apr 6
CA $148
CA $172 total
Apr 5 - Apr 6
includes taxes & fees
8.8/10 Excellent! (2,695 reviews)
The air wasn’t working properly in either room. The service and balcony took care of that! We will be back again!!!

Reviewed on Apr 1, 2026

The Windsor Suites
Wyndham Philadelphia Historic District

Wyndham Philadelphia Historic District

3.5 out of 5
400 Arch Street Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Apr 7 to Apr 8
CA $178
CA $207 total
Apr 7 - Apr 8
includes taxes & fees
8.2/10 Very Good! (3,538 reviews)
N/a

Reviewed on Apr 1, 2026

Wyndham Philadelphia Historic District
See all 2,933 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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Discover the most popular places to visit in Chesterbrook

Rittenhouse Square

Rittenhouse Square

4.5/5(41 reviews)

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 acclaimed theater scene and great live music in this vibrant area.

Rittenhouse Square
Aerial of Theme Park

Sesame Place

4/5(13 reviews)

Bring the kids to Sesame Place and enjoy the excitement of this theme park in Oxford Valley. Attend a sporting event in this quaint area.

Sesame Place
Philadelphia Museum of Art

Philadelphia Museum of Art

4.5/5(104 reviews)

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

What to do in Chesterbrook

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

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

CA $81
per adult
82% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
Go City: Philadelphia Explorer Pass - Choose 3 to 7 Attractions

Go City: Philadelphia Explorer Pass - Choose 3 to 7 Attractions

CA $81
per adult
76% of travellers recommend
Go City: Philadelphia Explorer Pass - Choose 3 to 7 Attractions
Sphinx Gallery

Penn Museum Admission Ticket

CA $31
per adult
100% of travellers recommend
Penn Museum Admission Ticket
See all activities in Chesterbrook

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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.