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.
YOWIE (Hotel & Shop)

YOWIE (Hotel & Shop)

2 out of 5
South Philadelphia
Price was CA $2,440, price is now CA $1,766 per person
CA $1,766
per person
Jun 24 - Jun 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
9.8/10 Exceptional! (70 reviews)
Get a room facing the street, not the wall!

Reviewed on Apr 17, 2026

Cozy Home near City Center with Hot tub

Cozy Home near City Center with Hot tub

3 out of 5
South Philadelphia
Price was CA $11,671, price is now CA $6,085 per person
CA $6,085
per person
Jun 24 - Jun 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
10/10 Exceptional! (3 reviews)
This was the perfect place for my group and our needs. Enough beds with options; a dark, quiet room in the basement, a shared room with a two full beds, the top floor king size suite, even a pull out sofa! All useful accommodations for a party of 5 or more. To top it off, the roof top hot tub with a city skyline view was incredible! It was a great location too, in walking distance to our venue in South Philly. Everything worked out perfectly, and I'm grateful that this option was available. Thank you!

Reviewed on Mar 2, 2026

Casa De Miliki

Casa De Miliki

2 out of 5
South Philadelphia
Price was CA $7,492, price is now CA $4,740 per person
CA $4,740
per person
Jun 24 - Jun 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
No reviews
Surrey Beach House

Surrey Beach House

2 out of 5
Price was CA $2,405, price is now CA $1,769 per person
CA $1,769
per person
Jun 17 - Jun 24
found 5 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Philadelphia (PHL)
9.8/10 Exceptional! (51 reviews)
Beautifully maintained, very clean, and wonderful location.

Reviewed on Apr 19, 2026

The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Center City
Price was CA $2,487, price is now CA $1,948 per person
CA $1,948
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
9.6/10 Exceptional! (994 reviews)
A good location for enjoying Philadelphia!

Reviewed on May 11, 2026

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Chesterbrook Hotel Deals

Embassy Suites by Hilton Philadelphia Valley Forge

Embassy Suites by Hilton Philadelphia Valley Forge

3.5 out of 5
888 Chesterbrook Blvd Wayne PA
The price is CA $201 per night from May 25 to May 26
CA $201
CA $223 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (906 reviews)
ALL ROUND GOOD.

Reviewed on May 4, 2026

Embassy Suites by Hilton Philadelphia Valley Forge
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 $152 per night from Jun 7 to Jun 8
CA $152
CA $177 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (4,569 reviews)
This is a 3* hotel not 4*

Reviewed on May 11, 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 $257 per night from May 26 to May 27
CA $257
CA $299 total
May 26 - May 27
includes taxes & fees
8.6/10 Excellent! (1,979 reviews)
.

Reviewed on May 11, 2026

Philadelphia Marriott Downtown
See all 2,967 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 art scene and entertainment choices in this vibrant area.

Rittenhouse Square
Aerial of Theme Park

Sesame Place

4/5(13 reviews)

Enjoy the rides and games at Sesame Place and find out why this is a popular theme park in Oxford Valley. Attend a sporting event in this family-friendly 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

Center City Philadelphia Food Tour with Reading Market

Center City Philadelphia Food Tour with Reading Market

CA $81
per adult
88% of travellers recommend
Center City Philadelphia Food Tour with Reading Market
BYOB Historically Hilarious Trolley Tour of Philadelphia

BYOB Historically Hilarious Trolley Tour of Philadelphia

CA $67
per adult
100% of travellers recommend
BYOB Historically Hilarious Trolley Tour of Philadelphia
LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

CA $34
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
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.