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.
The Windsor Suites

The Windsor Suites

4 out of 5
Center City
Price was CA $2,124, price is now CA $1,659 per person
CA $1,659
per person
Jun 18 - Jun 21
found 12 hours ago
Roundtrip flight included
Winnipeg (YWG) to Philadelphia (PHL)
8.6/10 Excellent! (2,799 reviews)
Great location, large rooms, friendly staff. Disappointed that the restaurants next door don’t open for breakfast on Monday, Tuesday or Wednesday.

Reviewed on May 8, 2026

The Bellevue Hotel - The Unbound Collection by Hyatt

The Bellevue Hotel - The Unbound Collection by Hyatt

4.5 out of 5
Center City
Price was CA $2,478, price is now CA $1,936 per person
CA $1,936
per person
Jun 18 - Jun 21
found 12 hours ago
Roundtrip flight included
Winnipeg (YWG) to Philadelphia (PHL)
8.6/10 Excellent! (1,003 reviews)
Lovely room and hotel. Housekeeping did not come. Arrived late afternoon and no one was available to help with luggage. Family loved the exercise/spa area. Room was quick for breakfast, food was good but I was not expecting it to come on a cart or tray, not bags

Reviewed on May 8, 2026

The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Center City
Price was CA $2,804, price is now CA $2,223 per person
CA $2,223
per person
Jul 30 - Aug 2
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Philadelphia (PHL)
9.6/10 Exceptional! (993 reviews)
Great place to stay, amazing location and view of the park.

Reviewed on Apr 28, 2026

Kimpton Hotel Palomar Philadelphia by IHG

Kimpton Hotel Palomar Philadelphia by IHG

4.5 out of 5
Center City
Price was CA $2,241, price is now CA $1,801 per person
CA $1,801
per person
Jul 30 - Aug 2
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Philadelphia (PHL)
9/10 Wonderful! (1,130 reviews)
Centrally located with sightseeing and dining options, comfortable rooms though ours showed its age, can hear street noise in the morning - we were on the 7th floor.

Reviewed on May 6, 2026

Canopy by Hilton Philadelphia Center City

Canopy by Hilton Philadelphia Center City

4 out of 5
Center City
Price was CA $2,601, price is now CA $2,101 per person
CA $2,101
per person
Jul 30 - Aug 2
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Philadelphia (PHL)
9.4/10 Exceptional! (1,924 reviews)
I like that they renovated an older building. The chairs in the lobby were filthy. Good location.

Reviewed on May 8, 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 Jun 2 to Jun 3
CA $201
CA $223 total
Jun 2 - Jun 3
includes taxes & fees
9/10 Wonderful! (905 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 $141 per night from May 10 to May 11
CA $141
CA $164 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (4,548 reviews)
Small rooms

Reviewed on May 8, 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 $245 per night from May 25 to May 26
CA $245
CA $285 total
May 25 - May 26
includes taxes & fees
Philadelphia Marriott Downtown
See all 3,012 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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All Inclusive Vacations
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Discover the most popular places to visit in Chesterbrook

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
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
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
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
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
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.