Chestnut Hill Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Aug 10 - Aug 15

    Sheraton Philadelphia Downtown + Flight

    Center City
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,017 reviews)
    "Great stay, a bit pricey; wish breakfast was included in the price. But overall good stay and service."
    Reviewed May 18, 2026
    Roundtrip • Toronto (YYZ) - Philadelphia (PHL)
    YYZ - PHL • Nonstop PHL - YYZ • Nonstop
    CA $1,628
    CA $1,327
    per traveller
    found 4 hours ago
    Sheraton Philadelphia Downtown
  • House, Garden View | Living area
    Jul 30 - Aug 2

    Orchard Way + Flight

    Yeadon
    3 nights
    2.0 star property
    Roundtrip • Calgary (YYC) - Philadelphia (PHL)
    YYC - PHL • 1 stop PHL - YYC • 1 stop
    CA $4,266
    CA $2,768
    per traveller
    found 6 hours ago
    Orchard Way
  • Terrace/patio
    Jul 30 - Aug 2

    Prime City Condo Parking + Skyline Views + Flight

    Center City
    3 nights
    3.0 star property
    Roundtrip • Calgary (YYC) - Philadelphia (PHL)
    YYC - PHL • 1 stop PHL - YYC • 1 stop
    CA $9,537
    CA $7,368
    per traveller
    found 6 hours ago
    Prime City Condo Parking + Skyline Views
  • Suite 303 Iconic Corner King | Living area
    Jul 30 - Aug 2

    YOWIE (Hotel & Shop) + Flight

    South Philadelphia
    3 nights
    2.0 star property
    9.8/10 - Exceptional (71 reviews)
    "Get a room facing the street, not the wall!"
    Reviewed April 17, 2026
    Roundtrip • Calgary (YYC) - Philadelphia (PHL)
    YYC - PHL • 1 stop PHL - YYC • 1 stop
    CA $2,138
    CA $1,656
    per traveller
    found 7 hours ago
    YOWIE (Hotel & Shop)
  • Premium Suite | Laundry
    Jul 30 - Aug 2

    One Sky Loft + Flight

    Center City
    3 nights
    2.0 star property
    9.4/10 - Exceptional (93 reviews)
    "The views from both balconies were fantastic and the place was very comfortable and clean. Very safe and secure feeling in the heart of the historic district. The bed and bedding were very comfortable, and the apartment was equipped with everything needed to relax and enjoy a break between historic sites and shows."
    Reviewed May 18, 2026
    Roundtrip • Montreal (YUL) - Philadelphia (PHL)
    YUL - PHL • Nonstop PHL - YUL • Nonstop
    CA $1,852
    CA $1,444
    per traveller
    found 5 hours ago
    One Sky Loft

Where to stay in Chestnut Hill

Find the best Chestnut Hill areas and neighborhoods for the activities you enjoy most. Learn more about Chestnut Hill
Center City

Center City

2 out of top 10 points of interest in this area
4.5/5(210 area reviews)

Boasting a dense downtown area, Center City offers a plethora of restaurants, bars, and cultural institutions like Kimmel Center and Academy of Music. Explore Penn's Landing, Old City, or the medical Mütter Museum, and enjoy convenient transport options.

Find hotels in Center City

Chestnut Hill Hotel Deals

Club Quarters Hotel Rittenhouse Square, Philadelphia

Club Quarters Hotel Rittenhouse Square, Philadelphia

4 out of 5
1628 Chestnut St Philadelphia PA
The price is CA $153 per night from May 25 to May 26
CA $153
CA $178 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (4,570 reviews)
"My reservation was guaranteed for 3:00 PM check-in. I arrived at 3:15 PM and my room was not ready. While one of the desk clerks was very apologetic, I had to wait until 3:40 before my room was ready; that is not acceptable. It really is a bare bones hotel where the only amenity is a coffee machine ..."

Reviewed on May 18, 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 $273 per night from May 24 to May 25
CA $273
CA $318 total
May 24 - May 25
includes taxes & fees
8.6/10 Excellent! (2,001 reviews)
"Sorry I had to give Marriott Hotel these “terrible” reviews… When you arrive at 23:00 and have an important appointment next morning, early morning that is, the last thing you want to hear from the Receptionist is that there are no rooms available for you, despite you have paid in advance for it. ..."

Reviewed on May 19, 2026

Philadelphia Marriott Downtown
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 $188 per night from May 25 to May 26
CA $188
CA $219 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (2,846 reviews)
"Nice staff - great location"

Reviewed on May 18, 2026

The Windsor Suites
See all 3,156 properties in Chestnut Hill
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

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
Perhaps less than you imagined — from only , in fact! By combining hotels, flights and car rentals into your own tailor-made travel package, your trip to Chestnut Hill is just a few clicks away.
How do I get a cheap travel package to Chestnut Hill?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, flights, rental cars and activities — we've got everything you need. Choose a combination that best suits you and watch your savings pile up. Of course, a package deal is never one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 hotel options from all over the world, which lets you customize your Chestnut Hill vacation.
Where should I stay in Chestnut Hill?
Most who travel to Chestnut Hill include Liberty Bell Center and Independence Hall on their itineraries. Why not choose a hotel right near these fantastic attractions?
What are the top hotels in Chestnut Hill?
Get your escape off to a good start by booking a stay at Chestnut Hill Cottage - Rest, Play And Explore. It's one of most popular properties in Chestnut Hill. Another welcoming option is Chestnut Hill Rental Home.
How far in advance should I book my Chestnut Hill vacation?
Your best bet is to book early. Air carriers generally advertise flights nearly 12 months prior to departure, and this is when you can pick up some rock-bottom prices. Just been told you need to take your vacation time next month? No sweat. Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Chestnut Hill travel package include?
Hotels, flights and car rentals — we bring you the best deals. All you have to do is pick and choose your favorite combination. After you've made your booking, you can add on the exciting stuff like sightseeing activities. Our travel packages make it easy to put together an awesome Chestnut Hill escape.
What should I know before booking a Chestnut Hill travel package?
When you book your flights, hotels and car rentals together, you'll score great discounts. Whether you're planning a beach break in a villa or want to stay in a cozy apartment in the city, Expedia can make it happen for less.
Can I choose my airline with a Chestnut Hill Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You can pick and choose your flights, hotels and more. We have access to more than 550 airline partners across the globe, so you have options galore when putting together your Chestnut Hill escape.
If I'm not able to travel, can I cancel my Chestnut Hill vacation package?
Because we understand life is full of surprises, the answer is yes. For further details, check out our Customer Service Portal. But generally speaking, if you've booked your Chestnut Hill vacation package in the last 24 hours, you may be able to change or cancel it for free. Your hotel, airline or car rental company may impose a fee if your booking is older than that.

Discover the most popular places to visit in Chestnut Hill

Morris Arboretum

Morris Arboretum

Stroll among ancient trees, wetland tours and garden displays, in this peaceful setting that offers a reprieve from urban sightseeing.

Morris Arboretum

Things to do

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 $66
per adult
100% of travellers recommend
BYOB Historically Hilarious Trolley Tour of Philadelphia
See all activities in Philadelphia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.