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

  • Rest easy

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

Top Holiday Package Deals in Chestnut Hill

Price found within the past 48 hours. Click for updated prices.
One Sky Loft

One Sky Loft

2 out of 5
Center City
Price was CA $1,033, price is now CA $926 per person
CA $926
per person
Jan 15 - Jan 17
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to Philadelphia (PHL)
9.2/10 Wonderful! (150 reviews)
Highly recommend this place to stay! It had everything we needed! Will stay again if it is available when I am in Philly!

Reviewed on Oct 31, 2026

Orchard Way

Orchard Way

2 out of 5
Save 100% on your flight
Price was CA $5,369, price is now CA $3,662 per person
CA $3,662
per person
Dec 24 - Dec 28
found 12 hours ago
Roundtrip flight included
Montreal (YUL) to Philadelphia (PHL)
No reviews

Hotel Anna & Bel

Hotel Anna & Bel

4 out of 5
North Philadelphia
Price was CA $1,434, price is now CA $1,224 per person
CA $1,224
per person
Jan 15 - Jan 17
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to Philadelphia (PHL)
9.6/10 Exceptional! (190 reviews)

Plumsteadville Inn

Plumsteadville Inn

3 out of 5
Price was CA $1,219, price is now CA $1,056 per person
CA $1,056
per person
Dec 13 - Dec 17
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
9/10 Wonderful! (610 reviews)
Beautiful historic property, lovely room and comfortable. Very nice restaurant and bar on the premises.

Reviewed on Oct 31, 2026

Hyatt Centric Rittenhouse Square Philadelphia

Hyatt Centric Rittenhouse Square Philadelphia

4 out of 5
Center City
Price was CA $1,036, price is now CA $935 per person
CA $935
per person
Jan 15 - Jan 17
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to Philadelphia (PHL)
9.4/10 Exceptional! (1,790 reviews)

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
A large, golden bell with inscriptions, mounted on a structure with a historic building in the background.

Center City

3 out of top 10 points of interest in this area

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
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Nov 3 to Nov 4
CA $186
CA $216 total
Nov 3 - Nov 4
includes taxes & fees
9/10 Wonderful! (4,864 reviews)
"TV didn’t work and shower had a leak. Someone fixed the TV and they came right away."

Reviewed on Nov 1, 2026

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 $136 per night from Nov 23 to Nov 24
CA $136
CA $159 total
Nov 23 - Nov 24
includes taxes & fees
Doubletree by Hilton Philadelphia Airport
Motto by Hilton Philadelphia Rittenhouse Square

Motto by Hilton Philadelphia Rittenhouse Square

3.5 out of 5
31 S 19th St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Nov 23 to Nov 24
CA $113
CA $132 total
Nov 23 - Nov 24
includes taxes & fees
Motto by Hilton Philadelphia Rittenhouse Square
See all 3,070 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 CA $926, 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.

Stay near popular Chestnut Hill attractions

Morris Arboretum

6.8/10 (6 reviews)
Stroll among ancient trees, wetland tours and garden displays, in this peaceful setting that offers a reprieve from urban sightseeing.
See properties

Things to do

LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

CA $35
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions

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

CA $83
per adult
82% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
Double Decker Hop-On Hop-Off City Sightseeing Philadelphia

Double Decker Hop-On Hop-Off City Sightseeing Philadelphia (1, 2, or 3-Day)

CA $69
per adult
92% of travellers recommend
Double Decker Hop-On Hop-Off City Sightseeing Philadelphia (1, 2, or 3-Day)
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.