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*

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

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Top Holiday Package Deals in Chestnut Hill

Price found within the past 48 hours. Click for updated prices.
Towneplace Suites Cranbury South Brunswick

Towneplace Suites Cranbury South Brunswick

3 out of 5
Price was CA $819, price is now CA $714 per person
CA $714
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
9.2/10 Wonderful! (507 reviews)
.

Reviewed on Jun 14, 2026

The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Center City
Price was CA $2,003, price is now CA $1,585 per person
CA $1,585
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9.6/10 Exceptional! (1,002 reviews)
The hotel staff was professional, helpful, facility clean, love the breakfast menu, and I like the nice park in front of the hotel, and I out door patio next to the gym.

Reviewed on Jul 6, 2026

New Season Royals

New Season Royals

2 out of 5
Price was CA $1,193, price is now CA $978 per person
CA $978
per person
Aug 7 - Aug 9
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Philadelphia (PHL)
9.2/10 Wonderful! (144 reviews)
Very clean room and comfy bed. Great amenities. Thank You for having us.

Reviewed on Jun 21, 2026

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 $1,065, price is now CA $912 per person
CA $912
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
8.8/10 Excellent! (1,297 reviews)
The TV did not work well. Over all fine stay.

Reviewed on Jul 5, 2026

Loews Philadelphia Hotel

Loews Philadelphia Hotel

4 out of 5
Center City
Price was CA $1,017, price is now CA $872 per person
CA $872
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9.2/10 Wonderful! (1,860 reviews)
The hotel was in a pristine location. We truly enjoyed our stay. All the staff were superb.

Reviewed on Jul 5, 2026

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
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

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 $267 per night from Jul 20 to Jul 21
CA $267
CA $311 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (2,117 reviews)
"Location!"

Reviewed on Jul 5, 2026

Philadelphia Marriott Downtown
Sofitel Philadelphia at Rittenhouse Square

Sofitel Philadelphia at Rittenhouse Square

4.5 out of 5
120 S 17th St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Jul 23 to Jul 24
CA $227
CA $311 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (2,444 reviews)
"I arrived very late. At checked in, the customer service agent noticed my reservation was for the next day. He checked the room rate for that night, it was close to $1K and suggested for me to check online since I still have 10 minutes before midnights. I did managed to get a room at a similar rate ..."

Reviewed on Jul 5, 2026

Sofitel Philadelphia at Rittenhouse Square
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 $181 per night from Jul 7 to Jul 8
CA $181
CA $210 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (4,697 reviews)
"Overall, a positive experience staying at a great location in Philly. We were there during a heat wave but there was never an issue with the AC, there was filtered water available in the lobby and down the hall, coffee was available on demand in the lobby. There is limited parking on the street, ..."

Reviewed on Jul 5, 2026

Club Quarters Hotel Rittenhouse Square, Philadelphia
See all 3,179 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
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Family Vacations

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
Perhaps less than you imagined — from only CA $714, 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
Center City Philadelphia Food Tour with Reading Market

Center City Philadelphia Food Tour with Reading Market

CA $82
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 $82
per adult
82% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
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.