Chestnut Hill Holidays

Photo by Stewart Helfer

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

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

Known for its fascinating museums and acclaimed art galleries, there's plenty to explore in Center City. Check out top attractions like Pennsylvania Convention Center and Reading Terminal Market, and jump on the metro at 11th St Station or 8th St Station to see more of the city.

Find hotels in Center City
A statue of a woman holding a torch and a child, with a text plaque reading "Religious Liberty" dedicated to the people of the United States by the Order B'Nai B'rith and Israelites of America.

Old City

Known for its abundant dining options and interesting museums, there's plenty to explore in Old City. Top attractions like Betsy Ross House and Historic Arch Street Meeting House are major draws, and you can catch the metro at 2nd St. Station or 5th St. Station to see more of the city.

Find hotels in Old City
A nighttime pathway in a park with trees and buildings in the background.

Rittenhouse Square

While you're in Rittenhouse Square, take in top sights like Walnut Street or Rittenhouse Row, and hop on the metro to see more of the city at 15th-16th & Locust Station or 19th St Station.

Find hotels in Rittenhouse Square
A courtyard with a fountain, a bench, and a building with a Penn logo.

University City

1 out of top 10 points of interest in this area

Travellers choose University City for its ample dining options. Hop aboard the metro at Penn Medicine Station or 33rd St Station and check out top sights like Franklin Field.

Find hotels in University City
A street with a restaurant named South Philly Barbacoa.

South Philadelphia

3 out of top 10 points of interest in this area

Travellers choose South Philadelphia for its great live music. Hop aboard the metro at Snyder Station or Tasker Morris Station and check out top sights like Xfinity Mobile Arena.

Find hotels in South Philadelphia

Top hotels in Chestnut Hill

Club Quarters Hotel Rittenhouse Square, Philadelphia

Club Quarters Hotel Rittenhouse Square, Philadelphia

1628 Chestnut St Philadelphia PA
Fully refundableReserve now, pay when you stay
S$205
10 Sept - 11 Sept
includes taxes & fees
9/10 Wonderful! (4,849 reviews)
"One of the worst experiences I’ve ever had at a hotel. I had a woman go into my hotel room without permission and I asked for video footage and they told me that they didn’t find it. I’m pretty sure they just lied about it and things are missing for my room. Never stay here this place is ..."

Reviewed on 9 Sept, 2026

Club Quarters Hotel Rittenhouse Square, Philadelphia
The Windsor Suites

The Windsor Suites

1700 Ben Franklin Pkwy Philadelphia PA
S$176
20 Sept - 21 Sept
includes taxes & fees
8.8/10 Excellent! (3,215 reviews)
"The room was clean and the staff were very helpful."

Reviewed on 9 Sept, 2026

The Windsor Suites
Sofitel Philadelphia at Rittenhouse Square

Sofitel Philadelphia at Rittenhouse Square

120 S 17th St Philadelphia PA
Fully refundableReserve now, pay when you stay
S$334
20 Sept - 21 Sept
includes taxes & fees
Sofitel Philadelphia at Rittenhouse Square
See all 3,087 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.

Frequently asked questions

How much does a Chestnut Hill holiday 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 holiday.
Where should I stay in Chestnut Hill?
Most who travel to Chestnut Hill include Liberty Bell Centre 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 holiday?
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 holiday 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 favourite 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.
Can I choose my airline with a Chestnut Hill Expedia holiday package?
Yes — that's the beauty of an Expedia holiday 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 holiday 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 holiday 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)
Rare and ancient plant species can be admired in their thousands at this spectacular outdoor attraction.
See properties

Woodmere Art Museum

You can browse the exhibits at Woodmere Art Museum, a museum with a storied past, during your travels to Philadelphia. Discover the top-notch restaurants and acclaimed art galleries in this vibrant area.
See properties

Hipster Home

Enjoy an outing to Hipster Home during your stay in Philadelphia. Discover the fascinating museums and shops in this vibrant area.
See properties

The Stagecrafters Theater

Enjoy a show at The Stagecrafters Theater, a theatre with a story to tell in Philadelphia. Experience the fascinating museums and acclaimed art galleries in this vibrant area.
See properties

Things to do

LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

S$32
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

S$75
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

S$62
per adult
94% 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.