Chestnut Hill Vacations from $208

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Your Chestnut Hill Vacation

Whatever your style of travel, you can discover it all with a tailor-made Chestnut Hill vacation package. Spend your next getaway enjoying this neighborhood's gift and craft shops and all the rest of its charms. Begin your trip to Chestnut Hill by heading to nearby attractions such as Arcadia University, Morris Arboretum and Morris Arboretum. Whatever your travel goals or budget, booking your ideal Chestnut Hill vacation is simple with Expedia.

The Latest Chestnut Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Trolley Stop Motel

Trolley Stop Motel

Save 100% on your flight
$208
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
7.8/10 Good! (829 reviews)
Really nice staff comfortable room. Bathroom was a little small but not a big deal for me. Very reasonable price. Will stay there again

Reviewed on Oct 18, 2026

Casa De Miliki

Casa De Miliki

South Philadelphia
$3,636
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
No reviews
Orchard Way

Orchard Way

Save 100% on your flight
$2,010
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
No reviews
New Season Royals

New Season Royals

Save 100% on your flight
$290
per person
Dec 3 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
9.2/10 Wonderful! (156 reviews)
Tudor Place

Tudor Place

Save 100% on your flight
$2,757
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
No 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
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 Liberty Place, and hop on the metro to see more the city at 15th-16th & Locust Station or 19th St Station.

Find hotels in Rittenhouse Square
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

Discover history at Independence National Historical Park, stroll along the 3rd Street Corridor for galleries and boutiques, and enjoy vibrant nightlife with quality restaurants and bars. Don't miss the monthly First Friday event for art and design showcases.

Find hotels in Old City
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

Home to prestigious universities like Penn and Drexel, this vibrant area offers cultural experiences at the Penn Museum and Institute of Contemporary Art. Enjoy shopping at the 40th Street retail corridor and easy access to various transportation options.

Find hotels in University City
A historic waterfront with classical architecture, including a neoclassical building and a bridge.

West Philadelphia

1 out of top 10 points of interest in this area

Home to universities like University of Pennsylvania and Drexel, this area boasts cultural venues such as Mann Music Center and Bushfire Theater. Explore Lancaster Avenue's shops and restaurants, or visit the historic Philadelphia Zoo.

Find hotels in West Philadelphia

Chestnut Hill Hotel Deals

Club Quarters Hotel Rittenhouse Square, Philadelphia

Club Quarters Hotel Rittenhouse Square, Philadelphia

1628 Chestnut St Philadelphia PA
Fully refundableReserve now, pay when you stay
$118 nightly
$137 total
Oct 29 - Oct 30
Total with taxes and fees
Club Quarters Hotel Rittenhouse Square, Philadelphia
Doubletree by Hilton Philadelphia Airport

Doubletree by Hilton Philadelphia Airport

4509 Island Ave Philadelphia PA
Fully refundableReserve now, pay when you stay
$106 nightly
$123 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (194 reviews)
"Everything is decent and in order"

Reviewed on Oct 23, 2026

Doubletree by Hilton Philadelphia Airport
Motto by Hilton Philadelphia Rittenhouse Square

Motto by Hilton Philadelphia Rittenhouse Square

31 S 19th St Philadelphia PA
Fully refundableReserve now, pay when you stay
$81 nightly
$94 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (2,570 reviews)
"Terrific restaurant"

Reviewed on Oct 23, 2026

Motto by Hilton Philadelphia Rittenhouse Square
See all 3,088 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.
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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

Woodmere Art Museum

You can browse the exhibits at Woodmere Art Museum, a museum with a story of its own, during your travels to Philadelphia. Discover the top-notch restaurants and acclaimed art scene in this vibrant area.
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Hipster Home

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

Enjoy a show at The Stagecrafters Theater, a storied theater in Philadelphia. Experience the fascinating museums and acclaimed art scene in this vibrant area.
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Things to do

LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

$25
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
Polaris Slingshot Rental-Philadelphia, PA

Polaris Slingshot Rental-Philadelphia, PA

$250
per traveler
Polaris Slingshot Rental-Philadelphia, PA
BYOB Historically Hilarious Trolley Tour of Philadelphia

BYOB Historically Hilarious Trolley Tour of Philadelphia

$49
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.