Vacation Homes in Chestnut Hill, Philadelphia: House Rentals & More

Scroll through and select from vacation rentals in Chestnut Hill to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a garden and pool. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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Condo/Apartment

Find properties near top attractions in Chestnut Hill

Morris Arboretum

Find the best place to stay - Chestnut Hill

Showing deals for: Oct 17 - Oct 20

Whether you're an Amazon Prime subscriber or a Netflix enthusiast, simply log in to your account and enjoy a relaxing evening indoors. With the 65-inch Smart TV, your favorite show or movie is just a few clicks away

No-stairs - Chestnut Hill 2 BR/2 Bath

Sleeps 4 · 2 bedrooms · 2 bathrooms

Fees included upfront

Impeccably Restored and Appointed Row-house

Sleeps 6 · 3 bedrooms · 2 bathrooms

Fees included upfront

Enjoy the convenience of a fully-equipped kitchen

Patio/ Grill / Chestnut Hill / 2 BR/ 1.5 BA

Sleeps 4 · 2 bedrooms · 1+ bathroom

Fees included upfront

Whether you're an Amazon Prime subscriber or a Netflix enthusiast, simply log in to your account and enjoy a relaxing evening indoors. With the 55-inch Smart TV, your favorite show or movie is just a few clicks away

Cheerful Chestnut Hill 2 BR/1.5 BA/Private Deck

Sleeps 4 · 2 bedrooms · 1+ bathroom

Fees included upfront

Charming 2-bedroom apartment w/ WiFi, AC in phenomenal Germantown, Philadelphia

Sleeps 4 · 2 bedrooms · 1 bathroom

Fees included upfront

Top rated rentals - Chestnut Hill

Philadelphia Vacation Rental | 3BR | 2BA | 1,590 Sq Ft | 4 Steps Required

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Enjoy full kitchens, laundry, pools, yards and more
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We stand for diversity, inclusion and families everywhere.
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Find out more about Chestnut Hill

Why visit Chestnut Hill

Family-Friendly Activities: Enjoy a range of attractions that cater to all ages, ensuring fun for the whole family.
Outdoor Adventures: Explore beautiful parks and nature trails that offer plenty of opportunities for hiking and picnicking.
Cultural Experiences: Visit modern colleges, universities, and historical museums to immerse yourself in local culture.
Charming Neighborhood: Stroll through picturesque streets filled with local cafes, shops, and a friendly atmosphere.
Diverse Accommodations: Choose from cozy apartments and charming houses that provide a perfect home base for exploration.

Popular types of accommodation around Chestnut Hill

Planning a getaway to Chestnut Hill? You're in for a treat! This charming neighborhood offers a variety of vacation rentals, including cozy apartments, inviting apart hotels, and spacious private homes. Whether you’re searching for Chestnut Hill apartments, township apartments, or houses for rent, you’ll find plenty of options to suit your needs. Enjoy the convenience of staying in Philadelphia while experiencing the unique charm of Chestnut Hill!

Apartments: The top choice for travelers in Chestnut Hill, offering convenient amenities and a home-like atmosphere.
Houses: A popular option for groups or families seeking privacy and space during their stay.
Condos: A great alternative for those wanting modern comforts and access to community facilities.
Cottages: Ideal for a quaint and cozy experience, perfect for a romantic getaway or peaceful retreat.
Villas: Luxurious accommodations that provide ample space and upscale features for a lavish vacation.**

Top attractions around Chestnut Hill

Chestnut Hill, Philadelphia, offers a perfect blend of family-friendly activities, outdoor adventures, and urban exploration. Visitors can immerse themselves in local culture by exploring modern colleges and universities, as well as historical museums. With a variety of attractions catering to those seeking a rich cultural experience and family outings, Chestnut Hill is an ideal destination for anyone looking to enjoy a memorable vacation.

Pennsylvania Convention Center: Located 9 miles from Chestnut Hill, this bustling venue hosts various events and conferences, offering a dynamic atmosphere filled with business energy and networking opportunities.
Philadelphia Museum of Art: Situated 8 miles away, this iconic museum boasts an extensive collection of art, showcasing diverse cultures and historical pieces, making it a cultural treasure in the city.
Rittenhouse Square: Just 9 miles from Chestnut Hill, this vibrant neighborhood features a beautiful park surrounded by shops and restaurants, providing a lively urban experience perfect for relaxation and people-watching.

Things to do recommended for couples

Experience a romantic getaway in Chestnut Hill! Enjoy a captivating concert at the Kimmel Center, paddle along the scenic Boathouse Row, or indulge in luxury at the Merchantville Country Club. Each venue offers a unique vibe perfect for couples seeking adventure and elegance.

Things to do recommended for families

Your family will enjoy the thrilling adventure at Speed Raceway, the relaxing atmosphere of Fairmount Park, and the exciting sports vibes at Lincoln Financial Field, all within a short drive from Chestnut Hill. These experiences promise fun and memorable moments for everyone!

Things to do recommended for groups

Groups visiting Chestnut Hill can savor local flavors at the Reading Terminal Market, shop at King of Prussia Mall for an entertaining experience, and enjoy a cultural performance at the Mann Center for the Performing Arts. Each destination offers a unique vibe for memorable group outings.

What do I need to keep in mind when booking a vacation around Chestnut Hill

If you're planning a trip with a group, family, or pets, or if you’re considering an extended stay, be sure to prioritize your search accordingly. Here are some helpful Vrbo booking tips to assist you.

Traveling to Chestnut Hill with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor space for group activities. Luckily, you can easily filter for these options and many more on Vrbo.
Traveling to Chestnut Hill with young kids: Traveling with young kids can be a bit tough. It's important to prioritize their comfort and safety, along with having suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
Taking your pets with you to Chestnut Hill: For many families, a vacation isn't truly fulfilling without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
Planning for a long term stay visiting Chestnut Hill: If you're searching for vacation rentals with discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Chestnut Hill

Chestnut Hill offers a delightful mix of family-friendly activities and urban charm, making it an ideal base for exploration. Just a short drive away, downtown Philadelphia boasts rich history and vibrant neighborhoods, each with its own unique vibe. Wander through picturesque streets, enjoy local cafes, and immerse yourself in the friendly atmosphere. Whether you're seeking outdoor adventures or cultural experiences, Chestnut Hill and its surroundings promise a memorable vacation filled with discovery.

Wyndmoor: Located a short 0.6 miles from Chestnut Hill, Wyndmoor is a charming neighborhood known for its family-friendly atmosphere and outdoor experiences. Visitors enjoy exploring its parks and recreational areas, which provide ample opportunities for activities like hiking and picnicking. The local shopping center offers a delightful mix of boutiques and eateries, while the nearby historic college and art museum add cultural richness to your visit. Wyndmoor is perfect for those seeking a blend of education, leisure, and community vibes.
Flourtown: Situated 2 miles from Chestnut Hill, Flourtown is a vibrant city that caters to families and outdoor enthusiasts alike. The area is well-known for its outdoor recreational facilities, including beautiful parks and a scenic lake that invites activities such as walking, jogging, or simply relaxing by the water. Flourtown's shopping mall and various educational venues make it a great destination for those looking to shop and learn. With its historical college university as a local landmark, Flourtown offers a unique blend of history and modern amenities.
East Mount Airy: Just 2 miles from Chestnut Hill, East Mount Airy is a lively neighborhood that combines city life with outdoor fun. Visitors can enjoy the gaming excitement at local casinos or unwind at nearby resorts and golf courses. The area features several parks that provide green spaces for relaxation and outdoor activities. East Mount Airy is also home to a prominent event conference venue, making it an appealing choice for travelers interested in both leisure and business opportunities.

Best time to go to Chestnut Hill

If you're planning a trip to Chestnut Hill, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in September and November to December, while off-peak times, like January, May and August tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	33.3°F (0.7°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	35.4°F (1.9°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	43.0°F (6.1°C)	Light Rain	Mostly Sunny	Average	Average
April	53.6°F (12.0°C)	Light Rain	Mostly Sunny	Average	Slightly High
May	63.5°F (17.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High
June	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	78.3°F (25.7°C)	Light Rain	Mostly Sunny	Average	Average
August	76.3°F (24.6°C)	Light Rain	Mostly Sunny	Slightly Low	Average
September	69.8°F (21.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
October	58.8°F (14.9°C)	Light Rain	Mostly Sunny	Average	Average
November	46.9°F (8.3°C)	Light Rain	Mostly Sunny	Slightly High	Average
December	39.4°F (4.1°C)	Light Rain	Mostly Sunny	Slightly High	Average

Booking with Vrbo is simple

Are you aiming to get the best deal on your upcoming journey? One effective strategy is to remain flexible with your travel dates, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. When searching for the ideal Vrbo property that suits your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit!

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you’ll earn OneKeyCash™ on the full booking amount. It truly benefits you to be the planner! Become a part of our OneKey rewards program to unlock exclusive member discounts and accumulate OneKeyCash™ on qualifying stays. Sign up today and begin earning!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your ongoing travel arrangements, and keep track of your bookings. Your saved or confirmed properties are categorized into Potential, Upcoming, or Current Trips for easy access. To start exploring your Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Frequently asked questions

How much does it cost to rent a vacation home in Chestnut Hill?

Prices for vacation rentals in Chestnut Hill vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chestnut Hill to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.

Are there any discounts for Chestnut Hill vacation house rentals?

You can find great discounts on house rentals in Chestnut Hill on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Are there any Chestnut Hill vacation rentals with parking?

Vrbo offers a wide selection of vacation rentals in Chestnut Hill with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

Can I find long-stay vacation rentals in Chestnut Hill?

A long-stay vacation rental in Chestnut Hill is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

When is the best time to visit Chestnut Hill for a vacation rental?

December is the most popular time to visit Chestnut Hill, where the charm of the holiday season transforms the neighborhood into a winter wonderland. From October through December, the peak season attracts travelers eager to experience festive decorations, local markets, and seasonal events that showcase the community's warm spirit. The crisp air, with temperatures ranging from the low 30s to mid-50s Fahrenheit, creates a cozy atmosphere superb for leisurely strolls and outdoor gatherings.

During these months, visitors can take part in the vibrant local culture by exploring the quaint shops along Germantown Avenue, where unique gifts and artisanal products abound. The picturesque parks, adorned with falling leaves in the autumn and twinkling lights in the winter, provide an inviting backdrop for outdoor activities and sightseeing.

For those seeking a more budget-friendly experience, May offers a wonderful opportunity to visit Chestnut Hill. This month sees fewer tourists but still presents beautiful spring blooms and a tranquil ambiance, ideal for enjoying the area's parks and gardens. The pleasant weather allows for comfortable outdoor activities, making it a great time for leisurely picnics or nature walks.

Ultimately, your choice of when to visit Chestnut Hill will hinge on whether you prefer the lively holiday atmosphere of peak season or the serenity and beauty of springtime.

How early should I book a Chestnut Hill vacation rental?

Book your Chestnut Hill vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

What are the top attractions in Chestnut Hill?

In Chestnut Hill, visitors can enjoy a charming blend of nature and culture. The neighborhood is known for its beautiful gardens and parks, such as the Morris Arboretum, which features an extensive collection of trees, shrubs, and picturesque walking paths. For shopping and dining, the quaint Germantown Avenue is lined with boutique shops, cafes, and restaurants, making it a vibrant area to explore. Additionally, the nearby Chestnut Hill College adds a touch of academic charm to the area, and the historic architecture throughout the neighborhood contributes to its unique character.

Can I change or cancel my Chestnut Hill home rental booking on Vrbo?

To find Chestnut Hill vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.