Chestnut Hill vacation rentals

We found 8 vacation rentals — enter your dates for availability

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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Find out more about Chestnut Hill

Find out more about Chestnut Hill

Why visit Chestnut Hill

  1. Charming cobblestone streets: Wander through picturesque pathways that provide a quaint atmosphere perfect for leisurely strolls.
  2. Cultural experiences: Explore modern and historic colleges, art museums, and vibrant local art scenes catering to diverse interests.
  3. Family-friendly activities: Chestnut Hill offers a variety of outdoor adventures suitable for visitors of all ages.
  4. Welcoming community: Experience the warm hospitality of friendly locals while uncovering hidden gems within the neighbourhood.
  5. Comfortable accommodations: Choose from a range of vacation rentals, including cozy cottages and modern apartments for a memorable stay.

Popular types of accommodation around Chestnut Hill

Planning a getaway to Chestnut Hill? You're in for a treat! This charming neighbourhood offers a range of vacation rentals, including houses, cozy cottages, and modern apartments. Whether you're searching for Chestnut Hill apartments or Philadelphia Chestnut Hill rentals, you’ll find the perfect spot to unwind and explore. Discover the best accommodations in Chestnut Hill that promise comfort, convenience, and a memorable stay!

  • Houses: The top choice for visitors in Chestnut Hill, offering spacious and comfortable accommodations perfect for families or groups.
  • Apartments: A popular option for those seeking a home-like atmosphere, ideal for longer stays or couples.
  • Cottages: Charming and cozy, these rentals provide a quaint escape in a picturesque setting.
  • Condos: Convenient and modern, condos offer amenities and a great location for exploring the area.
  • Cabins: A delightful choice for nature lovers, cabins provide a rustic experience close to the outdoors.**

Top attractions around Chestnut Hill

Chestnut Hill, Philadelphia, offers a delightful blend of family-friendly, outdoor, and city-themed activities. Visitors can explore a variety of attractions, including modern and historic colleges and universities, as well as art museums. This charming area caters to those seeking cultural experiences, making it an ideal destination for families and travellers looking to immerse themselves in the local scene.

  1. Pennsylvania Convention Center: A hub for events and conferences, this venue exudes a professional atmosphere. It's an architectural marvel that hosts various gatherings, making it a great spot to experience the vibrant business culture of Philadelphia.
  2. University of Pennsylvania: This prestigious institution combines modern architecture with rich history. Stroll through the campus to feel the energetic city vibe, and explore its innovative programs and beautiful green spaces.
  3. Philadelphia Museum of Art: Renowned for its vast collection, this museum offers a deep dive into art and culture. Don't forget to run up the iconic steps and enjoy stunning views of the city skyline.

Things to do recommended for couples

For a memorable couple's getaway in Chestnut Hill, catch a captivating concert at the Academy of Music, explore the scenic charm of Boathouse Row with its outdoor adventures, or enjoy the rhythm of romance at a Philadanco dance performance. Each experience promises unforgettable moments together.

Things to do recommended for families

Your family will love exploring Fairmount Park, perfect for relaxation, just 9.7km from Chestnut Hill. For sports enthusiasts, Tom Gola Arena offers exciting events 6.4km away. Don't miss Francisville Playground, a delightful family-friendly outdoor space located 12.9km from your base.

Things to do recommended for groups

Group travelers to Chestnut Hill can enjoy a performance at the Mann Center for the Performing Arts, shop at the King of Prussia Mall, and savour local delicacies at the Reading Terminal Market, all while soaking in the vibrant local culture and atmosphere of Philadelphia.

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

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Chestnut Hill with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Chestnut Hill with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your location in relation to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to Chestnut Hill: For many, a family vacation wouldn’t be the same without their furry companion. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chestnut Hill: If you’re seeking vacation rentals with special offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Chestnut Hill

Chestnut Hill, Philadelphia, is a charming neighbourhood perfect for family-friendly adventures and outdoor exploration. Wander through its picturesque cobblestone streets, enjoy a relaxed atmosphere, and discover the vibrant local art scene. Nearby areas offer a blend of urban energy and quiet residential charm, making it an ideal base for exploring both the lively city and serene surroundings. Experience the warm hospitality of friendly locals as you uncover the hidden gems of this delightful community.

  • Wyndmoor: Located a mere 966m from Chestnut Hill, Wyndmoor is a charming neighbourhood that offers a family-friendly atmosphere combined with urban convenience. Visitors can enjoy a variety of educational and recreational spaces, making it an ideal spot for families and business travellers alike. Notable highlights include a modern college university and a historic college, both of which contribute to the area's vibrant educational landscape. Additionally, residents and guests can explore local parks and a shopping centre, ensuring a well-rounded experience.
  • Center City: Situated approximately 14.5km from Chestnut Hill, Center City is the bustling core of Philadelphia, attracting families and business visitors with its diverse offerings. Known for its vibrant arts scene, the neighbourhood boasts a state-of-the-art arts centre and numerous shopping areas. Key attractions include an event conference venue and a convention centre, making it a hotspot for both leisure and corporate activities. Sports enthusiasts will appreciate the nearby stadium, which often hosts major events and games.
  • Flourtown: Just 3.2km from Chestnut Hill, Flourtown is a quaint city perfect for outdoor enthusiasts and families. The area is rich in educational opportunities and features a variety of shopping centres and malls for a delightful retail experience. Noteworthy attractions include both a historic and a modern college university, alongside a serene lake ideal for leisurely strolls or picnics. Flourtown's blend of outdoor activities and vibrant local culture makes it a must-visit destination during your stay.

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January33.3°F (0.7°C)Light RainMostly SunnySlightly LowSlightly Low
February35.4°F (1.9°C)Light RainMostly SunnyAverageSlightly Low
March43.0°F (6.1°C)Light RainMostly SunnyAverageSlightly Low
April53.6°F (12.0°C)Light RainMostly SunnyAverageAverage
May63.5°F (17.5°C)Light RainMostly SunnySlightly LowSlightly High
June72.1°F (22.3°C)Light RainMostly SunnyAverageSlightly High
July78.3°F (25.7°C)Light RainMostly SunnyAverageSlightly High
August76.3°F (24.6°C)Light RainMostly SunnySlightly LowAverage
September69.8°F (21.0°C)Light RainMostly SunnySlightly HighAverage
October58.8°F (14.9°C)Light RainMostly SunnyAverageAverage
November46.9°F (8.3°C)Light RainMostly SunnySlightly HighAverage
December39.4°F (4.1°C)Light RainMostly SunnySlightly HighAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to utilise our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your travel needs!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for planning your travels, allowing you to create new trips, resume your previous plans, or manage your itinerary with ease. Here, you can easily access the properties you've saved or booked, organized into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chestnut Hill?
The most desirable types of vacation rentals in Chestnut Hill are apartments. Hoping for something different? Vrbo has many options to match our guests' unique requirements, so you'll see vacation homes in all sizes and shapes. The perfect fit is waiting for you — discover yours today.
How much does it cost to rent a vacation rental in Chestnut Hill?
Several things can affect the price of a vacation rental in Chestnut Hill, including the type of property, season and length of stay. Still, all of our vacation homes have something in common — excellent value. Just add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Chestnut Hill?
Prices for beach houses in Chestnut Hill differ depending on the size and style of the property and when you plan to travel. Just enter your travel dates into Vrbo and how many guests to see your rental options and prices. From there you can use our filter tool to refine your search by ratings, amenities, nearby activities and more.
Are there pet-friendly vacation rentals in Chestnut Hill?
With five properties that allow pets, your little buddy can join in on your Chestnut Hill break. Use our filter tool to search our pet-friendly vacation rentals and find a stay that's pawfect on Vrbo.
What are popular rental amenities in Chestnut Hill?
A garden, nearby museums and a barbecue grill are rated the most popular rental amenities in Chestnut Hill. Whether you're taking to the road as a party of one, with your better half or a group of family members, Vrbo can help you find a vacation home that suits your style with all the options you need.
Are there large group vacation rentals in Chestnut Hill?
With two Chestnut Hill vacation homes that can accommodate five or more people, you can bring a few extra family members or buddies along. Whether you're planning an informal gathering or a birthday party, we'll help you book a comfortable space to fit the occasion.
Are there vacation rentals in Chestnut Hill that welcome kids?
Gather your whole crew for a memorable adventure in Chestnut Hill at one of our five family-friendly vacation rentals. These stays provide conveniences that are great for getaways with children, including dining rooms, bunk beds and outdoor spaces. Simply click on the "Properties good for families" filter and choose your favorite.
What are the top attractions for families in Chestnut Hill?
Keeping the kiddos entertained during your Chestnut Hill vacation is simple with these fabulous family-friendly attractions:

  • Philadelphia Zoo
  • The Franklin Institute
  • Rocky Steps

Can I find two-bedroom vacation rentals in Chestnut Hill?
Pick from three two-bedroom properties in Chestnut Hill. Put the kids in the second room or fill it with a couple of your besties. There's ample space for whoever's fortunate enough to be joining your adventure.
Are there vacation rentals with WiFi in Chestnut Hill?
Take your pick of two vacation rentals with WiFi in Chestnut Hill. If you'd like to disconnect from the world on your trip, but still need to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Chestnut Hill?
Chestnut Hill has four vacation rentals where you'll be able to spend your days in air-conditioned comfort. To book a property on Vrbo that has this perk, enter your dates of travel and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Chestnut Hill?
The minimum required age is normally 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your chosen Chestnut Hill vacation rental before making a booking.
How long can I rent a vacation rental in Chestnut Hill for?
The amount of time you can book a Chestnut Hill vacation home for depends on the property. Simply enter your preferred travel dates to view options offering extended stays. They include everything you need to make your extended break more comfortable and enjoyable, such as kitchens and laundries. Some Vrbo vacation rentals may also offer weekly or monthly discounts, so you can stay longer for less money.

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