Chestnut Hill holiday lettings

We found 7 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Chestnut Hill to find one that's perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Chestnut Hill

  • Charming architecture: Stroll through picturesque streets adorned with historic homes and quaint shops.
  • Cultural experiences: Explore modern and historic universities, along with captivating art museums.
  • Outdoor activities: Enjoy the lush greenery of Fairmount Park, perfect for leisurely walks and picnics.
  • Family-friendly environment: Discover a vibrant community that offers enjoyable activities for all ages.
  • Diverse accommodation options: Choose from private homes to stylish apartments to suit every preference and budget.

Popular types of accommodation around Chestnut Hill

If you're planning a getaway to Chestnut Hill, the next exciting step is selecting your accommodation. From houses to charming cottages and stylish apartments, there’s something to suit every taste and budget. Explore our selection of house rentals and luxury apartments in Chestnut Hill to find the perfect base for your adventure.

  • Houses: The top choice for visitors to Chestnut Hill, offering spacious and comfortable stays ideal for families, groups, or couples.
  • Flats: A popular option for those seeking a convenient and modern place to stay while exploring the area.
  • Cottages: Charming and cozy accommodations that provide a quaint retreat amidst the lovely surroundings.
  • Condos: Stylish and well-equipped living spaces perfect for short or extended stays.
  • Villas: Luxurious residences that offer an upscale experience with plenty of room to relax.**

Top attractions near Chestnut Hill

Chestnut Hill offers a delightful blend of family-friendly activities, urban charm, and outdoor excursions. Visitors can explore a mix of modern and historic universities, as well as captivating art museums. This vibrant area caters to those seeking cultural experiences, making it an ideal destination for families and city enthusiasts alike. Enjoy the rich offerings and create unforgettable memories in this picturesque Philadelphia neighbourhood.

  • University of Pennsylvania: A prestigious modern university renowned for its vibrant campus atmosphere, where historic architecture meets contemporary learning. Explore its beautiful gardens and dynamic student life.
  • Pennsylvania Convention Center: A bustling event space that hosts a variety of conferences and exhibitions. Experience the business vibes and the networking opportunities amidst its impressive facilities.
  • Philadelphia Museum of Art: An iconic cultural landmark housing an extensive collection of art. Enjoy its impressive galleries and the famous Rocky Steps, offering a blend of history and creativity.

Things to do recommended for couples

For a romantic getaway in Chestnut Hill, enjoy an enchanting evening at the Academy of Music, just 5.6km away, or embrace adventure at Boathouse Row, 5.0km distant. Don't miss Philadanco for a captivating dance experience, also 5.0km away, blending romance with culture.

Things to do recommended for families

Families in Chestnut Hill can enjoy a day of relaxation at Fairmount Park, just 3.7km away, or cheer on their favourite teams at Tom Gola Arena, 2.5km away. For outdoor fun, Francisville Playground, 5.0km distant, offers a vibrant atmosphere for children to play.

Things to do recommended for groups

Groups visiting Chestnut Hill can enjoy the vibrant atmosphere at Reading Terminal Market, indulge in shopping and entertainment at King of Prussia Mall, and experience cultural performances at the Mann Center for the Performing Arts, all within a short distance from the area.

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

If you’re travelling with a group, family, pets, or planning an extended stay, be sure to select the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Chestnut Hill with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Chestnut Hill with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with 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 holiday wouldn't feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most 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 in search of holiday rentals with discounts for month-long stays or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Chestnut Hill

Chestnut Hill, a charming neighbourhood in Philadelphia, offers a delightful mix of urban and family-friendly vibes. Explore the picturesque streets lined with historic homes and local shops, perfect for leisurely strolls. Nearby attractions include the lush greens of Fairmount Park and the vibrant atmosphere of local cafés. With its friendly community and rich history, Chestnut Hill provides an ideal backdrop for a memorable holiday experience.

  • Philadelphia: Philadelphia, a vibrant metropolis located 5.6km from Chestnut Hill, is rich in history and culture. Visitors flock to this city for a family-friendly atmosphere, urban experiences, and outdoor adventures. Explore renowned attractions such as the Liberty Bell and Independence Hall, or indulge in retail therapy at local shopping districts. The city is also home to a thriving arts scene, with museums and galleries that cater to all tastes. Don't miss the sports facilities, where you can catch a game at one of the famous stadiums, making Philadelphia a perfect blend of history, sport, and entertainment.
  • Wyndmoor: Just 373m from Chestnut Hill, Wyndmoor is a charming neighbourhood that offers a delightful blend of family-oriented activities and business facilities. This peaceful area features a variety of educational institutions and recreational spaces, ideal for both relaxation and learning. Visitors can enjoy the local parks and art museums, which showcase the community's creative spirit. Wyndmoor's proximity to Chestnut Hill makes it a convenient stop for those wanting to explore more while still enjoying a quieter atmosphere in a lovely suburban setting.
  • Flourtown: Located 1.2km from Chestnut Hill, Flourtown is a picturesque city that invites visitors with its family-friendly vibe and outdoor pursuits. This area boasts excellent shopping centres and malls, perfect for a day of retail exploration. With attractions such as historic colleges and serene lakes, Flourtown offers a unique blend of heritage and natural beauty. Enjoy leisurely strolls by the water or indulge in local dining, making Flourtown a delightful addition to your itinerary, whether for business or pleasure.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 SunnyAverageAverage
July78.3°F (25.7°C)Light RainMostly SunnyAverageSlightly High
August76.3°F (24.6°C)Light RainMostly SunnySlightly LowSlightly High
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 a breeze

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly environment for planning your holidays, allowing you to easily start new trips, resume your previous ones, or manage your travel arrangements. You can conveniently find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring the features of Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Chestnut Hill?
The most desirable types of holiday rentals in Chestnut Hill are apartments. Hoping for something different? Vrbo has many options to match our guests' unique requirements, so you'll see holiday homes in all sizes and shapes. The perfect fit is waiting for you — discover yours today.
How much does it cost to rent a holiday rental in Chestnut Hill?
Several things can affect the price of a holiday rental in Chestnut Hill, including the type of property, season and length of stay. Still, all of our holiday 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 holiday 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 holiday 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 holiday home that suits your style with all the options you need.
Are there large group holiday rentals in Chestnut Hill?
With two Chestnut Hill holiday 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 holiday 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 holiday 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 favourite.
What are the top attractions for families in Chestnut Hill?
Keeping the kiddos entertained during your Chestnut Hill holiday is simple with these fabulous family-friendly attractions:

  • Philadelphia Zoo
  • The Franklin Institute
  • Rocky Steps

Can I find two-bedroom holiday 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 holiday rentals with WiFi in Chestnut Hill?
Take your pick of two holiday 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 holiday rentals with air conditioning in Chestnut Hill?
Chestnut Hill has four holiday 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 holiday 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 holiday rental before making a booking.
How long can I rent a holiday rental in Chestnut Hill for?
The amount of time you can book a Chestnut Hill holiday 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 holiday rentals may also offer weekly or monthly discounts, so you can stay longer for less money.

More Holiday Rentals ideas

People also search for