Chester vacation rentals

We found 277 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Chester that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the best amenities for spending time at your vacation home, which might include WiFi and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

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Find out more about Chester

Why visit Chester

  • Urban Parks: Enjoy the green spaces and recreational activities in Chester's urban parks, perfect for family outings.
  • Cultural Experiences: Discover local history and culture through attractions and vibrant neighborhoods that showcase Chester's charm.
  • Family-Friendly Activities: Engage in various activities that cater to families, ensuring fun for all ages during your visit.
  • Sporting Opportunities: Take advantage of nearby sports venues and events for an exciting experience.
  • Diverse Accommodations: Choose from a range of vacation rentals, from cozy cottages to spacious homes, for a comfortable stay.

Popular types of accommodation in Chester

Discover the perfect getaway in Chester with Vrbo's diverse vacation rentals. Whether you're seeking spacious houses, cozy apartments, or charming cottages, we have options for every traveler. Ideal for families or groups, our house rentals offer ample bedrooms and shared facilities for a comfortable stay. Start your search for the ideal cottage or house rental in Chester and enjoy a memorable vacation experience.

  • Houses: The top choice for visitors in Chester, these homes offer a comfortable and spacious environment, perfect for families or groups.
  • Apartments: A popular option for couples or solo travelers, apartments provide a cozy and convenient stay in Chester.
  • Cottages: Charming and quaint, cottages offer a unique retreat experience for those looking to relax in Chester.
  • Condos: Ideal for those seeking modern amenities, condos combine comfort and style for a pleasant stay.
  • Cabins: A favorite for nature lovers, cabins provide a rustic escape close to Chester's scenic areas.**

Top attractions near Chester

Chester, Pennsylvania, is a fantastic destination for families and sports enthusiasts alike, offering a blend of cultural and urban experiences. Visitors can explore local attractions such as modern colleges and universities, urban parks, and charming neighborhoods. Whether you're seeking a vibrant city atmosphere or family-friendly activities, Chester has something for everyone to enjoy during their vacation.

  • Wells Fargo Center: Located 10 miles from Chester, this vibrant arena is a hub for sports and entertainment, hosting thrilling events from basketball to concerts, creating an electrifying atmosphere for families and fans alike.
  • University of Pennsylvania: Situated 11 miles away, this prestigious modern university boasts beautiful architecture and a dynamic campus life, offering a glimpse into academic excellence and cultural diversity in an urban setting.
  • Rittenhouse Square: Just 12 miles from Chester, this charming neighborhood features a picturesque park surrounded by upscale shops and cafes, perfect for a leisurely stroll or enjoying a meal outdoors in a vibrant city vibe.

Things to do recommended for couples

Ready for a romantic getaway in Chester? Visit Grace Winery for a lovely atmosphere, or enjoy a thrilling day at Boathouse Row. Don't miss Auburn Road Vineyard for wine tasting and entertainment—perfect for couples looking to create unforgettable memories together.

Things to do recommended for families

Your family vacation in Chester, Pennsylvania, offers exciting experiences like cheering at Lincoln Financial Field, skating at Ice Works Skating Complex, and relaxing at Daskalakis Athletic Center. Enjoy sports, adventure, and wellness in a vibrant atmosphere perfect for family fun.

Things to do recommended for groups

Explore the vibrant Reading Terminal Market for local eats, enjoy a show at the Mann Center for the Performing Arts for a cultural night out, or experience adrenaline at Bridgeport Speedway for thrilling motor racing. Perfect activities for group travelers looking to immerse themselves in Chester.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chester

If you're traveling with a group, family, or pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chester with a group: Think about how many bedrooms you'll require, as well as any amenities you'd like, such as a full kitchen or outdoor space for gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Chester with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chester: For many families, a vacation wouldn't be the same without their furry companion. If you can relate, take a look at Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chester: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rental options. Don't forget to include features like a parking spot, a well-equipped kitchen, or a private pool in your search to enhance your experience.

Where to stay in Chester

Chester, Pennsylvania offers a delightful blend of family-friendly activities and urban charm, making it a perfect vacation spot. Explore its vibrant neighborhoods, where friendly locals create a warm atmosphere. Enjoy fun attractions in the city center and discover the historical significance of the area. Nearby regions provide additional opportunities for sports and relaxation, ensuring a memorable experience for every traveler looking to embrace the unique vibes of Chester.

  • Philadelphia: As a bustling metropolis, Philadelphia offers a rich tapestry of history, culture, and entertainment. Located in close proximity to Chester, it is a prime destination for families and outdoor enthusiasts alike. Visitors can explore world-class museums, enjoy shopping in vibrant districts, and catch a game at the iconic sports facilities. Landmarks such as the Liberty Bell and the Philadelphia Museum of Art provide a historical backdrop, while modern attractions like the Wells Fargo Center keep the energy high. Whether you're indulging in famous cheesesteaks or strolling through Fairmount Park, Philadelphia promises an unforgettable urban experience.
  • Eddystone: This charming village, located just 1 mile from Chester, is perfect for families seeking a blend of sports and city life. Eddystone boasts a welcoming atmosphere with easy access to educational venues and local arts centers. Families can also enjoy the nearby amusement park, making it an ideal spot for a fun-filled day. The local stadium and sports facilities host various events, ensuring there's always something exciting happening. With its proximity to Chester, Eddystone serves as a peaceful retreat while still offering the conveniences of urban living.
  • Upland: Situated a mile away from Chester, Upland is a quaint village that caters to families and business travelers alike. This community is known for its vibrant arts scene, shopping center, and local theater, making it a delightful place to explore. Visitors can enjoy the convention center for business events or relax at the local park for a leisurely day out. Upland’s close-knit environment and easy access to Chester's attractions provide a perfect balance of tranquility and excitement, making it an appealing destination for a variety of travelers.

Best time to go to Chester

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January33.3°F (0.7°C)Light RainMostly SunnySlightly LowSlightly Low
February35.6°F (2.0°C)Light RainMostly SunnyAverageSlightly Low
March43.0°F (6.1°C)Light RainMostly SunnyAverageSlightly Low
April53.8°F (12.1°C)Light RainMostly SunnySlightly HighAverage
May63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly High
June72.1°F (22.3°C)Light RainMostly SunnySlightly HighAverage
July78.1°F (25.6°C)Light RainMostly SunnySlightly HighAverage
August76.1°F (24.5°C)Light RainMostly SunnyAverageSlightly High
September69.6°F (20.9°C)Light RainMostly SunnyAverageAverage
October58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
November46.8°F (8.2°C)Light RainMostly SunnySlightly LowSlightly High
December39.2°F (4.0°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers an easy-to-use platform for planning your travel. You can start new trips, continue from where you paused, or check and organize your itineraries. All your saved or booked properties are neatly organized under categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply go to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Head to the friendly city of Chester

Learn about the unique charm of Chester with a stay in a private vacation home. This welcoming city is known for its soccer games, university setting and restaurants. Xfinity Mobile Arena and Lincoln Financial Field are just a couple of the must-sees in the area. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Chester

Are you hoping to find attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Chester a fun place to get away. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Bridgeport Speedway (3 mi / 4.8 km)
  • Ice Works Skating Complex (3.6 mi / 5.8 km)
  • Gloucester County Dream Park (3.8 mi / 6.1 km)
  • South Philadelphia Sports Complex (10.6 mi / 17.1 km)
  • Aronimink Golf Club (11.5 mi / 18.6 km)
  • Philadelphia Zoo (12 mi / 19.2 km)

Exploring the natural landscape of Chester

Whether you're an outdoor enthusiast or just want to take in the scenery, Chester is a great place to spend some time outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Fort Mifflin (7.8 mi / 12.6 km)
  • Bartram's Garden (9.5 mi / 15.3 km)
  • Brandywine Valley (9.6 mi / 15.4 km)
  • Rockwood Park and Museum (10.2 mi / 16.4 km)
  • Nemours Mansion and Gardens (11.8 mi / 18.9 km)
  • Schuylkill River Trail (11.9 mi / 19.1 km)

Transportation to and around Chester

Fly into Philadelphia Intl. Airport (PHL), the closest airport, located 6.4 mi (10.3 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Wilmington, DE (ILG-New Castle), which is 17.6 mi (28.4 km) away.

If you'd rather travel by train, make your way to Chester Station or Chester Highland Avenue Station and explore the city from there.

Frequently asked questions

What is the best area to stay in Chester, Pennsylvania, United States of America when booking a vacation rental?
When considering a stay in Chester, Pennsylvania, a great area to explore is the waterfront neighborhood. This location offers a scenic view of the Delaware River and provides easy access to the beautiful Chester Waterfront Park, where you can enjoy leisurely strolls and picnics. Another appealing neighborhood is the historic downtown area, which is rich in cultural heritage and features attractions like the Chester Historical Society and the nearby Harrah's Philadelphia Casino and Racetrack, superb for entertainment and dining options.

In terms of vacation rentals, the waterfront neighborhood typically has a handful of properties available, allowing for a cozy and enjoyable stay. The downtown area also presents various options, focusing on both comfort and proximity to local attractions.

*Please play responsibly. You must be at least 21 years old to participate in any form of gambling in the United States. If you believe you have a gambling problem, seek help from professional organizations such as the National Council on Problem Gambling at www.ncpgambling.org or call their helpline at 1-800-522-4700.
How much does it cost to rent a vacation home in Chester?
Prices for vacation rentals in Chester 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 Chester 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 Chester vacation house rentals?
You can find great discounts on house rentals in Chester 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.
What is the most popular type of vacation rental accomodation in Chester?
In Chester, vacation houses are the most popular type of rental accommodation, with several available throughout the city. These homes provide a spacious environment, superb for families or groups seeking a comfortable stay. Most vacation houses include multiple bedrooms, fully equipped kitchens, and living areas, allowing guests to enjoy a home-like experience. Many properties also feature outdoor spaces, such as private yards or patios, ideal for relaxing after a day of exploring nearby attractions.
Are there any family house rentals in Chester?
In Chester, Pennsylvania, there are several family-friendly house rentals available, providing a great base for exploring the area. Visitors can find homes with spacious living areas, full kitchens for preparing meals, and outdoor spaces great for children to play in. Many properties also include modern amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for families.

The city is conveniently located near attractions like the Chester Waterfront and the nearby Brandywine Zoo, which can be enjoyable outings for families.
Can I find long-stay vacation rentals in Chester?
A long-stay vacation rental in Chester 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.
Are there any remote work vacation rentals in Chester?
In Chester, Pennsylvania, there are several remote work vacation rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties provide amenities tailored for remote workers, such as high-speed Wi-Fi and dedicated desk spaces, ensuring a productive environment. Travelers can expect comfortable accommodations with essential features, including fully equipped kitchens, spacious living areas, and sometimes outdoor spaces for relaxation.

Chester's proximity to Philadelphia offers additional attractions, with easy access to vibrant city life, historical sites, and local dining options. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chester 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.
What are popular rental amenities in Chester?
In Chester, popular vacation rental amenities include kitchens, allowing travelers to prepare their own meals with ease. Many properties also offer onsite parking, which is a significant convenience for those driving to the area. For business travelers or those needing to work remotely, rentals often come equipped with a desk and desk chair, providing a dedicated workspace. Additionally, coffee and tea makers are commonly found in these rentals, ensuring guests can enjoy a warm beverage at their leisure.
When is the best time to visit Chester for a vacation rental?
The best time to visit Chester for a vacation rental is during the peak season from May to July. This period draws many travelers eager to enjoy the vibrant setting and various outdoor activities that Chester has to offer. July stands out as the most popular month, where visitors can engage in the local culture and participate in summer events, all while basking in the pleasant weather.

During these warmer months, temperatures typically range from the low 60s to mid-80s Fahrenheit, making it ideal for leisurely strolls along the waterfront or exploring nearby attractions. The lively summer scene is superb for those seeking to engage with the community and take advantage of outdoor dining and recreational opportunities.

For travelers looking for a more budget-friendly experience, consider planning your visit in November. Although this month is quieter, it offers a unique charm as Chester transitions into the winter season. You can explore the area's rich history with fewer crowds, allowing for a more relaxed experience while enjoying local dining and attractions.

Ultimately, the best time to visit Chester depends on your preference for vibrant summer activities or a peaceful autumn getaway.
How early should I book a Chester vacation rental?
Book your Chester 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 Chester, Pennsylvania, United States of America?
In Chester, Pennsylvania, visitors can explore a variety of attractions highlighting the city's rich history and scenic waterfront. The Chester Waterfront Park offers beautiful views of the Delaware River and features walking trails, picnic areas, and a fishing pier, making it an ideal spot for outdoor activities. Nearby, the historic Chester City Hall, an impressive example of Romanesque architecture, stands as a testament to the city's past and is worth a visit.

The city is also home to the Harrah's Philadelphia Casino & Racetrack, which provides entertainment options ranging from gaming to dining. For those interested in local history, the Chester Historical Society offers insights into the city's heritage. Additionally, the nearby Widener University campus features beautiful grounds and is a focal point of community events.

*Please play responsibly. You must be at least 21 years old to participate in any form of gambling in the United States. If you believe you have a gambling problem, seek help from professional organizations such as the National Council on Problem Gambling at www.ncpgambling.org or call their helpline at 1-800-522-4700.
Can I change or cancel my Chester home rental booking on Vrbo?
To find Chester 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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chester vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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