Chester holiday lettings

We found 279 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Chester that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you expect for your stay, including Wi-Fi and parking. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Chester

Showing deals for:10 Jul - 17 Jul

Image gallery for 4 Bedroom Home, Game Room & Pool in a Quiet Upscale Neighborhood

Pool
9.2 out of 10, Wonderful, (7 reviews)
Wonderful
(7 reviews)

4 Bedroom Home, Game Room & Pool in a Quiet Upscale Neighborhood

Bryn Mawr

8% off
Price is £57,554
for 7 nights, 1 home
£8,222 per night
includes taxes & fees
4 Bedroom Home, Game Room & Pool in a Quiet Upscale Neighborhood

Find spaces that suit your style

  • 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

Head to the friendly city of Chester

Learn about the unique charm of Chester with a stay in a holiday home rental. This welcoming city is known for its football matches, university setting and restaurants. Lincoln Financial Field and Pennsylvania Convention Center are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Chester

Are you hoping to discover attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Chester a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Chester. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport to and around Chester

Fly into Philadelphia International Airport (PHL), the closest airport, located 6.4 mi (10.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Wilmington, DE (ILG-New Castle), which is 17.6 mi (28.4 km) away.

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

Frequently asked questions

How much does it cost to rent a holiday home in Chester?
Prices for holiday 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 holiday 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 holiday rental accomodation in Chester?
In Chester, holiday houses are the most popular type of holiday rental, with around 10 available throughout the area. These homes typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups. Many of these properties also offer outdoor spaces, such as gardens or patios, where guests can relax and enjoy the surrounding environment.
Are there any family house rentals in Chester?
In Chester, Pennsylvania, there are several family-friendly house rentals available, making it a great choice for those travelling with children. The area features various homes that often come equipped with spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for kids to enjoy. Many properties also include amenities like Wi-Fi and air conditioning to ensure a comfortable stay.

Visitors can explore nearby attractions such as the picturesque Chester Waterfront and the stimulating interactive exhibits at the nearby Delaware County Institute of Science. The locale's proximity to Philadelphia provides additional opportunities for day trips, allowing families to experience the rich history and vibrant culture of the city.
Can I find long-stay holiday rentals in Chester?
A long-stay holiday rental in Chester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work holiday rentals in Chester?
In Chester, Pennsylvania, there are several holiday rentals available that cater to remote workers. These properties typically offer essential amenities such as Wi-Fi, with many units providing free internet access directly in the rooms. Additionally, you can expect to find spaces equipped with desks, allowing for a comfortable work environment.

Chester itself is conveniently located near points of interest, including the scenic Delaware River and local parks, providing opportunities for relaxation after work hours. The area has a blend of urban and natural charm, making it a great choice for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chester holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chester with parking available—perfect for families or travellers 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 rental amenities include well-equipped kitchens, which allow guests to prepare their own meals, and onsite parking for convenience. Many holiday rentals also feature coffee and tea makers, providing a comforting touch for morning routines. Additionally, accommodations often come with desks and desk chairs, suiting travellers who may need to work during their stay.
When is the best time to visit Chester for a holiday rental?
The peak travel season in Chester occurs from May to July, with July being the most popular month for visitors. This is a vibrant time in the city, as families and friends gather to enjoy outdoor events, festivals, and warm-weather activities. With temperatures typically ranging from 20 to 30 degrees Celsius, it's ideal for exploring the local parks, embarking on riverside strolls, or enjoying al fresco dining at one of the many charming restaurants.

During this bustling season, Chester is lively and full of energy, making it a great time for those looking to immerse themselves in the community spirit and take advantage of the numerous attractions available.

For those seeking a more budget-friendly experience, November is an excellent option. While the weather is cooler, with temperatures dropping to around 5 to 10 degrees Celsius, visitors can enjoy a quieter atmosphere and take advantage of lower rental rates. This month also offers a unique opportunity to explore Chester's historical sites and local culture without the crowds, giving you a more intimate experience of the city.
How early should I book a Chester holiday rental?
Book your Chester holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chester?
In Chester, Pennsylvania, visitors can explore several top attractions that reflect the city's rich history and culture. The Chester Waterfront Park offers scenic views of the Delaware River, making it a lovely spot for a leisurely stroll or a picnic. Nearby, the historical district features the impressive Chester City Hall, an architectural gem that showcases the city's past.

For those interested in history, the Harriet Tubman Museum is a significant site dedicated to the legacy of the famed abolitionist, while the nearby Brandywine Zoo provides family-friendly fun with a variety of animals and educational programs.

Moreover, the city is close to the Widener University campus, which often hosts events and exhibitions open to the public, enhancing the cultural landscape of Chester.
Can I change or cancel my Chester home rental booking on Vrbo?
To find Chester holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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.

More holiday ideas