Chester holiday homes

We found 179 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Chester that are perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as air conditioning and a pool. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

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The arty city of Chester awaits you

Enjoy the art galleries and other features of Chester. Well known for its restaurants, shopping and bird watching, this welcoming city won't disappoint. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Chester

Are you searching for attractions to see in the city? Venture out of your cosy holiday rental and experience everything that makes Chester a fun spot to go on holiday. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Pocahontas State Park (7.2 mi / 11.6 km)
  • Libby Hill Park (11.9 mi / 19.2 km)
  • The Barns of Kanak (13.3 mi / 21.3 km)
  • Virginia Motorsports Park (13.9 mi / 22.4 km)
  • Country Club of Virginia (15.5 mi / 24.9 km)
  • Richmond Raceway (16.8 mi / 27 km)

Exploring the natural features in Chester

Whether you're an adventurous traveller or just want to take 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 sights, all within 30 miles (48.2 km) of the city centre:

  • Dorey Park (9.6 mi / 15.4 km)
  • Virginia Capital Trail: Richmond Trailhead (11.8 mi / 19 km)
  • Libby Hill Park (11.9 mi / 19.2 km)
  • James River (12.1 mi / 19.5 km)
  • Pamplin Historical Park (12.2 mi / 19.6 km)
  • Maymont Park (12.5 mi / 20.1 km)

Transport options to and around Chester

The nearest airport is in Richmond, VA (RIC-Richmond Intl.), located 12.2 mi (19.6 km) from the city centre.

Frequently asked questions

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 approximately 14 available throughout the area. These homes typically provide ample space for families or groups, featuring multiple bedrooms, fully equipped kitchens, and cosy living areas. Many also include outdoor spaces for relaxation and gatherings. Additionally, there are several mobile homes and cottages scattered around, offering alternative choices for travellers seeking a more great experience.
Are there any family house rentals in Chester?
In Chester, Virginia, there are several family-friendly house rentals available, making it a great choice for those travelling with children. The area features a variety of homes that often include spacious living rooms, full kitchens for preparing family meals, and outdoor spaces where kids can enjoy playtime. Many properties are equipped with essential amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for guests.Visitors will find that Chester is conveniently located near several parks, providing ample opportunities for outdoor activities and family outings. Nearby attractions like the Chesterfield County Museum offer a glimpse into local history, while the scenic waterways along the James River present options for fishing and picnicking.
Can I rent a holiday home with a pool or hot tub in Chester?
In Chester, Virginia, there are several holiday homes available for rent that feature pools and hot tubs, providing great options for travellers seeking relaxation and comfort. Many of these properties are located in charming residential neighbourhoods, offering a peaceful environment while still being close to local amenities and attractions.Rentals typically come with a variety of amenities, including private swimming pools, hot tubs, spacious outdoor areas for entertaining, and fully equipped kitchens ideal for family meals. Some properties may also feature additional comforts such as Wi-Fi, air conditioning, and comfortable living spaces.
Are there pet-friendly house rentals in Chester?
In Chester, Virginia, there are several pet-friendly house rentals available, offering a comfortable stay for travellers accompanied by their furry friends. Many of these properties come equipped with essential amenities such as spacious kitchens, comfortable living areas, and private outdoor spaces, ideal for both relaxation and entertaining.The area is conveniently located near parks and recreational spaces, providing opportunities for walks and outdoor activities with pets. Notably, the nearby Chester Park features walking trails and open areas, making it a lovely spot for pet owners to enjoy time outdoors. Additionally, the charming neighbourhood has local shops and eateries that may welcome pets, enhancing the overall experience for visitors.
Are there any remote work holiday rentals in Chester?
In Chester, Virginia, there are several remote work holiday rentals available, with around 14 properties suited for those needing a productive environment. These rentals typically come equipped with essential amenities such as reliable Wi-Fi, dedicated desk spaces, and comfortable office chairs, allowing for a seamless work-from-home experience. Many properties also feature ample living areas for relaxation after work hours.Chester is conveniently located near Richmond, offering easy access to local attractions, dining options, and outdoor spaces for leisure activities. The area is known for its pleasant neighbourhoods and community parks, providing a balance between work and recreation. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Chester?
In Chester, popular holiday rentals typically feature a range of amenities that cater to comfort and convenience. Most properties come equipped with kitchens, allowing guests to prepare their own meals, and many include onsite parking for easy access. Outdoor spaces such as patios and gardens are common, providing a pleasant area for relaxation. Additionally, a fireplace is often included, adding a cosy touch for those cooler evenings.
When is the best time to visit Chester for a holiday rental?
The best time to book a holiday rental in Chester is during the peak season from May to July, with July being the most popular month. This vibrant period draws visitors who are keen to explore Chester's charming parks and partake in various outdoor activities while enjoying the warm, sunny weather. Daytime temperatures often reach the mid to high 30s Celsius, creating an ideal setting for family picnics, leisurely strolls, and community events.During these summer months, Chester comes alive with a range of festivals and local happenings that cater to adventure seekers and families alike. The lush greenery of the parks and the inclusive setting make it a superb backdrop for outdoor fun and socialising with other travellers.For those looking for a more budget-friendly option, December presents a wonderful opportunity to visit Chester. While this month falls in the low season, it offers a unique charm with festive decorations and a quieter pace, allowing visitors to enjoy a more relaxed exploration of the area, including cosy cafés and local shops.Ultimately, your best choice depends on whether you prefer the lively buzz of summer activities or the peaceful ambience of winter.
What are the top attractions in Chester?
In Chester, Virginia, visitors can explore several attractions that highlight the area's rich history and natural beauty. One of the main draws is the Historic Chesterfield County Courthouse, which offers a glimpse into the region's past and is surrounded by picturesque grounds. The nearby Iron Bridge Sports Park provides ample opportunities for outdoor activities, including walking trails and sports facilities, making it a popular spot for families and active visitors.For those interested in nature, the Appomattox River is a significant feature, offering scenic views and recreational activities such as fishing and kayaking. The area also hosts several local parks, such as the Chester Park, which is equipped with playgrounds and picnic areas, great for a relaxing day outdoors.
Are all fees included in the Chester holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Chester holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Chester holiday homes?
You can find great discounts on holiday homes in Chester on Bookabach, 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.
Can I change or cancel my Chester holiday home booking on Bookabach?
To find Chester holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Chester?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Chester holiday home?
Book your Chester holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chester?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Chester to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.