Chester holiday rentals

We found 25 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Chester that are perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

  • 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, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Chester getaway

Learn about the unique charm of Chester with a stay in a holiday home rental. This city has something for everyone. 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

Do you want to discover top things to see and do while you're in town? Venture out of your cosy holiday rental and check out everything that makes Chester a fun place to get away to. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Lakes Golf Course (4.3 mi / 6.9 km)
  • Rocky Run Golf Course (10.7 mi / 17.2 km)
  • Madison Golf & Country Club (15 mi / 24.2 km)

Exploring the natural landscape of Chester

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Chester. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Madison (6.4 mi / 10.3 km)
  • Lake Herman State Park (13.6 mi / 21.9 km)
  • Sioux River Red Rock Trail Bridge (12 mi / 19.3 km)
  • Porter Sculpture Park (20.3 mi / 32.7 km)
  • Walkers Point Recreation Area (6.5 mi / 10.5 km)
  • Brown Memorial Park (11.8 mi / 19 km)

Transport to and around Chester

The nearest airport is in Sioux Falls Regional Airport (FSD), located 23.8 mi (38.3 km) from the city centre.

Frequently asked questions

What is the best area to stay in Chester when booking a holiday rental?
When considering a holiday rental in Chester, South Dakota, the area surrounding the charming downtown is particularly appealing. This neighbourhood not only offers a quaint atmosphere but also provides easy access to local attractions such as the scenic Lake Vermillion, superb for outdoor enthusiasts looking to fish or enjoy a peaceful day by the water. Nearby, you'll find the Chester Museum, which offers insights into the town's rich history and culture.The downtown area features a variety of properties, giving visitors a selection that ranges from cosy cabins to larger family homes. Staying here allows you to immerse yourself in the local community while being conveniently located to explore the surrounding natural beauty.
What are the top attractions in Chester?
In Chester, South Dakota, visitors can enjoy a variety of attractions that highlight the charm of this small town. The Chester City Park is a lovely spot for outdoor activities, featuring picnic areas, a playground, and open green spaces superb for relaxation. The park often hosts community events and is a gathering place for locals and visitors alike.The nearby Lake Madison offers opportunities for fishing, boating, and enjoying the scenic beauty of the water, making it a great destination for nature lovers. Additionally, the Chester Museum provides insights into the town's history, showcasing local artifacts and memorabilia that reflect the area's heritage.For those interested in local wildlife and outdoor adventures, the surrounding countryside offers beautiful landscapes and trails for hiking and exploring.
Are all fees included in the Chester holiday homes prices shown on Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Chester holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Chester to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.