Chester holiday homes, SD, USA: holiday houses & more

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.

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House

Condo/Apartment

Find the best place to stay - Chester

Lake Madison Condo

Sleeps 4 · 1 bedroom · 1 bathroom

The Grandview Lake House, Dog Friendly, Near Lake Madison, Outdoor Patio

Sleeps 9 · 2 bedrooms · 1 bathroom

Cabin on Lake Madison! 100 ft of shoreline, walking distance to Hillside Resort!

Sleeps 4 · 2 bedrooms · 1 bathroom

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:

Rocky Run Golf Course (10.7 mi / 17.2 km)
Lakes Golf Course (4.3 mi / 6.9 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)
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)
Sioux River Red Rock Trail Bridge (12 mi / 19.3 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 most popular type of holiday home accommodation in Chester?

Cabins are the most popular kind of holiday home in Chester, according to our data. Even if you’ve got something different in mind, Bookabach has properties in all shapes and sizes. Take a look at our options to find your ideal match.

How much does it cost to rent a holiday home in Chester?

The average price for a holiday home in Chester is based on several factors, like property type, length of stay and season. Whether you’re in search of a sprawling villa with space for the whole family or a quaint cottage just enough for two, just add your dates of travel to view stays with terrific value.

How much does it cost to rent a beach house in Chester?

The average price for a holiday home near the beach in Chester depends on when you’re travelling and the size and style of property you’re looking for. Find prices easily on Bookabach by entering your travel dates and destination. Then use our filters to select the number of bedrooms and amenities that you prefer, such as WiFi, a pool and air conditioning.

What are popular home amenities in Chester?

Some of the most popular home amenities people look for in Chester are a firepit, a lake view and a nearby waterfront. Whether you’re hitting the road with friends, family or even pets, Bookabach holiday homes feature the best amenities for ultimate relaxation with the people closest to you.

What are the top attractions for families in Chester?

Keeping the kids happy during your Chester holiday is a cinch with these leading family-friendly attractions:

Lake Madison
Walkers Point Recreation Area
Lakes Golf Course

How old do you have to be to rent a holiday home in Chester?

The minimum age requirements can vary across properties on Bookabach, so look at the rules of the holiday home in Chester you want. But usually, it’s 16, 18 or 21.

How long can I rent a holiday home in Chester for?

The amount of time you can stay in a Chester holiday home for is down to the property. Just tap in your preferred travel dates to view options offering longer term stays. They have the things you need to make your extended getaway more enjoyable and convenient, like air conditioning and laundries. Some properties might also offer weekly or monthly discounts, so you can stay even longer for less.