Chester, Illinois holiday accommodation: short-term house rentals & properties

Discover a selection of holiday rentals in Chester that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find the best place to stay - Chester

Secluded Private Cabin with Pool, hot tub, fireplace & so much more

Sleeps 16 · 5 bedrooms · 3+ bathrooms

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Enjoy full kitchens, laundry, pools, gardens and more
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The cosy area of Chester awaits your stay

The area's opera and entertainment are just some of the reasons to come on holiday to Chester. Travellers especially like the golfing, parks and restaurants in this welcoming and walkable city. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Chester

Are you hoping to discover attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Chester a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

Sainte Genevieve Winery (13 mi / 20.9 km)
Cave Vineyard (16.4 mi / 26.4 km)
Perryville Country Club (14.4 mi / 23.1 km)
Sparta Country Club (15.1 mi / 24.4 km)
The Bluffs Vineyard and Winery (20.9 mi / 33.7 km)
Chester Skating Rink (1.2 mi / 2 km)

Exploring the natural landscape of Chester

Whether you're an adventurous traveller or just want to take in the scenery, Chester is a great spot to appreciate mother nature. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

Pyramid State Recreation Area (24.4 mi / 39.3 km)
Elzie C. Segar Memorial Park (0.9 mi / 1.4 km)
Randolph County State Recreation Area (4.6 mi / 7.4 km)
Kaskaskia River State Fish and Wildlife Area (21 mi / 33.8 km)
Paul Ice Recreation Area (23.4 mi / 37.6 km)

Frequently asked questions

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

Property type, length of stay and season are some things that can influence the price of a holiday home. Simply click on your travel dates to find your perfect fit. From cosy chalets to sprawling villas, all Stayz holiday homes provide amazing value.

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

Prices for beach houses in Chester differ depending on the size and style of the property and when you plan to travel. All you need to do is enter your travel dates into Stayz and how many guests to view your holiday home options and prices. From there you can use our filters to narrow your search by nearby activities, amenities, ratings and more.

What are the top attractions for families in Chester?

You'll find lots of cool things to see and do with the family in Chester, such as:

Chester Skating Rink
Randolph County State Recreation Area
Marys River Covered Bridge

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

The minimum age can differ across properties on Stayz, so look at the rules of the holiday home in Chester you're considering. But in general, it's 16, 18 or 21.

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

The length of time you can rent a holiday home in Chester depends on the property. Just enter your selected travel dates to view a list of options offering extended stays. With a range of creature comforts like washing machines and kitchens, as well as some offering discounted weekly or monthly prices, you're sure to get someplace just right to call your home away from home in Chester.