Chester holiday rentals

We found 2 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 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.

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  • All the privacy of home

    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)
  • 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)

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:

  • Kinkaid Lake (21.6 mi / 34.7 km)
  • Moro Island (10.8 mi / 17.4 km)
  • Saint Marys Lake (13.9 mi / 22.3 km)
  • Pere Marquette Park (14 mi / 22.6 km)
  • Kaskaskia River State Fish and Wildlife Area (21 mi / 33.8 km)
  • Elzie C. Segar Memorial Park (0.9 mi / 1.4 km)

Frequently asked questions

What is the best area to stay in Chester when booking a holiday rental?
When considering a holiday rental in Chester, Illinois, a delightful area to stay is the charming downtown district. This neighbourhood offers a pleasant mix of historical charm and modern conveniences, making it an attractive option for visitors. You can explore the picturesque surroundings and enjoy the local eateries and shops that contribute to its vibrant setting.One of the top attractions nearby is the historic Chester Bridge, which not only provides stunning views of the Mississippi River but also serves as a lovely backdrop for leisurely walks. Additionally, the nearby Fort Kaskaskia State Historic Site offers a glimpse into the region's rich history, showcasing remnants of the fort and providing access to scenic picnic areas.In terms of accommodation, the downtown area features a range of properties, from quaint apartments to cosy homes, ensuring a variety of options to suit different preferences and budgets.
What are the top attractions in Chester?
In Chester, Illinois, visitors can explore a number of charming attractions that reflect the town's rich history and natural beauty. The Chester Bridge offers picturesque views of the Mississippi River, making it a lovely spot for photography and leisurely walks. The nearby Fort de Chartres State Historic Site is a fascinating destination, showcasing the remnants of an 18th-century fort and offering insights into the area's historic past.The town's picturesque downtown area features unique shops and local eateries that provide a taste of Chester's small-town charm. Additionally, the nearby Shawnee National Forest offers outdoor enthusiasts opportunities for hiking, birdwatching, and enjoying the scenic views of forests and bluffs. The annual Chester Pumpkin Festival is also a highlight, celebrating the community's spirit with various activities and attractions for all ages.
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.

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