1. USA
  2. South Dakota
  3. Chester
  4. Rentals by Owner

Discover Your Perfect Chester Rentals by Owner

Chester Rentals by Owner

More Top-Rated Rentals by Owner in Chester Area

Why Choose Rent By Owner for your Chester vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Chester

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here can enhance your experience, as this destination offers seasonal charm that caters to various interests and preferences throughout the year.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, you'll experience the region's warmest weather, ideal for outdoor activities and enjoying the natural beauty of the area. This season attracts visitors looking to make the most of pleasant temperatures before the peak heat sets in.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
autumn
Early Fall (September to October)

This period offers cooler temperatures and vibrant fall foliage, making it a popular choice for travelers seeking scenic views and comfortable weather while exploring the region’s attractions.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Mid Winter (December to February)

During these colder months, fewer visitors venture here, providing a quieter experience for those seeking tranquility and lower rental rates during the off-peak season.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 5°F to 15°F
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Early Spring (March to April)

As the region transitions from winter, this timeframe sees fewer travelers, offering a peaceful retreat with gradually warming weather suitable for off-season rental stays.

Average Temperature Daytime: 40°F to 55°F - Nighttime: 25°F to 35°F

Weekly Weather Forecast for Chester

How to Book Your Chester vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Chester

More Top-Rated Rentals by Owner in Chester Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining areas perfect for family meals or gatherings in the region's charming surroundings.
  • Benefit from spacious yards ideal for outdoor games, relaxation, or simply soaking in the natural beauty of the area.
  • Relax on a private porch or deck that offers stunning views of the scenic landscape around here.
  • Take advantage of outdoor fire pits for cozy evenings and making memories under the stars.
  • Explore well-maintained gardens that provide a tranquil setting for your outdoor experience.
  • Utilize designated grilling stations to prepare delicious meals amidst the fresh air of this destination.
  • Discover nearby walking or hiking trails accessible directly from the rental, immersing you in the area's natural charm.

Top Attractions Around Chester

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities and local attractions that showcase the region’s natural beauty and small-town charm, making it an ideal destination for your next vacation rental by owner experience.

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Family Activities

  • Chester City Park: Enjoy a family picnic or outdoor games at this scenic park, perfect for relaxing and engaging activities in the area.
  • Local Heritage Museum: Discover the region’s history through interactive exhibits that offer educational fun for all ages.
  • Nature Trails: Explore nearby walking and biking trails that provide an excellent way to experience the natural beauty of the region with your loved ones.
  • Community Events: Participate in seasonal festivals and local gatherings held throughout Chester, offering memorable experiences for families visiting here.
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Adult Activities

  • Chester County Historical Society: Discover the area's rich history through engaging exhibits and preserved landmarks that provide insight into the region's past.
  • The Local Art Gallery: Explore inspiring contemporary and traditional artworks created by local artists, offering a unique cultural experience in this destination.
  • Nature Trails and Parks: Enjoy outdoor activities such as hiking and birdwatching along scenic trails that showcase the natural beauty of the region.
  • Community Events and Festivals: Participate in seasonal festivals and local gatherings that highlight the area’s vibrant community spirit and traditions.

Other Places to Stay in Chester, SD

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Chester Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the area's natural landscapes by engaging in outdoor pursuits that showcase the region’s unique scenery.
  • Connect with your rental host: Communicate directly with the owner to receive personalized tips and ensure your stay aligns perfectly with your interests.
  • Discover hidden gems nearby: Use your rental's location to uncover lesser-known spots that offer authentic experiences away from typical tourist routes.
  • Plan your transportation wisely: Arrange convenient travel options within the area to make exploring the region seamless and enjoyable during your visit.

Transportation Options

  • Car Rentals: Renting a vehicle offers the flexibility to explore this area and its surrounding scenic routes at your own pace.
  • Local Taxi Services: Reliable taxi services in the region provide convenient transportation options for quick trips or airport transfers.
  • Public Transportation: Local bus networks serve the area, making it easy to navigate without the need for a personal vehicle.
  • Bike Rentals: Biking is a popular way to enjoy the peaceful surroundings and scenic countryside here at a leisurely pace.

Local Customs Options

  • Welcoming Community Events: You’ll find that participating in local gatherings offers an authentic way to connect with residents and experience the area's friendly hospitality.
  • Traditional Farming Practices: The region’s longstanding agricultural customs provide insight into the area's history and are often celebrated through seasonal festivals.
  • Regional Cuisine:** Savoring local dishes prepared with fresh, regional ingredients gives you a taste of the area's cultural heritage and community spirit.
  • Respect for Nature: Maintaining the natural landscape is a valued custom, encouraging visitors to engage in outdoor activities responsibly and sustainably.

Frequently Asked Questions About Chester Rentals by Owner

1. What are the top vacation rentals in Chester?

There are a lot of options in Chester. If you plan on staying in the Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chester:

2. How many Rentbyowner vacation rentals are available in Chester?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 19 in the Chester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chester. 

3. What is the cancellation policy for rentals in this area?

Cancellation policies vary by listing, so it’s best to review the specific rental's terms on its page or contact the owner directly to understand any fees or restrictions.

4. How do I book a rental by owner in this destination?

You can easily book your stay through Rent By Owner’s platform by selecting your preferred dates and contacting the owner directly from the listing for confirmation and additional details.

5. Are there any additional fees I should be aware of when booking here?

Additional fees such as cleaning or service charges are typically listed on the rental page. Always review the total cost before completing your reservation or reach out to the owner for clarification.

6. What amenities are usually included in rentals by owner here?

Amenities vary by property but commonly include essentials like Wi-Fi, kitchen appliances, and parking. Check each listing’s description for a detailed list of what is included during your stay.

7. How can I communicate with the owner of my rental in this region?

You can contact the owner directly through the messaging feature on Rent By Owner’s platform, allowing you to ask questions and coordinate your stay seamlessly.

More Rentals You May Like Near Chester

More Top-Rated Rentals by Owner in Chester Area