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  2. Tennessee
  3. Chester County
  4. Rentals by Owner

Chester County Rentals by Owner

8.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
6.8 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Why Choose Rent By Owner for your Chester County 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 County

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here can enhance your experience, allowing you to enjoy the region's pleasant climate and vibrant local events while ensuring availability when booking a rental by owner through Rent By Owner.

Peak Season Highlights

spring
Spring (March to May)

During spring, the region comes alive with blooming flowers and mild weather, making it an ideal time for outdoor activities and exploring local scenery. Visitors often find this period perfect for enjoying the natural beauty without the summer crowds.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
autumn
Fall (September to November)

Autumn offers vibrant foliage and comfortable temperatures, providing a cozy atmosphere that enhances your stay. This is a popular season for those seeking scenic drives and outdoor explorations in the area with fewer visitors than peak summer months.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Summer (June to August)

Summer in this destination features warmer weather and longer daylight hours, attracting travelers looking to enjoy outdoor recreation. While it’s busier during this time, booking your rental by owner ensures a comfortable stay amid the lively summer atmosphere.

Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
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Winter (December to February)

The winter months bring cooler temperatures and a quieter environment, making it a peaceful time to visit if you prefer lower occupancy and more solitude. Take advantage of this off-peak season for a relaxed experience in the region's serene setting.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F

Weekly Weather Forecast for Chester County

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.

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 lounging with spacious patios or decks perfect for relaxing and taking in the scenic views.
  • Make the most of the region's natural beauty with private gardens or landscaped yards for peaceful outdoor escapes.
  • Take advantage of nearby lakes or rivers with access points for fishing, swimming, or kayaking adventures.
  • Benefit from outdoor grilling areas or fully equipped BBQ setups to enhance your outdoor dining experiences.
  • Explore the surrounding countryside with walking trails, hiking paths, or bike-friendly landscapes right at your doorstep.
  • Utilize outdoor fire pits or fireplaces ideal for cozy evenings under the stars.
  • Set up recreational equipment such as basketball hoops, volleyball courts, or horseshoe pits for fun-filled outdoor activities.
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Family Activities

  • Chester County Nature Trails: Explore scenic walking and biking paths perfect for family outings, allowing you to enjoy the region’s natural beauty.
  • Chester County Museum: Discover local history through engaging exhibits that offer an educational experience suitable for children and adults alike.
  • Chester County Park: Spend quality time outdoors at this spacious park with playgrounds, picnic areas, and open fields ideal for family recreation.
  • Local Festivals and Events: Participate in seasonal festivities and community events that provide entertainment and cultural insights into the region.
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Adult Activities

  • Fishing on the Tennessee River: You can enjoy a relaxing day casting your line in the region's renowned waters, known for their abundant fish species.
  • Exploring local parks and nature trails: The area offers scenic outdoor spaces perfect for hiking, birdwatching, or simply unwinding amidst nature’s beauty.
  • Visiting historical sites and museums: Discover the rich heritage of the region through its well-preserved landmarks and engaging exhibits.
  • Enjoying fine dining experiences: Indulge in the local cuisine at restaurants that showcase the flavors of this welcoming destination.

Other Places to Stay in Chester County, TN

Freed-Hardeman University
Jacks Creek
Chickasaw State Park
Chickasaw Golf Course

Chester County Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the area's natural scenery by engaging in outdoor pursuits such as hiking, fishing, or boating, which showcase the region's scenic beauty.
  • Visit nearby historic sites: Immerse yourself in the local culture by exploring historic landmarks and museums that highlight the area's rich heritage.
  • Sample regional cuisine: Enjoy authentic local flavors at nearby eateries or prepare delicious meals using fresh ingredients from area markets available in your rental.
  • Plan your trip around seasonal events: Check for festivals or community events happening during your stay to experience the area's vibrant local traditions firsthand.

Transportation Options

  • Rental Car Services: Convenient rental car options are available here, allowing you to explore the region at your own pace during your stay.
  • Local Taxi and Shuttle Services: Reliable taxi and shuttle providers operate throughout the area, making short trips and airport transfers straightforward.
  • Public Transportation: Although limited, local bus services offer an affordable way to navigate the nearby towns and attractions.
  • Private Transportation Providers: Customized private chauffeur services can be arranged for personalized travel around this destination.

Local Customs Options

  • Southern Hospitality:** Expect a warm welcome and friendly interactions as part of the area's local customs, making your stay here more inviting.
  • Community Events:** Participating in local festivals and gatherings is a cherished tradition that offers insight into the region's cultural identity.
  • Respect for Tradition:** Embracing long-standing customs and practices is appreciated when engaging with residents and exploring this destination.
  • Dining Etiquette:** Enjoying the regional cuisine often involves casual, family-oriented dining manners that reflect the area's laid-back vibe.

Frequently Asked Questions About Chester County Rentals by Owner

1. What are the top vacation rentals in Chester County?

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 51 in the Chester County 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 County. 

3. What is the cancellation policy for rental properties in the area?

Cancellation policies vary by listing, so it's important to review the specific terms provided by the owner on the rental page or contact them directly for details.

4. How do I contact the owner of a rental property in this destination?

You can reach out to the property owner through the messaging system provided on the booking platform to ask questions or clarify details before confirming your reservation.

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

Additional fees such as cleaning charges, service fees, or local taxes are often listed on the rental’s detail page. Be sure to review these before completing your booking.

6. What amenities are typically included in rentals by owner in this region?

Most rentals offer amenities like Wi-Fi, parking, and essential kitchen supplies, but specifics can differ. Check the listing details to confirm the features available at each property.

7. Is there a minimum stay requirement for rentals in this area?

Minimum stay requirements depend on the individual property owner and the booking period. Details are usually specified on the listing, or you can inquire directly with the owner.

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