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Historic South Hill Luxury Rentals

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Historic South Hill Pet Friendly Vacation Rentals

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8.0 (49 Reviews)
Bed & Breakfast
Lyndon House Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Historic South Hill Vacation Rental Homes?

What makes our Vacation Rentals 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.

Popular Areas for Historic South Hill Vacation Rentals

Where are the best neighborhoods to stay in Historic South Hill?

When planning your stay in Lexington, Kentucky, exploring neighborhoods like Historic South Hill offers a unique opportunity to experience the city's rich history and vibrant local culture. This charming area provides a welcoming atmosphere, making it an ideal choice for those seeking authentic experiences and convenient access to nearby attractions. Booking a vacation rental in Historic South Hill ensures you enjoy a comfortable and memorable visit, all within a neighborhood that beautifully combines historic charm with modern amenities. Discover the best of Lexington by choosing accommodations in this sought-after part of town, where southern hospitality meets timeless elegance.

Downtown

Centered in the heart of the city, this area offers vibrant streets and easy access to local amenities, making it an ideal choice for exploring Lexington's rich culture. Staying nearby provides a convenient base to enjoy the region's attractions and dynamic atmosphere.

View 741+ Rentals in Downtown

Best Times to Visit Historic South Hill

When should you plan your Vacation Rentals stay?

Timing your visit to this charming region can enhance your experience, so consider the best seasons when booking your vacation rentals here to enjoy its unique attractions and welcoming atmosphere at their finest.

Peak Season Highlights

spring
Spring (March to May)

During spring, the area experiences mild and inviting weather, making it an ideal time to explore local attractions in Lexington. This season attracts visitors seeking pleasant temperatures and vibrant scenery, perfect for enjoying your vacation rentals.

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

Autumn is a popular time to visit as the region's foliage displays stunning colors. The comfortable temperatures create a cozy atmosphere for exploring and relaxing at your chosen vacation rentals in this destination.

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

Off-Season Highlights

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Summer (June to August)

Summer tends to be busier with travelers enjoying warm weather, which can lead to higher demand for vacation rentals. If you prefer quieter surroundings, consider visiting early or late in the season when fewer visitors are around.

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

Visits during winter are less common, offering a chance to experience this destination with fewer crowds. While the temperatures are cooler, it's still suitable for those looking for a peaceful retreat at their vacation rentals.

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

Weekly Weather Forecast for Historic South Hill

How to Book Your Historic South Hill Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 Historic South Hill

More Top-Rated Vacation Rentals in Historic South Hill Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 a private outdoor patio or deck perfect for relaxing after exploring the area's historic sites.
  • Take advantage of spacious yards ideal for outdoor dining, picnics, or outdoor games in the region.
  • Stay active with access to well-maintained walking trails nearby, showcasing the natural beauty of this destination.
  • Benefit from outdoor seating areas designed for socializing and soaking up the local charm.
  • Make use of landscaped gardens that add to the scenic appeal of your stay here.
  • Secure parking facilities within the property for easy exploration around the region's attractions.
  • Find outdoor lighting features that extend your evenings into the peaceful ambiance of the surroundings.

Top Attractions Around Historic South Hill

What attractions are nearby?

Within this vibrant area, you can explore a variety of nearby activities such as local shops, dining options, and cultural attractions that showcase the charm of Lexington's historic South Hill neighborhood.

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Family Activities

  • Lexington Children's Museum: Engage your family with interactive exhibits that make learning fun for kids of all ages within this vibrant area.
  • Ky Horse Park: Discover the region’s renowned equestrian culture through guided tours and live demonstrations, perfect for family members interested in horse racing and riding.
  • Downtown Historic Tours: Explore the charming streets on a family-friendly walking tour that highlights Lexington's rich history and architecture.
  • Local Parks and Green Spaces: Relax and enjoy outdoor activities at nearby parks featuring playgrounds, picnic areas, and scenic trails suited for family outings.
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Adult Activities

  • Visit the Lexington History Museum: Dive into the region’s rich heritage by exploring exhibits that showcase the area's historical significance and cultural evolution.
  • Enjoy a guided walking tour of the historic district: Discover the charming architecture and storied streets of the neighborhood with a knowledgeable guide to enrich your experience.
  • Dine at local eateries: Savor regional flavors at restaurants renowned for their Southern hospitality and authentic Kentucky cuisine within the area’s vibrant culinary scene.
  • Explore local parks and green spaces: Relax in nearby parks that offer scenic views and tranquil environments, perfect for unwinding after a day of exploration.

Historic South Hill Travel Tips

How Can You Make the Most of Your Stay?

  • Embrace Local Charm: Take time to explore the neighborhood’s historic architecture and vibrant local shops to truly experience what makes this area unique.
  • Plan Your Dining Experience: Discover nearby cafes and eateries that showcase regional flavors, enhancing your stay with authentic tastes of Lexington.
  • Maximize Outdoor Activities: Visit nearby parks or scenic trails to enjoy the natural beauty surrounding this destination and create memorable outdoor moments.
  • Book Early for Popular Attractions: Secure your spot in sought-after tours or experiences well in advance to make the most of your visit here without missing out.

Transportation Options

  • Lextran Bus Service: The local bus system offers affordable and convenient transportation throughout the area, making it easy to explore nearby attractions from your vacation rental.
  • Taxi Services: Taxis provide quick and reliable point-to-point transport within the region, ideal for comfortably reaching local sights from your stay.
  • Rideshare Options: Rideshare apps like Uber and Lyft operate extensively here, offering flexible and on-demand transportation right at your fingertips.
  • Car Rentals: Renting a vehicle gives you the freedom to discover more remote parts of the region at your own pace, directly from your vacation rental location.

Local Customs Options

  • Southern Hospitality: Guests often experience warm welcomes and friendly interactions that reflect the region’s well-known southern hospitality during their stay.
  • Historic Preservation Customs: You’ll notice a deep appreciation for preserving architectural heritage, with local ordinances supporting the maintenance of historic buildings in this area.
  • Local Food Traditions: It’s common to indulge in dishes rooted in Kentucky’s culinary history, celebrating traditions like bourbon-infused recipes and Southern comfort food.
  • Community Events: Participating in neighborhood gatherings and festivals is a cherished tradition that fosters a strong sense of community here.

Frequently Asked Questions About Historic South Hill?

1. What are the top vacation rentals in Historic South Hill?

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

2. How many vacation rentals have private pools in Historic South Hill?

There are 10 vacation rentals with private pools near Historic South Hill. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Historic South Hill are best for families?

If you are looking for a family-friendly vacation home in Historic South Hill, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Historic South Hill:

4. How many Rentbyowner vacation rentals are available in Historic South Hill?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 593 in the Historic South Hill 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 Historic South Hill. 

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

Cancellation policies vary depending on the individual property owner. You should review the specific listing details or contact the owner directly to understand the terms related to cancellations and refunds.

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

Additional fees such as cleaning, service charges, or security deposits are typically outlined on each listing. To avoid surprises, it’s best to read the full details provided or reach out to the property owner for clarification.

7. How do I check the availability of vacation rentals in this destination?

Availability is updated regularly on the booking platform. You can select your preferred dates and view real-time availability by searching through the listing pages or contacting the property owner for confirmation.

8. Can I modify or extend my stay after booking a vacation rental in this region?

Modifications or extensions depend on the individual property owner’s policies. It’s recommended to contact the owner directly as early as possible to discuss any changes to your reservation.

9. What amenities are generally included in vacation rentals here?

Most vacation rentals provide amenities like Wi-Fi, kitchen facilities, and parking, but specific offerings vary. To ensure the property meets your needs, review the listed amenities carefully or ask the owner directly before booking.