Chesterfield vacation rentals

We found 16 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Chesterfield that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the amenities you need and want for your stay, which might include WiFi and a fireplace. No matter what you're looking for, you'll be able to choose a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find out more about Chesterfield

Find out more about Chesterfield

Why visit Chesterfield

  1. Outdoor Adventures: Chesterfield offers a variety of outdoor activities in beautiful parks and nature reserves, perfect for hiking and exploring.
  2. Scenic Relaxation: Experience the charm of picturesque neighborhoods, ideal for a romantic getaway or a peaceful retreat.
  3. Cultural Experiences: Discover local galleries and educational sites that showcase the area's rich history and artistic heritage.
  4. Cozy Accommodations: Choose from a range of vacation rentals, from charming cabins to comfortable flats, catering to all travellers.
  5. Welcoming Atmosphere: Enjoy the friendly hospitality of Chesterfield, making your visit warm and memorable.

Popular types of accommodation in Chesterfield

Discover the perfect getaway in Chesterfield with our diverse selection of vacation rentals. Whether you’re looking for houses, charming cabins, or cozy cottages, we have options that cater to every traveller’s needs. From Chesterfield holiday rentals to comfortable apartments, our listings offer transparency and savings to ensure a stress-free experience. Explore the best rental properties in Chesterfield and find your ideal home away from home!

  • Houses: The top choice for visitors to Chesterfield, these homes offer a comfortable and spacious setting for families, couples, or groups of friends.
  • Cabins: A popular option for those seeking a rustic escape, cabins provide a unique retreat amidst nature.
  • Cottages: Charming and quaint, cottages are ideal for a cozy getaway in a picturesque environment.
  • Caravan Parks: For a more adventurous stay, caravan parks offer a fun option for travellers looking to connect with the outdoors.
  • Apartments: Convenient and practical, apartments are a great choice for those looking for a home-like atmosphere during their visit.**

Top attractions in Chesterfield

Chesterfield, South Carolina, offers a delightful mix of outdoor adventures, scenic views, and romantic getaways. Visitors can explore local attractions like national and state parks, educational sites, and galleries, perfect for those seeking cultural experiences or family fun. Don't forget to request tours to enhance your visit and make the most of what this charming area has to offer.

  1. Cheraw State Park: This stunning state park, located 19.3km from Chesterfield, offers a unique blend of adventure and natural beauty, perfect for outdoor enthusiasts. Enjoy hiking, fishing, and scenic views that showcase the area's lush landscapes.
  2. Granny Hollow Pottery and Fancy Crafts: Situated 25.7km away, this charming gallery celebrates local culture through exquisite pottery and craftwork. It's a great place to appreciate artistry and maybe even take home a unique souvenir.
  3. Northeastern Technical College: Just 14.5km from Chesterfield, this educational institution embodies cultural vibes, often hosting events and activities that engage the community and foster learning.

Things to do recommended for families

Families can explore the serene H Cooper Black Jr. Memorial Field Trial & Recreation Area, located 24.1km from Chesterfield, or unwind at Little Park, 27.4km away, both offering wellness and relaxation vibes perfect for a memorable family getaway.

Things to do recommended for groups

Experience the scenic Cheraw State Park Golf Course, located 19.3km from Chesterfield, where your group can enjoy a day of golfing amidst beautiful outdoor settings. It's perfect for sports enthusiasts looking to bond over a friendly game in the heart of nature.

What do I need to keep in mind when booking a vacation in Chesterfield

When you're planning a trip—whether it's with friends, family, your pets, or for an extended stay—be sure to prioritize your preferences when filtering options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Chesterfield with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Chesterfield with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, as well as access to age-appropriate facilities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Chesterfield: For many families, a vacation isn't truly enjoyable without their beloved furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Chesterfield: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Chesterfield

Chesterfield, South Carolina, offers a delightful blend of outdoor adventures and charming scenery, perfect for a romantic getaway. Explore nearby neighborhoods that exude historical charm and relaxation, with options for cozy vacation rentals and luxurious flats. Friendly and welcoming, Chesterfield invites you to soak in its serene atmosphere while discovering the best spots for a memorable escape. Whether you’re wandering through the scenic districts or enjoying local hospitality, Chesterfield promises a unique travel experience.

  • Cheraw: Cheraw is a charming city located 19.3km from Chesterfield, renowned for its outdoor activities and scenic beauty. Visitors flock to Cheraw for its beautiful golf courses and recreational areas that offer a range of sports options. The nearby national state park and picturesque lakes provide perfect opportunities for hiking, fishing, and picnicking. Additionally, the local racetrack draws motorsport enthusiasts, making it a lively spot for events and races. Whether you're enjoying a day in nature or engaging in recreational activities, Cheraw promises a delightful experience.
  • Ruby: Located a mere 8.0km from Chesterfield, Ruby is a vibrant city where sports and culture intersect. This small town is particularly known for its motor racing events, attracting fans from near and far. Ruby is also home to several historic sites and a convention centre that hosts various cultural events and business gatherings. The rich history and community spirit make Ruby an engaging stop on your journey, offering both excitement and a glimpse into the local culture.
  • Mount Croghan: Just 12.9km away from Chesterfield, Mount Croghan is a hidden gem perfect for those seeking romance and outdoor adventures. The city's scenic landscapes and tranquil lakes create a serene backdrop for a romantic getaway or a peaceful day outdoors. Visitors can enjoy motor racing and explore recreational areas that promise fun and excitement. The local historic sites and charming ships add to the allure, making Mount Croghan an excellent choice for a picturesque escape filled with nature and history.

Best time to go to Chesterfield

If you're planning a trip to Chesterfield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in February, May and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January43.5°F (6.4°C)Light RainMostly SunnyAverageSlightly Low
February47.5°F (8.6°C)Light RainMostly SunnySlightly HighSlightly Low
March53.8°F (12.1°C)Light RainMostly SunnyAverageSlightly Low
April62.4°F (16.9°C)Light RainMostly SunnyAverageAverage
May70.5°F (21.4°C)Light RainMostly SunnySlightly HighAverage
June77.7°F (25.4°C)Light RainMostly SunnyAverageSlightly High
July80.8°F (27.1°C)Light RainMostly SunnyAverageAverage
August79.0°F (26.1°C)Light RainMostly SunnyAverageAverage
September73.9°F (23.3°C)Light RainMostly SunnySlightly HighAverage
October63.9°F (17.7°C)Light RainMostly SunnySlightly LowSlightly High
November53.1°F (11.7°C)Light RainMostly SunnySlightly LowSlightly High
December47.8°F (8.8°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next escape? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for planning your travel. You can easily start new trips, resume your previous ones, or manage your existing plans all in one place. Your saved or booked properties will be neatly arranged under categories like Potential, Upcoming, or Current Trips. To begin exploring the benefits of Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Chesterfield getaway

Learn about the unique charm of Chesterfield with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Chesterfield

Are you looking for attractions to visit during your stay? Venture out of your vacation home and experience everything that makes Chesterfield a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Cheraw State Park Golf Course (12.3 mi / 19.7 km)
  • Granny Hollow Pottery and Fancy Crafts (15.8 mi / 25.4 km)

Exploring the natural features in Chesterfield

Whether you're looking for adventure or just want to take in the scenery, Chesterfield is a great place to get out in nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Cheraw State Park (11.7 mi / 18.8 km)
  • H Cooper Black Jr. Memorial Field Trial & Recreation Area (15 mi / 24.2 km)
  • Dizzy Gillespie Park (11.3 mi / 18.3 km)
  • Caston Park (11.5 mi / 18.5 km)
  • Little Park (17.5 mi / 28.2 km)

Frequently asked questions

How much does it cost to rent a vacation rental in Chesterfield?
The average price for a vacation rental in Chesterfield can vary depending on factors like length of stay, property type and season. Whether you're thinking about a sprawling villa with lots of bedrooms or a quaint cabin for you and your other half, just enter your dates of travel to view stays with unbeatable value.
How much does it cost to rent a beach house in Chesterfield?
Prices for beach houses in Chesterfield vary depending on the style and size of the property and time of year you're traveling. Just enter your travel dates into Vrbo and how many guests to view your options and prices. From there you can use our filter tool to tailor your search by ratings, amenities and more.
How old do you have to be to rent a vacation rental in Chesterfield?
It's advisable to check with the Chesterfield vacation home you're considering on Vrbo as age restrictions vary. However, it's generally 16, 18 or 21.
How long can I rent a vacation rental in Chesterfield for?
The amount of time you can rent a Chesterfield vacation rental for is up to the property. Just enter your dates of travel to browse available options offering longer term stays. They include all you need to make your extended vacation more enjoyable and convenient, like kitchens and air conditioning. Some vacation rentals may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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