Best Vacation Homes in Chesterfield
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $89/Night
For 7 Nights US $626
96.88 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $90/Night
For 7 Nights US $630
US $115/Night
For 7 Nights US $806
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $74/Night
For 7 Nights US $516
882.64 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Parking
- Internet
US $259/Night
For 7 Nights US $1,811
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $72/Night
For 7 Nights US $501
880 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $216/Night
For 7 Nights US $1,512
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $354/Night
For 7 Nights US $2,475
Chesterfield Luxury Rentals
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $344/Night
For 7 Nights US $2,411
US $187/Night
For 7 Nights US $1,311
176.71 ft²
12 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $136/Night
For 7 Nights US $950
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $128/Night
For 7 Nights US $894
368.12 ft²
10 Bathrooms
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
US $123/Night
For 7 Nights US $862
247.57 ft²
1 Bathroom
Free Cancellation
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $122/Night
For 7 Nights US $853
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $106/Night
For 7 Nights US $742
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $104/Night
For 7 Nights US $730
Chesterfield Pet Friendly Vacation Rentals
889 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $147/Night
For 7 Nights US $1,028
204.51 ft²
4 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $68/Night
For 7 Nights US $477
US $80/Night
For 7 Nights US $562
US $51/Night
For 7 Nights US $357
161.45 ft²
2 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Pet Friendly
- Parking
US $76/Night
For 7 Nights US $531
Chesterfield Large Vacation Homes
6 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $314/Night
For 7 Nights US $2,195
Why Choose Rent By Owner for your Chesterfield Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Chesterfield
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, allowing you to enjoy the region’s unique climate and local events while ensuring your booking in Chesterfield, Indiana, USA aligns with your ideal vacation plans.
Peak Season Highlights
Late Spring to Early Summer (May to June)
This is when the weather warms up, making it ideal for enjoying the outdoor scenery and local activities in the area.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Fall (September to October)
During this period, the region offers stunning autumn foliage, providing picturesque views perfect for outdoor exploration.
Average Temperature Daytime: 68-78°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
The winter months see fewer visitors, offering a quiet escape with cooler temperatures suitable for cozy stays in your rental property.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Early Spring (March to April)
Before the peak springtime crowds arrive, this season provides a peaceful environment to experience the area's early blooms and emerging nature.
Average Temperature Daytime: 50-60°F - Nighttime: 35-45°F
Weekly Weather Forecast for Chesterfield
How to Book Your Chesterfield 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 Chesterfield
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 outdoor dining areas perfect for meals al fresco during your stay in the region.
- Relax by private or shared fire pits, ideal for cozy evenings under the stars.
- Make use of scenic patios or decks that offer picturesque views of the surrounding countryside.
- Take advantage of landscaped gardens and lawn spaces for outdoor recreation or relaxation.
- Benefit from access to nearby walking trails or nature paths embedded within the outdoor space.
- Utilize shared or private outdoor swimming pools to stay cool during warmer months.
- Discover outdoor sports amenities such as basketball courts or volleyball courts available at some properties.
Top Attractions Around Chesterfield
What attractions are nearby?
Discover a variety of outdoor activities, local parks, and scenic trails just minutes from your chosen vacation rentals here, offering you the perfect opportunity to explore the natural beauty and recreational options that make this destination a memorable part of your Indiana experience.
Family Activities
- Chesterfield Community Park: Enjoy a family picnic, playground, and outdoor activities at this scenic park within the area.
- Harrison County Fairgrounds: Attend seasonal fairs and community events that offer fun for all ages in this family-friendly destination.
- Local Nature Trails: Explore nearby hiking and biking trails, perfect for outdoor adventures with children and nature enthusiasts.
- Historic Sites and Museums: Discover local history through engaging exhibits and guided tours ideal for family educational outings in the region.
Adult Activities
- Exploring the local golf courses: You can enjoy a relaxing day on the scenic fairways that showcase the area's lush landscapes and offer a great way to unwind.
- Visiting nearby parks and nature reserves: Spend your time outdoors by discovering the region's beautiful parks, perfect for walking, picnicking, or simply enjoying nature.
- Trying regional dining experiences: Sample the local cuisine at charming restaurants around the area that highlight the region’s culinary traditions.
- Attending community events and festivals: Immerse yourself in local culture by participating in seasonal events and festivals held throughout here, offering unique entertainment and craft opportunities.
Chesterfield Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the event calendar to align your stay with local festivals or gatherings, enhancing your experience in this charming destination.
- Explore Nearby Attractions: Utilize your vacation rentals as a comfortable base to discover nearby parks and cultural sites that showcase the region's unique charm.
- Choose Strategic Accommodation Locations: Select a rental that offers easy access to major roads and amenities, making it more convenient to explore all that this area has to offer.
- Engage with Local Resources: Seek recommendations from your host or online guides to uncover hidden gems and authentic dining options around the region.
Transportation Options
- Personal Vehicles: Renting or driving your own car offers the most flexibility for exploring the region surrounding Chesterfield, Indiana, with easy access to local attractions and nearby cities.
- Public Transit: Local bus services provide a convenient transportation option for getting around here without the need for personal vehicle ownership.
- Taxi and Rideshare Services: Rideshare companies and taxis are reliable choices for quick trips within the area, ensuring you can reach your destination comfortably and on time.
- Rental Bicycles: Biking is an eco-friendly and enjoyable way to explore here at your own pace, especially on designated bike paths and scenic routes in this destination.
Local Customs Options
- Local Festivals and Events: You can experience the area's vibrant community spirit through traditional festivals that celebrate its history and culture, often attracting visitors from nearby regions.
- Traditional Southern Hospitality: Expect warm welcomes and friendly interactions rooted in local customs when engaging with residents here, reflecting the region’s considerate hospitality.
- Regional Cuisine and Food Traditions: Enjoy the authentic flavors of locally inspired dishes that highlight the region's culinary heritage, available at community gatherings and eateries.
- Historic Preservation Practices: Discover how the area values its history by observing preservation efforts that maintain old architecture and landmarks, giving you a glimpse into its past.
Frequently Asked Questions About Chesterfield?
1. What are the top vacation rentals in Chesterfield?
There are a lot of options in Chesterfield. If you plan on staying in the Chesterfield area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chesterfield:
- Modern 1 bedroom 1 bath apartment
- Furnished 2ND FLOOR 2-bedroom Downtown Anderson IN
- Lux 1 bed/1 bath unit ideal for traveling professional
- Spacious Modern 1bd/1bth Mins Downtown Anderson
- 7 Mi to Mounds State Park: Indiana Home w/Porch!
- The Winner’s Circle - Pool, Hot Tub, Next to Harrah’s Casino
- Best Western Plus Anderson
- Fairfield Inn & Suites by Marriott Anderson
- Best Western Plus Anderson
- Tru By Hilton Anderson
2. Which vacation homes in Chesterfield are best for families?
If you are looking for a family-friendly vacation home in Chesterfield, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chesterfield:
3. How many Rentbyowner vacation rentals are available in Chesterfield?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 47 in the Chesterfield 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 Chesterfield.
4. What is the cancellation policy for vacation rentals in Chesterfield, Indiana?
Cancellation policies vary depending on the property listing. To ensure you understand the specific terms, please review the cancellation details provided in the rental listing or contact the property owner directly before booking.
5. How do I secure a reservation at a vacation rental near Chesterfield, Indiana?
Reservations are typically secured through the booking platform by submitting your details and payment information. For specific instructions or assistance, refer to the property's listing or reach out to the host directly.
6. Are there any house rules I should be aware of during my stay?
House rules differ by property and are outlined in each listing. It’s recommended to read these carefully before booking and contact the host if you have any questions regarding specific regulations or expectations.
7. Is there a minimum stay requirement for vacation rentals here?
Minimum stay requirements can vary based on the property and season. Check the individual listing details for this destination to confirm the duration needed to make a reservation.
8. What amenities are typically included in vacation rentals near Chesterfield, Indiana?
Amenities offered differ depending on the property, but common features include kitchens, Wi-Fi, parking, and outdoor spaces. Review each listing for a detailed list of what’s included during your stay in the region.
Chesterfield Top Rated Vacation Rentals
US $104/Night
For 7 Nights US $726
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $75/Night
For 7 Nights US $526
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $104/Night
For 7 Nights US $729
US $93/Night
For 7 Nights US $653
204.51 ft²
1 Bathroom
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
US $75/Night
For 7 Nights US $525
US $71/Night
For 7 Nights US $494
US $104/Night
For 7 Nights US $728
