Chesterfield Vacation Rentals

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In two weeks
Oct 24 - Oct 26
In two months
Dec 5 - Dec 7
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Jan 30 - Feb 1

Vacation Rentals in Chesterfield

Cozy Waterfront Retreat at McMichael Farms
Dining

Cozy Waterfront Retreat at McMichael Farms

2.0 star property
10.0 out of 10, Exceptional, (11)
"we loved the property, it so quiet and tranquil and a great get away. We loved all the details of the home, the morning view over the pond was amazing while drinking our coffee. "
Cozy Waterfront Retreat at McMichael Farms
Bright Converted Schoolhouse in Chesterfield!
House (1 Bedroom) | Interior

Bright Converted Schoolhouse in Chesterfield!

3.0 star property
Bright Converted Schoolhouse in Chesterfield!
“CAROLINA” tiny house with Pond View
Smart TV, fireplace

“CAROLINA” tiny house with Pond View

10.0 out of 10, Exceptional, (3)
"Had a very pleasant stay. Beautiful and peaceful place to stay."
“CAROLINA” tiny house with Pond View
Quiet lakefront condo with the best views on Prestwood lake.
Property grounds

Quiet lakefront condo with the best views on Prestwood lake.

Quiet lakefront condo with the best views on Prestwood lake.
Country retreat home away from the hustle and bustle of city life.
Property grounds

Country retreat home away from the hustle and bustle of city life.

9.4 out of 10, Exceptional, (19)
"Great location and proximity to the university!! We would definitely stay again "
The price is ￥20,588
￥51,014 total
includes taxes & fees
Oct 21 - Oct 22
Country retreat home away from the hustle and bustle of city life.
Great property for contract healthcare workers!
Exterior

Great property for contract healthcare workers!

10.0 out of 10, Exceptional, (32)
"Very clean and comfortable place to stay "
The price is ￥22,542
￥32,194 total
includes taxes & fees
Oct 29 - Oct 30
Great property for contract healthcare workers!
Cozy cabin on 16.5 acres with a stocked fishing pond. Close to Charlotte.
Fridge, microwave, oven, stovetop

Cozy cabin on 16.5 acres with a stocked fishing pond. Close to Charlotte.

10.0 out of 10, Exceptional, (23)
"It was a great place and better than advertised"
Cozy cabin on 16.5 acres with a stocked fishing pond. Close to Charlotte.
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet
Property grounds

The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet

10.0 out of 10, Exceptional, (14)
"Myself and my son-in-law stayed here overnight on our way to the US Open at Pinehurst. Very Clean and neat place to stay."
The price is ￥8,115
￥12,792 total
includes taxes & fees
Oct 12 - Oct 13
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet
Cozy Blue Cottage 2BR/1BA
Exterior

Cozy Blue Cottage 2BR/1BA

8.8 out of 10, Excellent, (6)
"Enjoyed my time in Hartsville with family "
The price is ￥15,029
￥32,985 total
includes taxes & fees
Oct 22 - Oct 23
Cozy Blue Cottage 2BR/1BA
Skipper 3- Charming 1-bedroom apartment in Rockingham with WiFi, AC
Private kitchen

Skipper 3- Charming 1-bedroom apartment in Rockingham with WiFi, AC

10.0 out of 10, Exceptional, (1)
"Perfect location, everything needed was close by. We were in town to catch some races at the Dragway. The apartment was freshly furnished and very clean. Really enjoyed our stay."
The price is ￥12,022
￥21,180 total
includes taxes & fees
Oct 14 - Oct 15
Skipper 3- Charming 1-bedroom apartment in Rockingham with WiFi, AC
In 1840 Burn Cottage
Property grounds

In 1840 Burn Cottage

9.8 out of 10, Exceptional, (33)
"Nice historic house provided authentic late-1800s three night stay. Enjoyed our stay."
The price is ￥16,230
￥30,795 total
includes taxes & fees
Oct 9 - Oct 10
In 1840 Burn Cottage
Lakeside 2-bedroom RV in charming Hartsville with AC, WiFi
Interior

Lakeside 2-bedroom RV in charming Hartsville with AC, WiFi

8.0 out of 10, Very Good, (1)
"The stay was fine , with no problems."
The price is ￥10,247
￥22,753 total
includes taxes & fees
Oct 12 - Oct 13
Lakeside 2-bedroom RV in charming Hartsville with AC, WiFi
Private Nature Oriented Campground
Property grounds

Private Nature Oriented Campground

The price is ￥6,763
￥12,708 total
includes taxes & fees
Oct 9 - Oct 10
Private Nature Oriented Campground
Lakeside Living
Terrace/patio

Lakeside Living

8.8 out of 10, Excellent, (3)
"James has been amazing! This place turned into an extended stay for one of our guys at work and he loved it! It met all our expectations. James was always available, responded to messages quickly, and just went above and beyond to accommodate our needs. Great guy and great place! "
Lakeside Living
Gorgeous, Southern Home in Beautiful Cheraw
Fridge, microwave, oven, stovetop

Gorgeous, Southern Home in Beautiful Cheraw

10.0 out of 10, Exceptional, (17)
"We loved all the rooms and they were roomy and the out door area is a must see also hospitality was great."
Gorgeous, Southern Home in Beautiful Cheraw
Charming 3-bedroom house with AC and WiFi in serene Cheraw
Exterior detail

Charming 3-bedroom house with AC and WiFi in serene Cheraw

10.0 out of 10, Exceptional, (2)
"Wonderful place to relax. Quiet location with access to a variety of restaurants and shops. A short drive to Darlington where we spent the weekend for the races. "
Charming 3-bedroom house with AC and WiFi in serene Cheraw
Central Wadesboro Home: Walk to Downtown Shops!
House (3 Bedrooms) | Interior

Central Wadesboro Home: Walk to Downtown Shops!

3.0 star property
8.0 out of 10, Very Good, (1)
Central Wadesboro Home: Walk to Downtown Shops!
Charming 3-bedroom house with AC and WiFi in peaceful Rockingham
3 bedrooms, WiFi, bed sheets

Charming 3-bedroom house with AC and WiFi in peaceful Rockingham

2.0 star property
Charming 3-bedroom house with AC and WiFi in peaceful Rockingham
Charming 2-bedroom townhome in quaint Hamlet with WiFi, AC
Fridge, oven, stovetop, coffee/tea maker

Charming 2-bedroom townhome in quaint Hamlet with WiFi, AC

Charming 2-bedroom townhome in quaint Hamlet with WiFi, AC
Skipper 4 - Lovely 1-bedroom apartment in welcoming Rockingham with WiFi, AC
Fridge, microwave, oven, stovetop

Skipper 4 - Lovely 1-bedroom apartment in welcoming Rockingham with WiFi, AC

Skipper 4 - Lovely 1-bedroom apartment in welcoming Rockingham with WiFi, AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterfield Hotel Reviews

The Mantissa Hotel

The Mantissa Hotel

10/10 Excellent
"Very nice spacious rooms friendly staff"
Duane 3-night trip
Posted 2 days ago
The Mantissa Hotel

Find out more about Chesterfield

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find a vacation rental in Chesterfield?

Yes, we have vacation rentals near the most popular sights in Chesterfield, or you can select a more secluded option if you want a relaxing place to stay.

What's the top vacation rental that Chesterfield has to offer?

“CAROLINA” tiny house with Pond View: Visitors like this Chesterfield vacation home rental. It offers a fireplace, a private yard, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the hot tub in this rental home to help you unwind.

How many vacation rentals are there in Chesterfield?

Choose from 4 Expedia vacation rentals in Chesterfield for a memorable vacation.

What can I see and do in Chesterfield?

Explore the area and family-friendly sights such as Granny Hollow Pottery and Fancy Crafts, or get out into nature at a spot like Cheraw State Park. Northeastern Technical College and Cheraw State Park Golf Course are a couple of places you'll find in the larger area.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned accommodations you can reserve for a couple days or more in Chesterfield. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.