151+ Private Villas and Holiday Rentals in Chesterfield County |
  1. USA
  2. Virginia
  3. Chesterfield County

Chesterfield County Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chesterfield County

Discover more than 151 vacation rentals available in Chesterfield County. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chesterfield County.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chesterfield County, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chesterfield County. On average, places to stay near Chesterfield County offer 850.83 ft², with nightly prices averaging US $272.

With Casai, finding and comparing holiday rentals in Chesterfield County is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Show more
Show less

Top Accommodation Types in Chesterfield County

Type Count
Vacation Homes 75
Holiday Apartments 21
Cottages 4
Villas 1

Use these Quick Filters to Find a Holiday Rental in Chesterfield County

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chesterfield County.

Weather in Chesterfield County, VA

View the weather forecast for Chesterfield County before booking your Chesterfield County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chesterfield County, VA

Casai offers a large selection of top attractions around Chesterfield County . Research things to do on your vacation before you visit Chesterfield County.


Virginia State University
Chesterfield Towne Center
Pocahontas State Park
Chippenham Hospital
Uptown Alley
Metro Richmond Zoo
Putt-Putt Fun Center
Iron Bridge Sports Park
Rockwood Park
Henricus Historical Park
The Lazy Daisy
Pocahontas State Park Museum
Castlewood
Robious Landing Park
King Pin Lanes
Oasis Sports Park
Stuffy Bear Factory
Chesterfield Historical Society of Virginia
Mid-Lothian Mines Park
Southside Speedway
Swift Creek Mill Theatre
Dutch Gap Conservation Area
Point of Rocks Park
Presquile National Wildlife Refuge
Magnolia Grange
Windy Hill Sports
Black Dog Paddle
Sweets & Treats
Parker's Battery Park
Rogers Stadium

Other Places to Stay in Chesterfield County, VA


Moseley 110 Properties
Dale 94 Properties
Chesterfield Court House 92 Properties
Ettrick 88 Properties
Chester 49 Properties
Bermuda 49 Properties
Hampton Park 43 Properties
Clover Hill 37 Properties
Midlothian 36 Properties
Brandermill 32 Properties
Chesterfield 28 Properties
Woodvale 24 Properties

Frequently Asked Questions About Chesterfield County?

What are the top holiday rentals in Chesterfield County?

With numerous options available in Chesterfield County, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chesterfield County:

How many holiday rentals have private pools in Chesterfield County?

Discover a selection of holiday rentals with private pools near Chesterfield County with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Chesterfield County are best for families?

If you're searching for a family-friendly holiday home in Chesterfield County, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chesterfield County:

How many Casai.com holiday rentals are available in Chesterfield County?

As of 2026, Casai boasts over 151 properties listed in the Chesterfield County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chesterfield County.


People Also Ask

There are 151 Chesterfield County, VA Holiday Rentals

Recently Booked Holiday Rentals in Chesterfield County