Chesterfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Chesterfield vacation rentals

Property grounds

Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
Chesterfield
10.0 out of 10, Exceptional, (5 reviews)
"The location is beautiful! Kristina was very prompt in answering my questions and very accommodating. Wonderful stay."
United States
Connie D.
The price is ￥14,477
￥39,393 total
includes taxes & fees
May 28 - May 29
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
3 bedrooms, desk, iron/ironing board, free WiFi

Qualla Park

Qualla Park
Chesterfield County
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in. House is wonderful. These hosts have thought of everything!!"
United States
Diane L.
The price is ￥28,667
￥69,868 total
includes taxes & fees
Jun 1 - Jun 2
Qualla Park
Lobby

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Richmond
9.6 out of 10, Exceptional, (117 reviews)
"Very nice stay! Awesome host and quiet neighborhood! Thank you!"
United States
Wes E.
The price is ￥18,315
￥33,668 total
includes taxes & fees
May 31 - Jun 1
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Marina

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Richmond
9.4 out of 10, Exceptional, (236 reviews)
"Beautiful setting and comfortable accommodations. "
United States
deirdre b.
The price is ￥18,315
￥33,668 total
includes taxes & fees
May 31 - Jun 1
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Front of property

Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (8 reviews)
"Capt. Ron has a charming, welcoming, and delightful alternative to a standard hotel room on offer here. Super fun!"
United States
Robert
The price is ￥34,838
￥47,679 total
includes taxes & fees
May 28 - May 29
Cookie B
Fridge, microwave, oven, stovetop

Luxury Stay! 10 min away from Fort Lee.

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.4 out of 10, Very Good, (17 reviews)
"Very nice home. "
United States
Shannon C.
The price is ￥23,650
￥66,086 total
includes taxes & fees
Jun 1 - Jun 2
Luxury Stay! 10 min away from Fort Lee.
1 bedroom, in-room safe, free WiFi, bed sheets

Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (23 reviews)
"Enjoyed my stay a lot! The property definitely has charm, the experience was very laid back. "
United States
Grace
The price is ￥11,323
￥20,219 total
includes taxes & fees
Jun 1 - Jun 2
Magnolias, a chill out place.
1 bedroom, free WiFi, bed sheets

The Farmhouse Retreat

The Farmhouse Retreat
Mechanicsville
10.0 out of 10, Exceptional, (4 reviews)
"Nice place in the country. Tyler is an excellent host. "
United States
Tom C.
The price is ￥14,174
￥25,478 total
includes taxes & fees
May 28 - May 29
The Farmhouse Retreat
Dining

Carytown cozy nest private room Fenced Yard

Carytown cozy nest private room Fenced Yard
Carytown
9.8 out of 10, Exceptional, (28 reviews)
"Everything was smooth and as promised. We recommend this spot!"
United States
Stefin P.
The price is ￥11,945
￥23,069 total
includes taxes & fees
Jun 3 - Jun 4
Carytown cozy nest private room Fenced Yard
Living area

The SageBrush Cottage

The SageBrush Cottage
North Highland Park
The price is ￥20,067
￥51,145 total
includes taxes & fees
Jun 1 - Jun 2
The SageBrush Cottage
Terrace/patio

Studio Nest/2Queen beds/2TVs museums/free parking

Studio Nest/2Queen beds/2TVs museums/free parking
Fan District
9.8 out of 10, Exceptional, (65 reviews)
"Location, easy check in, very communicative host. "
United States
Sarah T.
The price is ￥16,563
￥30,019 total
includes taxes & fees
Jun 8 - Jun 9
Studio Nest/2Queen beds/2TVs museums/free parking
Smart TV, fireplace

The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (1 review)
"The most beautifully finished cottage! Host very responsive!! Loved it."
United States
Stephanie S.
The price is ￥14,297
￥31,405 total
includes taxes & fees
May 30 - May 31
The Birdhouse - Cozy Cottage Retreat in Richmond
Terrace/patio

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Northern Barton Heights
9.6 out of 10, Exceptional, (16 reviews)
"Great kitchen and comfy beds."
United States
Christina O.
The price is ￥17,041
￥64,066 total
includes taxes & fees
Jun 7 - Jun 8
Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Outdoor dining

Colorful private guesthouse in charming Richmond with Parking

Colorful private guesthouse in charming Richmond with Parking
Northern Barton Heights
10.0 out of 10, Exceptional, (5 reviews)
"Such a fun place to stay! Room is nicely decorated. Easy check in/check out. Never stayed in this part of RVA before. We will definitely stay here again!"
United States
Teresa M.
The price is ￥16,722
￥34,578 total
includes taxes & fees
Jun 2 - Jun 3
Colorful private guesthouse in charming Richmond with Parking
Fridge, microwave, oven, stovetop

The Studio@ Eanes Drug

The Studio@ Eanes Drug
Church Hill
10.0 out of 10, Exceptional, (78 reviews)
"Room was wonderful, very clean & cozy. Great location!"
United States
Kirk
The price is ￥22,296
￥29,119 total
includes taxes & fees
May 31 - Jun 1
The Studio@ Eanes Drug
Interior

Carytown Gem: Family-Friendly Apartment with Yard

Carytown Gem: Family-Friendly Apartment with Yard
Carytown
9.8 out of 10, Exceptional, (75 reviews)
"Location was great. Very walkable town"
United States
patricia h.
The price is ￥17,837
￥36,641 total
includes taxes & fees
Jun 7 - Jun 8
Carytown Gem: Family-Friendly Apartment with Yard
Interior

Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs

Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
Byrd Park
9.0 out of 10, Wonderful, (17 reviews)
"Very nice staff"
United States
Jessica
The price is ￥18,793
￥42,663 total
includes taxes & fees
Jun 8 - Jun 9
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
Interior

Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Richmond
8.6 out of 10, Excellent, (34 reviews)
"Was I great place to stay! Very responsive and gave all the info you need to make the trip and stay easy! "
United States
Dillon D.
The price is ￥18,227
￥51,579 total
includes taxes & fees
Jun 1 - Jun 2
Downtown Living in Richmond's Amazing Shockoe Bottom
TV

Modern Apartment- Walk to Convention Center- Deck- Off-Street Parking

Modern Apartment- Walk to Convention Center- Deck- Off-Street Parking
Downtown Richmond
10.0 out of 10, Exceptional, (3 reviews)
"Alex was super communicative and the apartment was exactly as advertised. Would absolutely recommend!"
United States
Nicholas S.
The price is ￥12,438
￥46,794 total
includes taxes & fees
May 28 - May 29
Modern Apartment- Walk to Convention Center- Deck- Off-Street Parking
TV

Lovely 2 Bedroom in the Heart of The Fan

Lovely 2 Bedroom in the Heart of The Fan
Fan District
9.2 out of 10, Wonderful, (84 reviews)
"Easy check in and a pleasant quick stay "
United States
Megan M.
The price is ￥18,227
￥56,346 total
includes taxes & fees
May 28 - May 29
Lovely 2 Bedroom in the Heart of The Fan
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Microtel Inn & Suites by Wyndham Richmond Airport

Microtel Inn & Suites by Wyndham Richmond Airport

8/10 Good
"Recently remodeled great stay in the budget price range. Breakfast was very minimal so don’t expect much there but still clean and a great value close to airport and shopping."
Charles 1-night trip
Posted 3 hours ago
Microtel Inn & Suites by Wyndham Richmond Airport

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 give you a choice of vacation rentals close to popular local attractions in Chesterfield, or you can choose a more secluded option if you're looking for relaxation. Chesterfield is known for its shopping and golf courses. Make sure you have time to check out the parks and museums during your trip.

What are some of the best vacation rentals that Chesterfield has to offer?

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!: This vacation home rental outside of Chesterfield has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chesterfield?

Expedia has 7 vacation rentals for your stay in Chesterfield.

What can I see and do in Chesterfield?

While exploring the area, visit family-friendly sights like Iron Bridge Sports Park, or get outside and enjoy nature at Appomattox River. Pocahontas State Park and Magnolia Grange are other places to visit while you're in town.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Chesterfield. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a small group gathering.