Two cannons in a grassy field with trees and a fence in the background.

Chesterfield Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chesterfield vacation rentals

A rural landscape with a pond, grassy fields, and trees under a cloudy sky.

1. 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, (7 reviews)
"Quiet and Cozy. Beautiful scenery, great walking trails. Host was extra accomdating with check-in and out process. Would definitely visit again "
United States
G H.
$221 nightly
The price is $254
Nov 11 - Nov 12
Total with taxes and fees
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
A kitchen with a wooden island, stainless steel appliances, and a chandelier.

2. Qualla Park

Qualla Park
Chesterfield County
10.0 out of 10, Exceptional, (7 reviews)
"The home was beautiful and amazing! Host was amazing too! Highly recommend!"
United Kingdom
Shannon W.
$422 nightly
The price is $424
Nov 8 - Nov 9
Total with taxes and fees
Qualla Park
A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

3. Newly finished basement suite in Midlothian. Very clean and spacious.

Newly finished basement suite in Midlothian. Very clean and spacious.
Midlothian
10.0 out of 10, Exceptional, (6 reviews)
"Cute place. Very spacious and clean. Great communication. Would definitely stay again. Thank you!"
United States
Jeannie C.
$200 nightly
The price is $230
Nov 15 - Nov 16
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.
A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

4. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
Chester
9.0 out of 10, Wonderful, (4 reviews)
"Great stay. Super clean! Great communication with host. 30 mins from Richmond VA, great for exploring surrounding areas!"
United States
Akia S.
$294 nightly
The price is $338
Nov 15 - Nov 16
Total with taxes and fees
Game Room + Yard: Updated House in Chester!
A compact living area with a blue sofa, a purple armchair, and a small table with a checkered edge.

5. 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, (251 reviews)
"We had a great stay! Perfect get away for our anniversary. It had everything we needed and was super quiet with a great view. Thank you Captain Ron, for an amazing experience "
United States
Allison K.
$178 nightly
The price is $203
Nov 8 - Nov 9
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

6. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
3.0 star property
Chester
$304 nightly
The price is $346
Nov 15 - Nov 16
Total with taxes and fees
Game Room + Yard: Updated House in Chester!
A cozy living room with a television, a fireplace, a Coca-Cola branded stool, and a patterned rug.

7. 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, (126 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
$178 nightly
The price is $203
Nov 8 - Nov 9
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A two-story house with a front deck, a small porch, and a backyard with a trampoline and a grill.

8. Private bedroom and bath!

Private bedroom and bath!
Midlothian
6.0 out of 10, (2 reviews)
"We had a lacrosse tournament at River city sports plex. This was perfect location to stay for us. Friendly and amazing combination with host. Extremely pleased with our stay"
United States
Ridge W.
$194 nightly
The price is $223
Nov 7 - Nov 8
Total with taxes and fees
Private bedroom and bath!
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

9. The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (6 reviews)
"The BirdHouse is such a comfortable place. We loved the uniqueness and the little touches that mean alot on the road. We hope to stay again sometime."
United States
paula S.
$196 nightly
The price is $198
Nov 15 - Nov 16
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
A hotel room with a large bed, a window with a view of boats, a lamp, and framed pictures on the wall.

10. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.4 out of 10, Exceptional, (16 reviews)
"So much fun!! Excellent host! Very informative. Loved the privacy and being on the water. The bed was super comfortable and the fireplace (electric) kept us warm and cozy. It was such a unique thing to do and we will be back!"
United States
Jane
$243 nightly
The price is $277
Nov 7 - Nov 8
Total with taxes and fees
MV GiaMaria
A boat with a cabin, a small deck area with a ramp, and a docked boat in the background.

11. Cookie B

Cookie B
3.0 star property
Richmond
9.2 out of 10, Wonderful, (10 reviews)
"Was fantastic. Watching the sunrise was so memorable, captain ron was so friendly and stayed in communication well. will visit again. "
United States
Reshelle
$263 nightly
The price is $299
Nov 7 - Nov 8
Total with taxes and fees
Cookie B
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

12. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Petersburg VA
10.0 out of 10, Exceptional, (4 reviews)
"Clean rooms with quick service!"
United States
Anonymous traveler
$69 nightly
The price is $76
Nov 9 - Nov 10
Total with taxes and fees
2 Queen Beds | Non-Smoking, Micfridge
A modern living room with a sofa set, a coffee table, and a TV.

13. Charming 1-bedroom suite with WiFi and AC in Bon Air

Charming 1-bedroom suite with WiFi and AC in Bon Air
Bon Air
8.8 out of 10, Excellent, (11 reviews)
"It was a nice stay the host was prompt and answered any questions or concerns right away, she was very polite and helpful to me and family "
United States
Jessica H.
$235 nightly
The price is $271
Nov 9 - Nov 10
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air
A bedroom with a bed, a TV, and built-in shelving with decorative items.

14. Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (25 reviews)
"Would stay again!"
United States
Amir D.
$97 nightly
The price is $111
Nov 9 - Nov 10
Total with taxes and fees
Magnolias, a chill out place.
A living room with a fireplace, two grey sofas with yellow pillows, a flat-screen TV above the fireplace, and a large plant to the left.

15. Stylish 1BR Apt w/ King Bed, Free Parking & 1.5 Baths

Stylish 1BR Apt w/ King Bed, Free Parking & 1.5 Baths
Fan District
9.8 out of 10, Exceptional, (65 reviews)
"Great place! "
United States
Brent W.
$140 nightly
The price is $155
Nov 9 - Nov 10
Total with taxes and fees
Stylish 1BR Apt w/ King Bed, Free Parking & 1.5 Baths
A living room with a beige sofa, a round black coffee table, a large window, and a painting of a tree.

16. Charming 3-bedroom townhome with WiFi in delightful Richmond

Charming 3-bedroom townhome with WiFi in delightful Richmond
Jahnke
10.0 out of 10, Exceptional, (8 reviews)
"Check-in was simple, good communication, property very much as described/depicted in the listing. Perfect location for our needs. "
United States
Mary C.
$386 nightly
The price is $441
Nov 9 - Nov 10
Total with taxes and fees
Charming 3-bedroom townhome with WiFi in delightful Richmond
A room with a sofa, a coffee table, a dining table with chairs, a window with a 'Thank You' sign, and a view of trees.

17. 2 Full Beds|Non-Smoking

2 Full Beds|Non-Smoking
Petersburg VA
10.0 out of 10, Exceptional, (81 reviews)
"Appreciated the cozy lounge area, made relaxing after a long day easy."
United States
Anonymous traveler
$54 nightly
The price is $61
Nov 7 - Nov 8
Total with taxes and fees
2 Full Beds|Non-Smoking
A modern living room with a sofa, a dining area with a round table, and a kitchen with built-in appliances.

18. Serene 6-bedroom house with AC in charming Midlothian

Serene 6-bedroom house with AC in charming Midlothian
Brandermill
$711 nightly
The price is $818
Nov 10 - Nov 11
Total with taxes and fees
Serene 6-bedroom house with AC in charming Midlothian
A wooden gazebo with a bench and string lights, surrounded by trees.

19. Private Garden Home w/ Large Fenced Yard + Gazebo

Private Garden Home w/ Large Fenced Yard + Gazebo
Broad Rock
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay here for two nights! The beds were extremely comfortable and it was quiet and peaceful sleeping there both nights. We enjoyed the backyard very much - both our pets and kids. My son thought the gazebo with twinkle lights out back was so magical. :) We appreciate the cleanliness of the place and would only have appreciated a little space with maybe kids’ books, puzzles, or blocks or something. My young kiddos go crazy for those things when we stay at vacation rentals and it...
United States
Stacie C.
$331 nightly
The price is $378
Nov 8 - Nov 9
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

20. Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite

Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite
Ettrick
10.0 out of 10, Exceptional, (22 reviews)
"The property was exactly as described. Everything we needed was on site. The owner communicated check-in details the day before our arrival date so there was no guesswork. This was our first VRBO experience and it was great. We visit the area twice a year, and we will be staying here again next spring."
United States
john
$434 nightly
The price is $500
Nov 8 - Nov 9
Total with taxes and fees
Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite
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

Linden Row Inn

Linden Row Inn

8/10 Good
"We enjoyed our stay at historic Linden Row. Originally built in the 1800’s and restored to period, you’ll find high ceilings, original wood floors and period chandeliers. We were celebrating our 25th so splurged and rented a two room suite. The hotel is charming but lacks the luxury you might find spending the same amount elsewhere. Parking is off site but close to the hotel. Location is centrally located. The floors in our suite looked like they hadn’t been vacuumed in awhile with dust visable beneath desk and cabinets. We made note of our anniversary at time of booking, and on two other occasions at the front desk, but no effort was made to honor our special day until we wrote to guest services. They responded apologetically and provided some special gifts. Apparently the person who provides special guest services was out of town. After reaching out four times at least they came around but having to speak out so many times and falling upon deaf ears left us thinking we should have booked elsewhere. Despite this huge oversight, we would return again."
Victoria 4-night trip
Posted 2 hours ago
Linden Row Inn

Find out more about Chesterfield

Everything you need to know about Chesterfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $81 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Spacious 4-bedroom house in awesome Midlothian with AC: This vacation home rental outside of Chesterfield offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals are there in Chesterfield?

Expedia has 6 vacation rentals for your stay in Chesterfield.

What can I see and do in Chesterfield?

Appomattox River and Swift Creek Reservoir are a couple of lovely local spots to get outside and enjoy nature. Pocahontas State Park and Castlewood 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.