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

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chesterfield vacation rentals

A kitchen with a wooden island, stainless steel appliances, and a chandelier.

1. Qualla Park

Qualla Park
Chesterfield County
10.0 out of 10, Exceptional, (5 reviews)
"The home was beautiful and amazing! Host was amazing too! Highly recommend!"
United Kingdom
Shannon W.
$458 nightly
The price is $466
Oct 19 - Oct 20
Total with taxes and fees
Qualla Park
A rural landscape with a dirt path, grassy areas, and a building with a green roof.

2. 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.
$243 nightly
The price is $279
Oct 19 - Oct 20
Total with taxes and fees
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
A bedroom with a large bed, a chandelier, a window with curtains, and a painting on the wall.

3. Boutique 4 BR Stay/ 3 Kings/ Backyard/ Fireplace

Boutique 4 BR Stay/ 3 Kings/ Backyard/ Fireplace
Chesterfield
Boutique 4 BR Stay/ 3 Kings/ Backyard/ Fireplace
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

4. Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (9 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
Oct 18 - Oct 19
Total with taxes and fees
Cookie B
A marina with docked boats, a covered structure, and a forested hillside in the background.

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, (249 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.
$188 nightly
The price is $215
Oct 22 - Oct 23
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A calm lake with a dock and a small building, surrounded by trees.

6. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.2 out of 10, Wonderful, (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
Oct 18 - Oct 19
Total with taxes and fees
MV GiaMaria
A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

7. 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
Oct 18 - Oct 19
Total with taxes and fees
Game Room + Yard: Updated House in Chester!
A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

8. 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.
$293 nightly
The price is $337
Oct 18 - Oct 19
Total with taxes and fees
Game Room + Yard: Updated House in Chester!
A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

9. 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.
$197 nightly
The price is $227
Oct 26 - Oct 27
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.
A grand lobby with a large Christmas tree, marble columns, and a red carpeted floor.

10. 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.
$188 nightly
The price is $215
Oct 22 - Oct 23
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

11. 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.
$203 nightly
The price is $206
Oct 18 - Oct 19
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
A two-story house with a front deck, a small porch, and a backyard with a trampoline and a grill.

12. 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.
$203 nightly
The price is $234
Oct 18 - Oct 19
Total with taxes and fees
Private bedroom and bath!
A living room with a sectional sofa, a flat-screen TV, a ceiling fan, and a modern chandelier.

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.
$259 nightly
The price is $298
Oct 18 - Oct 19
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air
A room with a flat-screen TV mounted on the wall, a neon sign, a white cabinet with wine glasses, and a black cabinet with a white lamp.

14. The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6

The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6
Woodhaven
$341 nightly
The price is $389
Oct 19 - Oct 20
Total with taxes and fees
The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6
A corner building with large windows and a black awning.

15. Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown

Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown
Downtown Richmond
9.6 out of 10, Exceptional, (26 reviews)
"Great location, reasonable rates for the area, friendly helpful staff. Would stay here again."
United States
George L.
$152 nightly
The price is $174
Oct 19 - Oct 20
Total with taxes and fees
Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown
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.
$406 nightly
The price is $464
Oct 20 - Oct 21
Total with taxes and fees
Charming 3-bedroom townhome with WiFi in delightful Richmond
A modern kitchen with a central island, white cabinetry, and a large window with a view of greenery.

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

Serene 6-bedroom house with AC in charming Midlothian
Brandermill
$587 nightly
The price is $676
Oct 27 - Oct 28
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.

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

Private Garden Home w/ Large Fenced Yard + Gazebo
Broad Rock
10.0 out of 10, Exceptional, (5 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.
$334 nightly
The price is $382
Oct 22 - Oct 23
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
A room with a fireplace, a mirror above it, and two leather chairs.

19. Nest & Rest | Private Studio | Free Parking

Nest & Rest | Private Studio | Free Parking
Fan District
9.8 out of 10, Exceptional, (46 reviews)
"Host was gracious and responsive, and the location was amazing! "
United States
Kelly M.
Nest & Rest | Private Studio | Free Parking
A modern kitchen with a central island, stainless steel appliances, and bar stools.

20. The Studio@ Eanes Drug-Heart of the Historic District

The Studio@ Eanes Drug-Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (103 reviews)
"Great spot. Second time staying and another excellent experience."
United States
Nello D.
$169 nightly
The price is $193
Oct 18 - Oct 19
Total with taxes and fees
The Studio@ Eanes Drug-Heart of the Historic District
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 Jefferson Hotel

The Jefferson Hotel

10/10 Excellent
"Clean room; easy self park"
rich 1-night trip
Posted less than an hour ago
The Jefferson Hotel

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 $193 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.