Holiday Rentals in Chesterfield County

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Top cities in Chesterfield County

Check prices for these dates

Our top choices for Chesterfield County holiday rentals

1. 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.
The price is €212
includes taxes & fees
19 Nov - 20 Nov
Newly finished basement suite in Midlothian. Very clean and spacious.

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

Game Room + Yard: Updated House in Chester!
3.0 star property
Chester
The price is €312
includes taxes & fees
15 Nov - 16 Nov
Game Room + Yard: Updated House in Chester!

3. 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)
"The location is beautiful! Kristina was very prompt in answering my questions and very accommodating. Wonderful stay."
United States
Connie D.
The price is €242
includes taxes & fees
16 Nov - 17 Nov
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

4. 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.
The price is €207
includes taxes & fees
13 Nov - 14 Nov
Private bedroom and bath!

5. 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.
The price is €304
includes taxes & fees
15 Nov - 16 Nov
Game Room + Yard: Updated House in Chester!

6. 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.
The price is €393
includes taxes & fees
15 Nov - 16 Nov
Qualla Park

7. 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.
The price is €248
includes taxes & fees
30 Nov - 1 Dec
Charming 1-bedroom suite with WiFi and AC in Bon Air

8. Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience

Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience
Petersburg
9.0 out of 10, Wonderful, (6 reviews)
"Big yard."
United States
Michael O.
The price is €386
includes taxes & fees
21 Nov - 22 Nov
Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience

9. Midlothian 3 Bedroom getaway for up to 8 guests!

Midlothian 3 Bedroom getaway for up to 8 guests!
Midlothian
9.6 out of 10, Exceptional, (25 reviews)
"Great host and close to everything!"
United States
Brian V.
The price is €467
includes taxes & fees
16 Nov - 17 Nov
Midlothian 3 Bedroom getaway for up to 8 guests!

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

Serene 6-bedroom house with AC in charming Midlothian
Brandermill
The price is €776
includes taxes & fees
16 Nov - 17 Nov
Serene 6-bedroom house with AC in charming Midlothian

11. Historic Vincent House - Luxury 5BR Retreat Near Richmond, Virginia - Sleeps 12

Historic Vincent House - Luxury 5BR Retreat Near Richmond, Virginia - Sleeps 12
Midlothian
10.0 out of 10, Exceptional, (12 reviews)
"This vintage home was the perfect place for our stay. It was very clean, had everything we needed, and the location near the wedding venue couldn’t have been better."
United States
Sandy
Historic Vincent House - Luxury 5BR Retreat Near Richmond, Virginia - Sleeps 12

12. 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
The price is €250
includes taxes & fees
13 Nov - 14 Nov
MV GiaMaria

13. 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, (253 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.
The price is €187
includes taxes & fees
17 Nov - 18 Nov
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

14. 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.
The price is €187
includes taxes & fees
17 Nov - 18 Nov
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

15. Cozy Blackstone Getaway < 2 Mi to Downtown!

Cozy Blackstone Getaway < 2 Mi to Downtown!
3.0 star property
Blackstone
10.0 out of 10, Exceptional, (2 reviews)
"Clean, comfortable place for 2-4 people. 4 might be pushing it with one bath. Ate at The Brew House and Mitchell’s and both were quite good."
United States
Richard
Cozy Blackstone Getaway < 2 Mi to Downtown!

16. 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.
The price is €179
includes taxes & fees
25 Nov - 26 Nov
The Birdhouse - Cozy Cottage Retreat in Richmond

17. 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.
The price is €132
includes taxes & fees
7 Dec - 8 Dec
Nest & Rest | Private Studio | Free Parking

18. 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 traveller
The price is €55
includes taxes & fees
13 Nov - 14 Nov
2 Full Beds|Non-Smoking

19. Steel Magnolias Cozy Main Home in Amelia County

Steel Magnolias Cozy Main Home in Amelia County
Amelia Court House
9.8 out of 10, Exceptional, (16 reviews)
"What a wonderful place to stay in Amelia. We enjoyed this spot so much. Pristine cleanliness, everything you could image needing or wanting and an awesome space for enjoying hanging around the house with family. Can’t wait to stay here again in the future while we are visiting our son at HSC."
United States
Lori
The price is €249
includes taxes & fees
1 Dec - 2 Dec
Steel Magnolias Cozy Main Home in Amelia County

20. Cozy studio apartment in tranquil Richmond with heat and gym access

Cozy studio apartment in tranquil Richmond with heat and gym access
Downtown Richmond
8.8 out of 10, Excellent, (9 reviews)
"Clean environment. Great views. Very little parking flexibility but an enjoyable walk."
United States
Cailyn
The price is €75
includes taxes & fees
23 Nov - 24 Nov
Cozy studio apartment in tranquil Richmond with heat and gym access
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.

Find holiday rentals that suit your style

Find out more about Chesterfield County

Everything you need to know about Chesterfield County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield County holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield County holiday rentals we have selected for you start as low as €54 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield County rentals

At Expedia, we put the best Chesterfield County holiday 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 County 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 County holiday.

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 County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.