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

Holiday Homes in Chesterfield

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chesterfield holiday homes

1. 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 €415
includes taxes & fees
6 Dec - 7 Dec
Qualla Park

2. 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 €210
includes taxes & fees
18 Nov - 19 Nov
Newly finished basement suite in Midlothian. Very clean and spacious.

3. 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!

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 €205
includes taxes & fees
13 Nov - 14 Nov
Private bedroom and bath!

5. 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
8.0 out of 10, Very good, (1 review)
"It was clean and nicely Renovated. It was clear, that they have put in work to improve the house. The showers could use a user manual."
United States
Lisa J.
The price is €328
includes taxes & fees
15 Nov - 16 Nov
The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6

6. 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.
The price is €328
includes taxes & fees
18 Nov - 19 Nov
Private Garden Home w/ Large Fenced Yard + Gazebo

7. River City Modern Retreat

River City Modern Retreat
Manchester
The price is €220
includes taxes & fees
16 Nov - 17 Nov
River City Modern Retreat

8. Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Downtown Richmond
9.8 out of 10, Exceptional, (93 reviews)
"Just a great space to stay very comfortable and the location is awesome - many nearby clubs bars and places to eat! Have stayed 4 times and one of my favorite places to stay anywhere"
United States
rob
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

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

Serene 6-bedroom house with AC in charming Midlothian
Brandermill
The price is €763
includes taxes & fees
17 Nov - 18 Nov
Serene 6-bedroom house with AC in charming Midlothian

10. 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 €246
includes taxes & fees
30 Nov - 1 Dec
Charming 1-bedroom suite with WiFi and AC in Bon Air

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

Charming 3-bedroom townhome with WiFi in delightful Richmond
Jahnke
9.8 out of 10, Exceptional, (9 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.
The price is €401
includes taxes & fees
15 Nov - 16 Nov
Charming 3-bedroom townhome with WiFi in delightful Richmond

12. Sweet Vine Of MIne

Sweet Vine Of MIne
Fan District
The price is €229
includes taxes & fees
22 Nov - 23 Nov
Sweet Vine Of MIne

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

Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience
Petersburg
8.8 out of 10, Excellent, (5 reviews)
"Big yard."
United States
Michael O.
Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience

14. VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms

VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
Randolph
9.8 out of 10, Exceptional, (149 reviews)
"Great place in Richmond!"
United States
Cindy S.
The price is €210
includes taxes & fees
16 Nov - 17 Nov
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms

15. Carytown Family Home Free Parking Fenced Yard

Carytown Family Home Free Parking Fenced Yard
Byrd Park
9.2 out of 10, Wonderful, (23 reviews)
"Clean rooms and a very communicative host!"
United States
Kyla G.
The price is €227
includes taxes & fees
16 Nov - 17 Nov
Carytown Family Home Free Parking Fenced Yard

16. Oaks Retreat Carytown House Family Pet Friendly

Oaks Retreat Carytown House Family Pet Friendly
Randolph
9.0 out of 10, Wonderful, (20 reviews)
"Great quiet area, easy access to downtown and close to restaurants and parks. Nicely set up home with exceptional comforts for all"
United States
Thomas C.
The price is €239
includes taxes & fees
15 Nov - 16 Nov
Oaks Retreat Carytown House Family Pet Friendly

17. Adorable 2-bedroom house with AC in charming Richmond VA

Adorable 2-bedroom house with AC in charming Richmond VA
Richmond
10.0 out of 10, Exceptional, (2 reviews)
"Amazing hosts! Will highly recommend staying at this property"
United States
Shawn D.
The price is €191
includes taxes & fees
17 Nov - 18 Nov
Adorable 2-bedroom house with AC in charming Richmond VA

18. The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.

The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.
Davee Gardens
The price is €714
includes taxes & fees
15 Nov - 16 Nov
The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.

19. Walk to Allianz Urban Oasis in Oregon Hill

Walk to Allianz Urban Oasis in Oregon Hill
Oregon Hill
10.0 out of 10, Exceptional, (1 review)
"We really enjoyed our stay, Friday - Sunday. The apartment is exactly as shown in the photos, clean, comfortable and spacious. Street park was easily available and the location is good. Note: as stated in the description, the area is very close to VCU, lots of students living in the area. They were very loud on Friday and Saturday late night into the early morning... bring earplugs, it helps a lot."
United States
margaret
The price is €300
includes taxes & fees
15 Nov - 16 Nov
Walk to Allianz Urban Oasis in Oregon Hill
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesterfield Hotel Reviews

Find out more about Chesterfield

Chesterfield Holiday Homes information

Number of reviews
190
Accommodation
322 Holiday Homes
Lowest Price
€191
Highest Price
€763