A pathway through tall grass with the sun setting in the background.

Chesterfield County Holiday Rentals

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Our top choices for Chesterfield County holiday rentals

A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

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, (5 reviews)
"Cute place. Very spacious and clean. Great communication. Would definitely stay again. Thank you!"
United States
Jeannie C.
The price is HK$777
HK$1,752 total
includes taxes & fees
18 Oct - 19 Oct
Newly finished basement suite in Midlothian. Very clean and spacious.
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, (5 reviews)
"The home was beautiful and amazing! Host was amazing too! Highly recommend!"
United Kingdom
Shannon W.
The price is HK$1,412
HK$3,206 total
includes taxes & fees
29 Sept - 30 Sept
Qualla Park
A modern kitchen with granite countertops, stainless steel appliances, and dark wooden cabinets.

3. Luxe King Bd W Resort Amenities

Luxe King Bd W Resort Amenities
Moseley
9.4 out of 10, Exceptional, (12 reviews)
"Could use a comfier couch facing the TV other than that nice spot"
United States
Keith D.
The price is HK$650
HK$1,592 total
includes taxes & fees
29 Sept - 30 Sept
Luxe King Bd W Resort Amenities
A modern kitchen with a central island, white cabinetry, and a dining area with a table and chairs.

4. 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, (24 reviews)
"Great host and close to everything!"
United States
Brian V.
The price is HK$1,961
HK$4,036 total
includes taxes & fees
29 Sept - 30 Sept
Midlothian 3 Bedroom getaway for up to 8 guests!
A rural landscape with a dirt path, grassy areas, and a building with a green roof.

5. 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.
The price is HK$741
HK$1,937 total
includes taxes & fees
29 Sept - 30 Sept
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
A two-story house with a front deck, a small porch, and a backyard with a trampoline and a grill.

6. 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.
Private bedroom and bath!
A white building with a wooden porch, a red door, and a staircase leading to the entrance.

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

Historic Vincent House - Luxury 5BR Retreat Near Richmond, Virginia - Sleeps 12
Midlothian
9.8 out of 10, Exceptional, (10 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
The price is HK$2,294
HK$5,214 total
includes taxes & fees
29 Sept - 30 Sept
Historic Vincent House - Luxury 5BR Retreat Near Richmond, Virginia - Sleeps 12
A modern kitchen with a stainless steel refrigerator, a microwave, and a built-in oven. There are bar stools and a large island with a sink.

8. Spacious 4-bedroom house in awesome Midlothian with AC

Spacious 4-bedroom house in awesome Midlothian with AC
Brandermill
6.0 out of 10, (7 reviews)
The price is HK$1,961
HK$4,803 total
includes taxes & fees
29 Sept - 30 Sept
Spacious 4-bedroom house in awesome Midlothian with AC
A modern living room with a grey sofa, a patterned rug, and a unique spherical light fixture.

9. 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 HK$967
HK$2,422 total
includes taxes & fees
29 Sept - 30 Sept
Charming 1-bedroom suite with WiFi and AC in Bon Air
A calm lake with a dock and a small building, surrounded by trees.

10. 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
The price is HK$1,674
HK$2,177 total
includes taxes & fees
1 Oct - 2 Oct
MV GiaMaria
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

11. 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
The price is HK$1,716
HK$2,348 total
includes taxes & fees
29 Sept - 30 Sept
Cookie B
A marina with docked boats, a covered structure, and a forested hillside in the background.

12. 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, (248 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 HK$902
HK$1,658 total
includes taxes & fees
29 Sept - 30 Sept
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A modern kitchen with a central island, stainless steel appliances, and bar stools.

13. 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, (99 reviews)
"Very clean, cozy and in an excellent location."
United States
Courtney W.
The price is HK$1,130
HK$1,470 total
includes taxes & fees
29 Sept - 30 Sept
The Studio@ Eanes Drug-Heart of the Historic District
A modern kitchen with white cabinetry, a stainless steel refrigerator, a built-in oven, and a microwave.

14. Historic Haven in Church Hill in The Heart of the Historic District

Historic Haven in Church Hill in The Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (80 reviews)
"Nice stay"
United States
Danelle B.
The price is HK$1,235
HK$1,591 total
includes taxes & fees
12 Oct - 13 Oct
Historic Haven in Church Hill in The Heart of the Historic District
A grand lobby with a large Christmas tree, marble columns, and a red carpeted floor.

15. 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, (124 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
The price is HK$902
HK$1,658 total
includes taxes & fees
30 Sept - 1 Oct
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
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.
The price is HK$1,581
HK$3,457 total
includes taxes & fees
5 Oct - 6 Oct
Charming 3-bedroom townhome with WiFi in delightful Richmond
A black door with the number 1920 above it, flanked by two wicker chairs with cushions, a potted plant, and a doormat.

17. Charming Fan District Getaway

Charming Fan District Getaway
Fan District
9.8 out of 10, Exceptional, (36 reviews)
The price is HK$2,580
HK$4,669 total
includes taxes & fees
29 Sept - 30 Sept
Charming Fan District Getaway
A house with a covered porch, outdoor seating, and a well-lit deck area.

18. Steel Magnolias Cozy Main Home in Amelia County

Steel Magnolias Cozy Main Home in Amelia County
Amelia Court House
9.6 out of 10, Exceptional, (15 reviews)
"I would highly recommend Jenny’s VRBO- the house was beautiful, clean, and she was incredibly welcoming and communicative! "
United States
Marissa H.
The price is HK$1,216
HK$2,271 total
includes taxes & fees
29 Sept - 30 Sept
Steel Magnolias Cozy Main Home in Amelia County
A modern living room with a teal sofa, a coffee table, and a TV on a stand. There is a 'WELCOME' sign on the wall and a framed picture above the sofa.

19. 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, (88 reviews)
"Great location and very walkable to restaurants, shopping and museums."
United States
Nancy D.
The price is HK$898
HK$2,623 total
includes taxes & fees
30 Sept - 1 Oct
Lovely 2 Bedroom in the Heart of The Fan
A wooden gazebo with a bench and string lights, surrounded by trees.

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

Private Garden Home w/ Large Fenced Yard + Gazebo
Broad Rock
10.0 out of 10, Exceptional, (4 reviews)
"Halfway point for our travels up north. Very clean, quiet, everything we needed!"
United States
Tammy K.
The price is HK$1,654
HK$3,181 total
includes taxes & fees
1 Oct - 2 Oct
Private Garden Home w/ Large Fenced Yard + Gazebo
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 County Hotel Reviews

Comfort Suites At Virginia Center Commons

Comfort Suites At Virginia Center Commons

10/10 Excellent
"Lot of space. I didn't feel Claustrophobic. Nice having places to sit other than on the bed."
jackie 3-night trip
Posted less than an hour ago
Comfort Suites At Virginia Center Commons