Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chesterfield vacation rentals

A rural landscape with a dirt path, grassy areas, and a building with a green roof.

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)
"The location is beautiful! Kristina was very prompt in answering my questions and very accommodating. Wonderful stay."
United States
Connie D.
The price is SARĀ 422
SARĀ 991 total
includes taxes & fees
16 Nov - 17 Nov
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
Our new outdoor space has room for a fire pit, grill and smoker, and seating for six.

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.
The price is SARĀ 760
SARĀ 1,645 total
includes taxes & fees
16 Nov - 17 Nov
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.
The price is SARĀ 413
SARĀ 864 total
includes taxes & fees
21 Nov - 22 Nov
Newly finished basement suite in Midlothian. Very clean and spacious.
A modern living room with a sofa, armchairs, a round coffee table, a fireplace, and a TV mounted on the wall.

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.
Game Room + Yard: Updated House in Chester!
A modern living room with a sofa, armchairs, a round coffee table, a fireplace, and a TV mounted on the wall.

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

Game Room + Yard: Updated House in Chester!
3.0 star property
Chester
Game Room + Yard: Updated House in Chester!
A marina with docked boats, a covered structure, and a forested hillside in the background.

6. 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 SARĀ 432
SARĀ 768 total
includes taxes & fees
17 Nov - 18 Nov
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A dock with a boat, a wooden pier, and a house with a red roof in the background.

7. 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 SARĀ 801
SARĀ 1,041 total
includes taxes & fees
16 Nov - 17 Nov
MV GiaMaria
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

8. Cookie B

Cookie B
3.0 star property
Richmond
9.4 out of 10, Exceptional, (11 reviews)
"Loved exploring the boathouse and reading the stuff around it. Great area, and wonderful location."
United States
Ronald
The price is SARĀ 821
SARĀ 1,124 total
includes taxes & fees
16 Nov - 17 Nov
Cookie B
A grand lobby with a large Christmas tree, marble columns, and a red carpeted floor.

9. 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 SARĀ 432
SARĀ 768 total
includes taxes & fees
17 Nov - 18 Nov
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A kitchen with a marble island, two barstools, a stove, and various kitchen items on shelves.

10. 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 SARĀ 374
SARĀ 743 total
includes taxes & fees
25 Nov - 26 Nov
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.

11. 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 SARĀ 488
SARĀ 838 total
includes taxes & fees
16 Nov - 17 Nov
Private bedroom and bath!
A person in a blue shirt and black jacket walking through a doorway with a child in a red shirt and black shorts.

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
The price is SARĀ 274
SARĀ 301 total
includes taxes & fees
14 Dec - 15 Dec
2 Queen Beds | Non-Smoking, Micfridge
A person in a blue shirt and black jacket walking through a doorway with a child in a red and black shirt.

13. 1 Queen Bed|Smoking,Kitchen

1 Queen Bed|Smoking,Kitchen
Laurel
10.0 out of 10, Exceptional, (4 reviews)
"Stayed one night, room was clean with essentials including a coffee machine ready right from check-in."
United States
Anonymous traveler
The price is SARĀ 209
SARĀ 242 total
includes taxes & fees
15 Dec - 16 Dec
1 Queen Bed|Smoking,Kitchen
A hallway with a white door at the end, a dark wooden floor, and a blue cabinet to the right.

14. 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 SARĀ 220
SARĀ 302 total
includes taxes & fees
23 Nov - 24 Nov
Cozy studio apartment in tranquil Richmond with heat and gym access
A two-story brick house with a porch, a small deck, and a garage.

15. 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.
The price is SARĀ 243
SARĀ 415 total
includes taxes & fees
20 Nov - 21 Nov
Magnolias, a chill out place.
A corner building with large windows and a black awning.

16. City Arts District in Downtown VCU MCV

City Arts District in Downtown VCU MCV
Downtown Richmond
9.8 out of 10, Exceptional, (34 reviews)
"Great place to stay! Walkable shops around. Will definitely stay here again."
United States
Yvonne V.
City Arts District in Downtown VCU MCV
Bright modern hallway with wood floors, storage, and bedroom access

17. River City Modern Retreat

River City Modern Retreat
Manchester
The price is SARĀ 470
SARĀ 912 total
includes taxes & fees
16 Nov - 17 Nov
River City Modern Retreat
A living room with a beige sofa, a round black coffee table, a large window, and a painting of a tree.

18. 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 SARĀ 750
SARĀ 1,595 total
includes taxes & fees
16 Nov - 17 Nov
Charming 3-bedroom townhome with WiFi in delightful Richmond
A wooden deck with white railings, a metal chair with a red cushion, and a metal basket.

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

Serene 6-bedroom house with AC in charming Midlothian
Brandermill
The price is SARĀ 1,783
SARĀ 3,516 total
includes taxes & fees
14 Dec - 15 Dec
Serene 6-bedroom house with AC in charming Midlothian
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, (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 kidsā€™ 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 SARĀ 683
SARĀ 1,406 total
includes taxes & fees
19 Nov - 20 Nov
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 Hotel Reviews

A modern living room with a sofa, coffee table, and bookshelves.
Country Inn & Suites by Radisson, Richmond I-95 South, VA

Country Inn & Suites by Radisson, Richmond I-95 South, VA

Country Inn & Suites by Radisson, Richmond I-95 South, VA
Bellwood

10/10 Excellent

Desk person very friendly and helpful! Didn't like first floor curtains not light blocking, every car brightness and outside lights lit up the room. 2 layers one sheer and one was supposed to be room darkening but wasn't and we felt with lights people could see in the room.
United States
Judy
Reviewed November 27, 2023
Country Inn & Suites by Radisson, Richmond I-95 South, VA

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.