Chesterfield Vacation Rentals from ￥27,061: Search Short-Term Rentals

Q: 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.

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In two weeks

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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.

Chesterfield

G H.

￥43,207 total

includes taxes & fees

Oct 25 - Oct 26

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

2. Qualla Park

Chesterfield County

Shannon W.

￥72,464 total

includes taxes & fees

Oct 25 - Oct 26

A marina with docked boats, a covered structure, and a forested hillside in the background.

3. A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

Richmond

Allison K.

￥33,311 total

includes taxes & fees

Oct 25 - Oct 26

A grand lobby with a large Christmas tree, marble columns, and a red carpeted floor.

4. A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

Richmond

Ashley Jo P.

￥33,311 total

includes taxes & fees

Oct 25 - Oct 26

A calm lake with a dock and a small building, surrounded by trees.

5. MV GiaMaria

Richmond

Jane

￥38,888 total

includes taxes & fees

Oct 24 - Oct 25

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

6. Newly finished basement suite in Midlothian. Very clean and spacious.

Midlothian

Jeannie C.

￥35,718 total

includes taxes & fees

Nov 1 - Nov 2

A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

7. Cookie B

Richmond

Reshelle

￥46,922 total

includes taxes & fees

Oct 25 - Oct 26

A two-story house with a front deck, a small porch, and a backyard with a trampoline and a grill.

8. Private bedroom and bath!

Midlothian

Ridge W.

￥36,620 total

includes taxes & fees

Oct 24 - Oct 25

A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

9. The Birdhouse - Cozy Cottage Retreat in Richmond

Swansboro West

paula S.

￥32,829 total

includes taxes & fees

Nov 2 - Nov 3

A gravel patio with a bench and two tables, surrounded by trees and a white fence.

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

Woodhaven

￥60,988 total

includes taxes & fees

Oct 27 - Oct 28

A hotel room with a bed, a wooden dresser, a television, a desk, and a chair.

11. 2 Queen Beds | Non-Smoking, Micfridge

Petersburg VA

Anonymous traveler

￥11,958 total

includes taxes & fees

Oct 25 - Oct 26

A bedroom with a bed, a ceiling fan, a window, and a bathroom with a sink and cabinet.

12. River City Modern Retreat

Manchester

￥36,280 total

includes taxes & fees

Oct 27 - Oct 28

A modern kitchen with stainless steel appliances, a white countertop, and pendant lighting.

13. Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Richmond

Dillon D.

￥51,298 total

includes taxes & fees

Oct 26 - Oct 27

14. Cozy “Brick Beauty”Richmond..FullBd-1 bath,Roof Pool,VCU, walkable neighborhood

Downtown Richmond

Andrea H.

￥38,510 total

includes taxes & fees

Oct 24 - Oct 25

A wooden gazebo with a bench and string lights, surrounded by trees.

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

Broad Rock

"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...

Stacie C.

￥57,497 total

includes taxes & fees

Oct 27 - Oct 28

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.

16. Lovely 2 Bedroom in the Heart of The Fan

Fan District

Nancy D.

￥55,989 total

includes taxes & fees

Oct 26 - Oct 27

A gray sectional sofa with patterned cushions, a white door, decorative wall art, a window with blinds, and a small table with a lamp.

17. The Fan Comfort Stay near VCU Free Parking Fenced Yard

Fan District

Katelyn F.

￥31,288 total

includes taxes & fees

Oct 25 - Oct 26

A living room with a fireplace, two grey sofas with yellow pillows, a flat-screen TV above the fireplace, and a large plant to the left.

18. Stylish 1BR Apt w/ King Bed, Free Parking & 1.5 Baths

Fan District

Brent W.

A living room with a sectional sofa, a flat-screen TV, a ceiling fan, and a modern chandelier.

19. Charming 1-bedroom suite with WiFi and AC in Bon Air

Bon Air

Jessica H.

￥46,903 total

includes taxes & fees

Oct 28 - Oct 29

A modern kitchen with a central island, stainless steel appliances, and bar stools.

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

Church Hill

Nello D.

￥30,178 total

includes taxes & fees

Oct 25 - Oct 26

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Top Chesterfield Hotel Reviews

Holiday Inn & Suites Richmond West End

10/10 Excellent

"Clean roon"

Holiday Inn Express Richmond I-64 Short Pump Area by IHG

10/10 Excellent

"The property was in a very nice location with many shopping and restaurant choices. The staff was very friendly and answered all local questions with good information. The breakfast area was very clean and the food was good. There was plenty of parking and most important the property was pet friendly."

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

8/10 Good

"The staff were very helpful and considerate, the rooms were clean, parking was sufficient. I thought the bed was too hard. The thermostat did not work in our room which we did not know until our second night when we needed heat. The staff was willing to offer another room, but we decided we just needed a couple of more blankets and did fine. Nice place to stay and close to everything."

Wingate by Wyndham Richmond Short Pump

10/10 Excellent

"Great room! Very modern and had everything we needed, only thing was the ice machine on our floor was broken so we couldn’t use it and the bathroom could use small toiletries as soap for hand washing which there was none. Other than that it was a great comfortable stay and would definitely be back"

Find out more about Chesterfield

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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.

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Check prices for these dates

Our top choices for Chesterfield vacation rentals

1. Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

2. Qualla Park

3. A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

4. A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

5. MV GiaMaria

6. Newly finished basement suite in Midlothian. Very clean and spacious.

7. Cookie B

8. Private bedroom and bath!

9. The Birdhouse - Cozy Cottage Retreat in Richmond

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

11. 2 Queen Beds | Non-Smoking, Micfridge

12. River City Modern Retreat

13. Downtown Living in Richmond's Amazing Shockoe Bottom

14. Cozy “Brick Beauty”Richmond..FullBd-1 bath,Roof Pool,VCU, walkable neighborhood

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

16. Lovely 2 Bedroom in the Heart of The Fan

17. The Fan Comfort Stay near VCU Free Parking Fenced Yard

18. Stylish 1BR Apt w/ King Bed, Free Parking & 1.5 Baths

19. Charming 1-bedroom suite with WiFi and AC in Bon Air

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

Find vacation rentals that suit your style

Top Chesterfield Hotel Reviews

Holiday Inn & Suites Richmond West End

The Jefferson Hotel

Holiday Inn Express Richmond I-64 Short Pump Area by IHG

Microtel Inn & Suites by Wyndham Richmond Airport

Graduate by Hilton Richmond

Linden Row Inn

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

The Commonwealth

Wingate by Wyndham Richmond Short Pump

Find out more about Chesterfield

Frequently asked questions

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