Chesterfield Holiday Rentals from NZ$316: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Chesterfield has to offer?

Spacious 4-bedroom house in awesome Midlothian with AC : This holiday home rental outside of Chesterfield offers a fireplace, a BBQ 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 holiday 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.

includes taxes & fees

19 Oct - 20 Oct

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

2. Qualla Park

Chesterfield County

Shannon W.

includes taxes & fees

14 Oct - 15 Oct

A bedroom with a large bed, a chandelier, a window with curtains, and a painting on the wall.

3. Boutique 4 BR Stay/ 3 Kings/ Backyard/ Fireplace

Chesterfield

includes taxes & fees

16 Oct - 17 Oct

A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

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

Chester

Akia S.

includes taxes & fees

15 Oct - 16 Oct

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

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

Midlothian

includes taxes & fees

26 Oct - 27 Oct

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

Richmond

Allison K.

includes taxes & fees

22 Oct - 23 Oct

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

Chester

includes taxes & fees

15 Oct - 16 Oct

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

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

Richmond

Ashley Jo P.

includes taxes & fees

22 Oct - 23 Oct

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

Stephanie S.

includes taxes & fees

18 Oct - 19 Oct

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

10. Private bedroom and bath!

Midlothian

Ridge W.

includes taxes & fees

15 Oct - 16 Oct

A reception desk with a computer, a telephone, and a small plant.

11. 2 Queen Beds | Non-Smoking, Micfridge

Petersburg VA

Anonymous traveller

includes taxes & fees

14 Oct - 15 Oct

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

12. MV GiaMaria

Richmond

Jane

includes taxes & fees

16 Oct - 17 Oct

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

13. Cookie B

Richmond

Reshelle

includes taxes & fees

14 Oct - 15 Oct

A bedroom with a bed, a window with blinds, a door, and a carpeted floor.

14. River City Modern Retreat

Manchester

includes taxes & fees

9 Nov - 10 Nov

A room with a flat-screen TV mounted on the wall, a neon sign, a white cabinet with wine glasses, and a black cabinet with a white lamp.

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

Woodhaven

includes taxes & fees

14 Oct - 15 Oct

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

16. 1 King Bed | Non-Smoking, Micfridge

Petersburg VA

Anonymous traveller

includes taxes & fees

14 Oct - 15 Oct

A bedroom with a bed, a TV, and built-in shelving with decorative items.

17. Magnolias, a chill out place.

Richmond

Amir D.

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

18. 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.

includes taxes & fees

21 Oct - 22 Oct

A modern kitchen with a central island, white cabinetry, and a large window with a view of greenery.

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

Brandermill

includes taxes & fees

27 Oct - 28 Oct

A room with a fireplace, a mirror above it, and two leather chairs.

20. Nest & Rest | Private Studio | Free Parking

Fan District

Kelly M.

includes taxes & fees

20 Oct - 21 Oct

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Top Chesterfield Hotel Reviews

Comfort Suites At Virginia Center Commons

8/10 Good

"Very basic, No tissues in holder Table surfaces not clean in room Had to have my room key rescanned every night"

The Jefferson Hotel

10/10 Excellent

"I have never stayed at the Jefferson before, so I was knocked out by the room, the service, and the quality of everything. We had in-suite dining and were highly impressed by both the food and the promptness of delivery. The parking staff, bell hops, and doormen were outstanding. We were mightily impressed by the seamless connection among the parking folks, luggage delivery, and the front desk. Many other hotels could learn from this service! We were at the Jefferson for a Wedding Celebration...the cocktail party and the dinner were excellent! Having a gluten allergy, I was deeply appreciative of the staff's and chef's response to my needs--esp. given that we were with a group. Thank you!"

Find out more about Chesterfield

Everything you need to know about Chesterfield 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 holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. 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 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 holiday rentals we have selected for you start as low as NZ$316 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a holiday rental in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chesterfield has to offer?

Spacious 4-bedroom house in awesome Midlothian with AC: This holiday home rental outside of Chesterfield offers a fireplace, a BBQ 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 holiday rentals are there in Chesterfield?

Expedia has 6 holiday 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 holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for families.

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Check prices for these dates

Our top choices for Chesterfield holiday rentals

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

2. Qualla Park

3. Boutique 4 BR Stay/ 3 Kings/ Backyard/ Fireplace

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

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

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

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

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

9. The Birdhouse - Cozy Cottage Retreat in Richmond

10. Private bedroom and bath!

11. 2 Queen Beds | Non-Smoking, Micfridge

12. MV GiaMaria

13. Cookie B

14. River City Modern Retreat

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

16. 1 King Bed | Non-Smoking, Micfridge

17. Magnolias, a chill out place.

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

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

20. Nest & Rest | Private Studio | Free Parking

Find holiday rentals that suit your style

Top Chesterfield Hotel Reviews

Comfort Suites At Virginia Center Commons

Hilton Garden Inn Richmond Innsbrook

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

The Jefferson Hotel

Drury Plaza Hotel Richmond

The Commonwealth

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

The Berkeley Richmond, Outset Collection by Hilton

Find out more about Chesterfield

Frequently asked questions

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