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Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

PRIVATE 2 BEDROOM w/ BATH/SHOWER COMBO - Chesterfield, VA

2.0 star property
Hampton Park
The price is NZ$167
includes taxes & fees
23 Nov - 24 Nov
PRIVATE 2 BEDROOM w/ BATH/SHOWER COMBO - Chesterfield, VA

Cozy Custom Offgrid RV in brilliant Chesterfield with AC, Heat and WiFi

2.0 star property
Chesterfield
The price is NZ$295
includes taxes & fees
10 Nov - 11 Nov
Cozy Custom Offgrid RV in brilliant Chesterfield with AC, Heat and WiFi

Cookie B

3.0 star property
Richmond
9.6 out of 10, Exceptional, (7)
"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 NZ$353
includes taxes & fees
19 Nov - 20 Nov
Cookie B

MV GiaMaria

3.5 star property
Richmond
9.2 out of 10, Wonderful, (16)
"We liked the coziness of the boat, the views of the river, the surrounding areas were beautiful. The only negative thing we could say was that due to the ran/wind the boat creaked and it made it hard to sleep for one of our nights."
United States
warren
The price is NZ$382
includes taxes & fees
10 Nov - 11 Nov
MV GiaMaria

Cozy studio in FAN/museums /free parking

Fan District
9.6 out of 10, Exceptional, (27)
"Loved the apartment and the street of the house was so pretty. Great stay"
United States
Keylee R.
The price is NZ$238
includes taxes & fees
9 Dec - 10 Dec
Cozy studio in FAN/museums /free parking

Magnolias, a chill out place.

Richmond
9.4 out of 10, Exceptional, (19)
"Enjoyed my stay a lot! The property definitely has charm, the experience was very laid back. "
United States
Grace
The price is NZ$233
includes taxes & fees
1 Dec - 2 Dec
Magnolias, a chill out place.

Cozy nest/private porch/museums/free parking

Fan District
10.0 out of 10, Exceptional, (34)
"I would stay here again!"
United States
Darlene F.
The price is NZ$220
includes taxes & fees
10 Nov - 11 Nov
Cozy nest/private porch/museums/free parking

Charming 1-bedroom apartment in Mechanicsville

Mechanicsville
10.0 out of 10, Exceptional, (3)
"Had a great stay while fishing the james river. "
United States
Travis D.
The price is NZ$275
includes taxes & fees
10 Nov - 11 Nov
Charming 1-bedroom apartment in Mechanicsville

2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi

Fan District
10.0 out of 10, Exceptional, (5)
"This was a wonderfiul place to stay for our family. 2 adults and 2 teens. Check in was easy, the poperty owner was great. He answered all questions and was available anytime we needed something. The neighborhood it beautiful and quiet. Lots of museums, restaurants and things to do within walking distance. Parkiing is on the road and always alot of available spots. We will stay here again. "
United States
Michelle T.
The price is NZ$669
includes taxes & fees
10 Nov - 11 Nov
2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi

Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Richmond
8.6 out of 10, Excellent, (30)
"Loved it!"
United States
Christina B.
The price is NZ$424
includes taxes & fees
11 Nov - 12 Nov
Downtown Living in Richmond's Amazing Shockoe Bottom

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

Bon Air
10.0 out of 10, Exceptional, (7)
"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 NZ$552
includes taxes & fees
3 Dec - 4 Dec
Charming 1-bedroom suite with WiFi and AC in Bon Air

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

Richmond
9.4 out of 10, Exceptional, (225)
"Very peaceful. Lovely views"
United States
george j.
The price is NZ$395
includes taxes & fees
10 Nov - 11 Nov
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

Tourist Home of Richmond 1-bedroom Apartment - Church Hill North TH08

Richmond
10.0 out of 10, Exceptional, (1)
"Nice place with a comfy home feel very clean great spot despite the area not being the best being in the home made you not notice definitely five star location "
United States
Alex G.
The price is NZ$490
includes taxes & fees
11 Nov - 12 Nov
Tourist Home of Richmond 1-bedroom Apartment - Church Hill North TH08

Retro bungalow minutes away from historic Old Towne Petersburg!

Petersburg
9.0 out of 10, Wonderful, (8)
"Nice clean property just a shifty neighborhood"
United States
Kalayah
Retro bungalow minutes away from historic Old Towne Petersburg!

Luxe King Bd W Resort Amenities

Moseley
8.0 out of 10, Very good, (4)
"The location is easy if you don’t need to cross the river. The property is as displayed. However, there is no mention of extremely thin walls, lack of a storage place for either a hairbrush or a T-shirt. The kitchen has the basics, but don’t expect more. This is a place that may be comfortable with Millennials, who don’t really cook, y expect everything fast. The furniture is disposable and not the least comfortable. The host, I believe is an agency, so no insider knowledge available., no...
United States
Sissy S.
The price is NZ$400
includes taxes & fees
24 Nov - 25 Nov
Luxe King Bd W Resort Amenities

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

Richmond
9.6 out of 10, Exceptional, (112)
"Thank you for an amazing and peaceful experience "
United States
Jam 4.
The price is NZ$395
includes taxes & fees
10 Nov - 11 Nov
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

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

2.0 star property
Petersburg
9.4 out of 10, Exceptional, (3)
"The property was exactly as listed. Very responsive communication from the owner."
United States
Andrew W.
The price is NZ$634
includes taxes & fees
10 Nov - 11 Nov
Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience

Downtown Living in Historic Richmond Loft

Downtown Richmond
8.2 out of 10, Very good, (62)
"We were in Ohio for our granddaughters graduation. It was a quick trip up but we wished we could have stayed longer. The house was exactly what we needed! It is a beautiful property that is beautifully appointed. It was exactly what we needed!!"
United States
Wanda B.
The price is NZ$555
includes taxes & fees
1 Dec - 2 Dec
Downtown Living in Historic Richmond Loft

Sunny, Spacious Suite Green & Shaded Backyard

Northern Barton Heights
10.0 out of 10, Exceptional, (2)
"The apartment was perfect. Awesome location! Easy to get downtown and surrounding areas. The host was very responsive and diligent. Community pool was one block away, with 20 tennis courts and playground. Had a wonderful time visiting my family. Thank you. "
United States
Robin C.
The price is NZ$490
includes taxes & fees
18 Nov - 19 Nov
Sunny, Spacious Suite Green & Shaded Backyard

Private Guest house with Parking and Wi-Fi in a Central Location

Virginia Union
10.0 out of 10, Exceptional, (3)
"A perfect VRBO: clean, tastefully decorated, great location, safe, comfortable bed, great communication, and an overall warm welcoming feel. I would love to stay in Amanda’s VRBO again when visiting Richmond."
United States
Sandra D.
The price is NZ$474
includes taxes & fees
1 Dec - 2 Dec
Private Guest house with Parking and Wi-Fi in a Central Location
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

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$295 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?

Stylish retreat in charming Richmond with Private Sauna and other modern touches: 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. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chesterfield?

Expedia has 7 holiday rentals for your stay in Chesterfield.

What can I see and do in Chesterfield?

While exploring the area, visit family-friendly sights like Iron Bridge Sports Park, or get outside and enjoy nature at Appomattox River. Castlewood and Pocahontas State Park 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.