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Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

Holiday Rentals in Chesterfield

1 bedroom, free WiFi, bed sheets
Cozy Custom Offgrid RV in brilliant Chesterfield with AC, Heat and WiFi
Cozy Custom Offgrid RV in brilliant Chesterfield with AC, Heat and WiFi
2.0 star property
The price is AU$257
includes taxes & fees
18 Oct - 19 Oct
Cozy Custom Offgrid RV in brilliant Chesterfield with AC, Heat and WiFi
Fridge, microwave, oven, stovetop
The Studio@ Eanes Drug
The Studio@ Eanes Drug
10.0 out of 10, Exceptional, (41)
"Amazing, awesome and convenient place to stay in Richmond. "
The price is AU$278
includes taxes & fees
2 Nov - 3 Nov
The Studio@ Eanes Drug
Interior
Luxury Apt in Diamond District - Scott’s Addition
Luxury Apt in Diamond District - Scott’s Addition
6.0 out of 10, (1)
"The property was in a great location to the places we needed to be. We were disappointed that there was 1 bath towel, no wash clothes and two hand towels for our use. The listing stated two bedrooms, it was one bedroom with a pull out sofa however stated the unit slept 5. There were no sharp knives in the unit. I normally carry a ton of items and have gotten out of the habit as these are things that should be standard items in the units. "
The price is AU$290
includes taxes & fees
19 Oct - 20 Oct
Luxury Apt in Diamond District - Scott’s Addition
Marina
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
9.4 out of 10, Exceptional, (224)
"Captain Ron is one of the best hosts. Make sure you learn some local lore and history, too!"
The price is AU$344
includes taxes & fees
21 Oct - 22 Oct
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Interior
Landing Apartments near Virginia Union University
Landing Apartments near Virginia Union University
3.5 star property
8.8 out of 10, Excellent, (18)
"The neighborhood was quiet and it has nice food places around "
Landing Apartments near Virginia Union University
Smart TV, fireplace, computer monitors
Charming 1-bedroom suite with WiFi and AC in Bon Air
Charming 1-bedroom suite with WiFi and AC in Bon Air
10.0 out of 10, Exceptional, (6)
"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 "
The price is AU$328
includes taxes & fees
20 Oct - 21 Oct
Charming 1-bedroom suite with WiFi and AC in Bon Air
Fridge, microwave, oven, stovetop
Historic Haven in Church Hill
Historic Haven in Church Hill
10.0 out of 10, Exceptional, (36)
"Great place, great location!"
The price is AU$298
includes taxes & fees
9 Nov - 10 Nov
Historic Haven in Church Hill
Fridge, microwave, oven, stovetop
Lovely 2 Bedroom in the Heart of The Fan
Lovely 2 Bedroom in the Heart of The Fan
9.4 out of 10, Exceptional, (68)
"Super easy and beautiful location. Very clean inside! The bed could be a little more comfortable, but other than that, no complaints!! 10/10 exactly the spot we needed to stroll around Richmond for a few days. "
The price is AU$475
includes taxes & fees
19 Oct - 20 Oct
Lovely 2 Bedroom in the Heart of The Fan
Microwave, oven, paper towels
Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond
Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond
10.0 out of 10, Exceptional, (4)
"Great location. Nice apartment, owner very friendly and helpful."
The price is AU$463
includes taxes & fees
22 Oct - 23 Oct
Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond
Fridge, microwave, oven, stovetop
Stylish retreat in charming Richmond with Private Sauna and other modern touches
Stylish retreat in charming Richmond with Private Sauna and other modern touches
9.8 out of 10, Exceptional, (16)
"Great property- exactly what we needed for 2 families of 4 (4 kids under 10)"
Stylish retreat in charming Richmond with Private Sauna and other modern touches
Fridge, microwave, oven, stovetop
Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Living in Richmond's Amazing Shockoe Bottom
8.6 out of 10, Excellent, (30)
"This is a great location if you want a combination of touristy attractions and local dining/nightlife. Be aware that the street and parking lot outside will be active late into the night on weekends, but if you plan to go out yourself, you can’t ask for a better spot. "
The price is AU$366
includes taxes & fees
19 Oct - 20 Oct
Downtown Living in Richmond's Amazing Shockoe Bottom
Fridge, microwave, oven, stovetop
Carytown Home/Fenced Yard/3 TVs/Family-Friendly
Carytown Home/Fenced Yard/3 TVs/Family-Friendly
9.6 out of 10, Exceptional, (61)
"We were very comfortable here. It’s got that old school charm! The family loved walking to dinner and breakfast."
The price is AU$337
includes taxes & fees
21 Oct - 22 Oct
Carytown Home/Fenced Yard/3 TVs/Family-Friendly
TV, books, offices
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
8.4 out of 10, Very good, (8)
"Nice place and convenient location"
The price is AU$400
includes taxes & fees
20 Oct - 21 Oct
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
Exterior detail
Studio Nest/2Queen beds/2TVs museums/free parking
Studio Nest/2Queen beds/2TVs museums/free parking
10.0 out of 10, Exceptional, (49)
"My sister & I stayed here again after a wonderful experience last year. This place is a perfect location & comfortable accommodations. "
The price is AU$261
includes taxes & fees
21 Oct - 22 Oct
Studio Nest/2Queen beds/2TVs museums/free parking
Microwave, oven, stovetop, dishwasher
Luxe Modern Escape in Downtown Richmond - 2b2b
Luxe Modern Escape in Downtown Richmond - 2b2b
"Overall, our group had a pleasant time but there were a few things that effected our stay: We were given two different unit numbers for check-in, which caused some minor confusion. The apartment was not as clean as we would have liked; the toilet bowls were pink, the washer clearly has mold growing inside it, and most of the floors could have done with a good vacuum mopping. There was a sign in the living room clearly meant to display internet info, but it was left completely blank and we had...
The price is AU$738
includes taxes & fees
18 Oct - 19 Oct
Luxe Modern Escape in Downtown Richmond - 2b2b
Outdoor dining
The Sweet Family retreat/Fenced & Free Parking
The Sweet Family retreat/Fenced & Free Parking
9.6 out of 10, Exceptional, (50)
"Easy clean and comfortable "
The price is AU$467
includes taxes & fees
20 Oct - 21 Oct
The Sweet Family retreat/Fenced & Free Parking
Interior
NEW! Upscale Escape | Game Room & Spa-Like Baths
NEW! Upscale Escape | Game Room & Spa-Like Baths
9.4 out of 10, Exceptional, (6)
"We enjoyed our stay here with family. The home is beautiful and welcoming! "
NEW! Upscale Escape | Game Room & Spa-Like Baths
Fridge, microwave, oven, stovetop
Spacious Carytown Home: 6BR, Free Parking!
Spacious Carytown Home: 6BR, Free Parking!
2.0 star property
10.0 out of 10, Exceptional, (6)
"Don’t just look book lol, we enjoyed our stay will stay again"
The price is AU$896
includes taxes & fees
26 Oct - 27 Oct
Spacious Carytown Home: 6BR, Free Parking!
Terrace/patio
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
9.8 out of 10, Exceptional, (127)
"Everything you need for a stay in Richmond, especially if you have family at VCU. "
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
Smart TV, fireplace
Pet-Friendly 3BR Near Short Pump + Big Fenced Yard
Pet-Friendly 3BR Near Short Pump + Big Fenced Yard
9.4 out of 10, Exceptional, (3)
"The house was just what we needed. It is located close to I-64, so you hear some traffic noise, but it was not a problem. And it is very convenient to Short Pump and Broad St. Excellent communication with Maryam. We would stay there again. "
Pet-Friendly 3BR Near Short Pump + Big Fenced Yard
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

Comfort Suites At Virginia Center Commons

Comfort Suites At Virginia Center Commons

10/10 Excellent
"The front desk was friendly and helpful. "
Curtis 1-night trip
Posted 23 hours ago
Comfort Suites At Virginia Center Commons

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 favourite 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 depend 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 AU$257 per night. Entering your travel dates in the search wizard might find you 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. 

Explore a world of travel with Expedia

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.